ETOOSINDIA F.T.R. BY N.J.

SIR
INDIA’S NO. 1 ONLINE COACHING

Single Choice Question Exercise

1. Identify the major product.

H 2SO4
  Pr oduct

(A) (B) (C) (D)

Ans. (A)
2. Predict the product when given compound reacts with LiAlH4 :

O O
C C
H OCH3
(A)

O
O
C O CH3
C O CH3
(A) (B)

O
C
H
(C) (D)

Ans. (C)
18
CO2H CH2 
H
3. + 18 

(A) ; Product (A) is :
CO2H CH2

O O
18
C O CH2 C O CH2
(A) (B) 18
C O CH2 C O CH2
O O

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18
O
O O
C O CH2
(C) (D) H O C C O CH2 CH2
C O CH2
18
O
Ans. (B)

O O NaBH4
4.  (P)

O
O 
LiAlH
 (Q)
4

Sum of number of 1° alcoholic groups in product (P) and (Q) is :

(A) 1 (B) 2 (C) 3 (D) 4
Ans. (D)

O LiAlH
4
(A)

5. xAc2O
O

(B)

x = moles of anhydride consumed

(A) 1 (B) 2 (C) 3 (d) 4
Ans. (C)

6. For the following reaction, select the statement that best describes the change.
RCH2OH + PCC [C5H5NH+ClCrO3–] 
(A) The alcohol is oxidized to an acid, and the Cr(VI) is reduced
(B) The alcohol is oxidized to an aldehyde, and the Cr(VI) is reduced
(C) The alcohol is reduced to an aldehyde, and the Cr(III) is oxidized
(D) The alcohol is oxidized to a ketone, and the Cr(VI) is reduced
Ans. (B)

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7. Two unknown compounds X and Y, both having molecular formula C4H8O, give following results with four
chemical tests.

Bromine Na metal Chro mic acid

Compound X decolou ris es b ubbles Orange to Green
Compound Y No reaction No reactio n No reaction

Compound X and Y respectively are :

O
(A) CH3 CH2 C CH3 ; (B) OH ;
O O
O
(C) ; (D) CH3 CH2 CH2 C H;
OH
O O
Ans. (B)
8. Give the major organic product of the following reaction.

O
(1)sodium acetylide

(2)H O,H  to neutralize
 Product
2

O OH HO

(A) (B) (C) (D)

Ans. (C)

OH OH

 (A) OH +OH
PCC (1)MeMgBr NaBH 4 ,EtOH
9.  (B) 
(2)H O 
(C)  (D)
H 3

Product (D) in above reaction is :

OH OH OH OH OH OH
OH
(A) (B) (C) (D)
OH

Ans. (B)

PBr3 Mg, ether

(A) (C) Grignard reagent

H 3O
10. Na2Cr2O7 
(D)   (3, 4-dimethyl 3-hexanol)
(B)
H2SO4

When Grignard reagent reacts with (B) product (D) will obtained. Reactant (A) of the above reaction is :
OH
(A) (B) OH (C) (D)
OH OH
Ans. (A)

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11. Ph CH2 CH K
CH3  C2 H5 Br
  (A)

OH
Product (A) in above reaction is :
(A) Ph CH2 CH CH3 , (inversion) (B) Ph CH2 CH CH3 , (retention)
OEt OEt
(C) Ph CH2 CH CH3 , (racemic) (D) Ph – CH = CH – CH3

OEt
Ans. (B)

O O
CH3 CO C OCH3 (i)LiAlH4
12. 
(ii)H2 O
 (A) ; Product (A) of the reaction is
(96%)

OH OH OH CH2 OH OH CH2OH O

(A) (B) (C) (D)

Ans. (C)
13. What is the major organic product of the following sequence of reactions ?
O

(CH3)2CHCH2OH  H2C CH2 

?
PBr3 Mg H3 O
  
OH OH
(A) (CH3)2CHCHCH 2CH 3 (B) (CH3)2CHCH2CH2OH (C) (CH3)2CHCH2CHCH3 (D) (CH3)2CHCH2CH2CH2OH
Ans. (D)

O CH2 OH

14. CH2 OH LiAlH 4 H 3O

(C) . Product C is :


CH CO2Et +
(A)  (B) 
H
CH3

O O
(A) (B)
CH2 CH OH CH CH2 OH
CH3 CH3

O O
(C) OH (D)
C CH3 CH2 CH2 OH

CH3
Ans. (B)

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O
O
O O
O O O O
15. 
(A)

(B)

(C)

(D)

CO2CH3
CO2CH3 CHO
CH2 OH CHO
Identify correct combination :
CH2 OH
(A) (A)= (B) B = NaBH4 (C) (C) = KMnO4 (D) (D) = H3O
CH2 SH
Ans. (D)

16. What is true for the equilibrium reaction ?

O O
CH3 C OH + CH3 
OH 
cat.
 CH3 C O CH3 + H2O

(A) The use of equimolar quantities of CH3OH and CH3COOH will give the greatest yield of the ester at
equilibrium.
(B) Removal of water will increase the amount of ester at equilibrium.
(C) Addition of CH3COOCH3 will cause the formation of an equal number of moles of water.
(D) Application of pressure increases the amount of ester at equilibrium
Ans. (B)
O
OH
Pbr3 Mg (1) V CH3 C Cl
W X (2) H O+ Y Z
17. ether 3
Na2Cr 2O7
V
Product Z of above reaction is :

O
O
O C CH3
O C CH3
(A) (B)

O O
O C CH3 O C CH3
(C) (D)

Ans. (B)

18. Find out the reaction in which obtained product give positive isocyanide test :
O O
(A) LiAlH4 (B) NaBH 4
NH2  NH2  

NH LiAlH4
NH NaBH 4
(C)   (D)  
O O
Ans. (A)

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O OH
O O

19. H

O O

In the above given compound how many functional group reduced by LAH (Lithium aluminium hydride) and
SBH (sodium borohydride) respectively ?
(1) 4, 4 (2) 4, 2 (3) 3, 4 (4) 4, 2
Ans. (B)
20. Correct order of dehydration of following alcohols will be :

OH OH OH OH

1 2 3 4

(A) 1 < 2 < 3 < 4 (B) 4 > 3 > 1 > 2 (C) 4 > 2 > 1 > 3 (D)1 > 3 > 4 > 2
Ans. (C)

OH OH

Et Me

+
21. H ? product is :

Et Me

(A) (B)

Me O O Et

Et Me

(C) (D)

Ans. (D)
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Mg Hg Conc. H2SO4
Q.22 2Ph C CH3 Product
H 2O 
O

The main products is :

(A) Ph C C Ph (B) CH 3 C C CH 3
O O O O

Ph Ph
(C) Ph C C CH3 (D) Ph C C CH3
O O
CH3 CH3

Ans. (C)

CH3 CH3

Q.23 H3C C CH CH2 H3C C CH CH3 , This interconversion can be achieved by :

CH3 CH3 OH

(A) Acid catalysed hydration (B) Oxymercuration-demercuration

(C) Hydroboration - oxidation (D) Any method mentioned above
Ans. (B)
24. Which of the following ethers is the most unreactive to eleavage with conc. HBr ?
(A) Ph–CH2–O–CH3 (B) Ph–O–Ph

O O
(C) (D)

Ans. (B)
25. Consider the reaction of HI with the following :

(I) (II)
O

which forms di-iodide on reaction with HI (excess)?

(A) I and II both (B) II only (C) I only (D) none
Ans. (C)

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Br
Mg (i) 14CO2 NaHCO3
26 (A) (B) (C) gas, product C is :
(ii) H+/H2O

(A) CO (B) 14CO2 (C) CO2 (D) A mixture 14CO2 and CO2
Ans. (C)

27. SOCl2 Mg. O

OH 
Product
Pyridine Et2O
O H 3O

Product of reaction is :

O
OH CH3
(A) (B) CH C
O CH3
O

CH3 OH
(C) (D)
O CH2 C CH2 OH CH2 CH2 C CH3
O
CH3 CH3

Ans. (D)
O
O
Br2/h Mg. 1. Conc.H2SO4 O3
28. A B C D E
Et2O 2. H3O
+ Zn/H2O

Find out the structure of ‘A’ :

CH3

(A) (B) (C) (D)

Ans. (C)

COOH MgBr

29. + X+Y

(1 eq.)
SO3H

X and Y are respectively :

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COOH MgBr

(A) only (B) and

SO3H
COOH

(C) and (D) None of these

SO3MgBr


Ans. (C)
O
PhMgBr (excess)
30. Cl C Cl (X) ; Product (X) is :
H 3O +

O O O
OH
O
(A) Ph C Cl (B) Ph C Ph (C) Ph C Ph (D) Ph C Ph
Ph

Ans. (C)

SH
SH
OC2H5 (1) 'X' CH3MgBr
31. HO
HO
O HO

(A) 2 (B) 3 (C) 4 (D) 5

Ans. (C)

MgBr THF+ (X)

+ BrMg H3O

32.
O

Identify (X) :

(A) (B)
OH
OH O
HO

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OH
(C) (D)

HO O OH

Ans. (A)
33. Predict the reducing agents in following reaction.

H
O ?
OH

(A) LiAlH4 (B) NaBH4 (C) H2 / Pt,  (D) Both (A) and (B)
Ans. (C)
34. Predict major organic product from the following reaction:

H3C O NaBH4
A

LiAlH4
B
O

OH OH O OH
OH OH O OH
(A) A B (B) A B

O OH OH OH

OH OH O
OH
OH O
O OH
(C) A B (D) B
A

OH OH OH
O

Ans. (B)

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35. In the given reaction

H3C (i) Hg(OAc)2/CH3OH

C CH CH3 [X] , [X] will be :
(ii) NaBH4, OH
H3C

OMe OMe
H3C C CH2 CH3 CH3
(A) (B) H3C CH CH
CH3
CH3

(C) H3C CH CH2 CH3 (D) H3C CH CH2 CH3

CH3 CH3

Ans. (A)
36. Find out correct product of reaction :

HBr
(Excess)

Br

(A) (B)
O OH Br

(C) (D)

Br Br Br OH
Ans. (B)

37. , S is :

OH
OH
OH
(A) (B) (C) (D) OH

Ans. (B)

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38.

Find out ‘A’ of the reaction

HO OH HO CH2 OH

(A) (B)

HO CH2 OH

(C) (D)

Ans. (C)

39. ; Products of the reaction are :

(A) Racemic mixture (B) Diastereomers (C) Meso (D) Optically pure
Ans. (B)

40. The conversion

O OH
H3C C CH2 CH2CO2CH3 H3C CH CH2 CH2 CH2OH

Can be effected using :

(A) LiAlH4 and then H+ (B) B2H6(THF) (C) H2 / Ni (excess) (D) All
Ans. (D)

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H3O+ HBr Mg / ether HCHO HI E;

41. CH3MgBr + A B C D
H3O+

Product E is

(A) (B)

I
CH3 CH2I CH2CH3

(C) (D)
I
I
CH3 CH3

Ans. (D)
H2O dil. H2SO4 H2
42. In the reaction sequence , CaC2 A B Ni C , true about the product C is
Hg+2

(A) Give yellow ppt, with NaOI

(B) Its final oxidation product is carbonyl compound
(C) Its final oxidation product is CO2 and H2O
(D) Its final oxidation product is CH3COOH with Cu(300°C)
Ans. (A)

CH3CH2OH
43. CH CH 2 H2SO4

CH2CH3
(A) (B) CH2 CH3
OCH2 CH3
OCH2 CH3

CH2CH3

(C) (D) CH CH3

OCH2 CH3
OCH2CH3

Ans. (A)
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H2O/H
44. 'X' ; Product ‘X’ will be

O O
CH3

(A) (B)

(C) (D) All of these

Ans. (A)

SOCl 2 Mg. O
45. Product
Pyridine, Et 2O H


O CH2OH

The final product is :

(A) (B)

(C) (D)

Ans. (B)
46. Select the major product of following reaction :

CH 3CH 2O

Cl

O O

(A) (B)

OCH2CH3

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OCH2CH3
(C) O (D)

Cl

Ans. (D)
47. Identify the final product of following sequence of reactions :

TsCl alc. KOH OsO4 HIO4

OH
Pyridine

(A) (B) H
O

(C) (D) OH
OH

Ans. (B)
48. The product of the reaction is :

O
1. KH
HS 2. H 2O

OH S O
S
(A) (B)

OH

(C) HS–(CH2)5–O–Et (D) HS (CH2)4 CH

OH

Ans. (A)
49. Identify the major product of reaction :
OH
TSCl KSH
Pyridine
D
H

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SH SH
(A) (B)
D D H
H

D
(C) (D) No reaction
H
Ans. (B)

50. Final product is ?

CH3 CH3
(A) (B) C C
H H

(C) (D)

Ans. (C)

18
O +
H3O
51. ; Major organic product

18 18 18
OH OH OH OH
18 18
O O O
(A) (B) (C) (D)

Ans. (D)
52. Phenol and ethanol are distinguished by the reaction with
(A) Red litmus (B) NaHCO3 (C) FeCl3 (D) Na
Ans. (C)
53. Which of the following reactions would give the best yield of t-butyl methyl ether ?
H 2SO4
(A) (CH3)3C –OH 
140 C
 (B) (CH3)3C–Br + CH3OH 

 
(C) (CH3)3C–Br + CH3O Na (D) (CH3)3C – OK + CH3Br 
Ans. (D)

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CH CH2
CH2CH3 C
OH

54. B A
CH2CH2 OH
CHCH3
OH

Select schemes A, B, C out of

(I) Acid catalysed hydration (II) HBO (III) Oxymercuration-demercuration
(A) I in all cases (B) I, II, III (C) II, III, I (D) III, I, II
Ans. (C)

CH3

TsCl KSH
H OH  (A)   Products
55.
Et
(1 mole)

(Assuming all the substrate convert into substitution products containing 0.05 mole of S-configuration) Calculate
the percentage of SN2 mechanism.
(A) 90% (B) 80% (C) 70% (D) 95%
Ans. (A)
(i )CH 3CN (i )RMgX
56. RMgX 
(ii )H 2 O
(A) 
(ii)H 2O
(B) , (B) will be

(A) 1° ROH (B) 2° ROH (C) 3° ROH (D) Alkene

Ans. (C)
57. The major products of following reaction sequence are :

OH OH
Ph H 2SO 4  I 
LiAlH 4 H
Ph  (1) (2)
 II 
(3)
III

O O
Ph
Ph
(A) I = Ph (B) I = Ph

Ph Ph
Ph Ph
(C) III = (D) III =

Ans. (B)

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
H /
58. 
Catalyst Product
OH

(A) (B) (C) (D)

O OH HO
HO

Ans. (C)

CH3
HI(cold)
O  A  B
59. conc.

A, B are

CH3
OH
OH
CH3
(A) H (B) C2H5I (C) CH3I (D)
H
(R)
(S)

Ans. (B)
60. The end product of following reaction is :

Me
Na Me-I
Dry Ether
(A)
H OH Ether
SOCl2 NaOMe (B)
Low Temp.
Et

Identify relationship between products ?

(A) Diastereo Isomers (B) Enantiomers
(C) Functional Isomers (D) Geometrical Isomers
Ans. (B)

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61. Which of the following is/are the proper sequence of reagents for the conversion

OH Ph
OH
OH

O
||
(A) 
PBr3 Mg/Et 2O
  Ph  C  H
  H2SO4
  OsO4
  
 H 2O

PCl3 PhMgBr Br2 alc.KOH PhCO3H

(B)         
H O 3 H O 3

O
||
(C)  CH3MgBr
  H 2SO 4
  Ph  C  H
OsO4 alkaline
  
H O  3

KMnO4 PhMgBr H2SO4 Cold alkaline

(D)  
H O
 
 
KMnO4 solution
3

Ans. (D)

62. Acetone (CH3COCH3) is the major product in :


H3O
I. CH2 = C = CH2   H 2SO4 /HgSO4
II. CH3C  CH  
BH3 .THF
III. CH3C  CH 
H 2O2 /OH

(A) I, II (B) I, III (C) II, III (D) I, II, III

Ans. (A)

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Multiple Choice Exercise

1. Which combination of reagents will not bring about the following conversion ?

Br

(A) MeMgBr/H  , H 2SO 4/ , HBr/H 2O 2,h  (B) MeMgBr/H  , H2SO 4/ , HBr

(C) MeMgBr/H  , HBr/CCl4 (D) HBr/H 2O2, MeMgBr/H 

Ans. (B,C,D)
2. Which of the following reactions proceeds with inversion of configuration ?

Me Me
Na CH3Br TsCl CH3ONa
(A) H OH (B) H OH

Et Et

Me Ph
PCl5 CH3ONa SOCl2 KCN
(C) H OH (D) H OH

Et CH3

Ans. (B, D)
3. Products obtained in the following reaction.

(i) CH3MgCl
O
(ii) NH4Cl

OH
(A) (B)
OH

(C) OH (D)
OH

Ans. (A, B, D)

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4. Which of the following are correct regarding the products of the given reaction

Me
Me
H CN aqueous acetone
H H
H
Cl

OCH3

Me Me Me

Me Me H Me
H H
CN OH CN HO CN
H H H H H H
H H

OH H H

OCH3 OCH3 OCH3

(X) (Y) (Z)

(A) only X and Z are formed (B) Y > Z (amount) (C) X > Y (amount) (D) Y > X (amount)

Ans. (B, D)

H H
TsCl NaBr
5.   X  Y. X and Y are :
Pyridine
CH3 OH

H H H Br H
H H
(A) X = (B) Y = (C) X = (D) Y =
||

CH3 OTs CH3 H OTs

CH3 Br
Ans. (A, B)

6. What are the possible intermediates of the following reaction which form during this reaction path way ?

H3PO4
 
Δ

(A) (B) (C) (D)

Ans. (A, B, D)

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7. Which of the following reaction are not feasible ?


(A) O N a + CH3Br  OCH3

(B) + RO– 

CH3 CH3

(C) CH3 Br + ROH  CH3 OR

CH3 CH3

 
(D) Br + RO N a  OR

Ans. (B, D)
8. What are the products expected in the following reactions ?
O O
CH2N 2
C6H5 – C – CH2– C – CH3
Ether
OCH 3 O O OCH3

(A) C 6H5 C = CH – C – CH 3 (B) C6H5 C – CH = C – CH3

OCH3 O O OCH3

(C) C6H5– C – CH – C – CH3 (D) C6H5– C – CH – C – CH3

CH2 CH2

Ans. (A, B)
9. The intermediate stages in the conversion

(CH3)2– C – C – (CH3 )2 CH3COC (CH3)3 are

OH OH

(A) (B)

(C) (D)

Ans. (A, B, C, D)

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OH
25°C (A)
Conc. Conc. H2SO4
10. H2SO4
at 100°C
100°C (B)

The compounds given are :

OH
SO3H
SO3H

(II)
(I)

Which of the following statements is/are correct ?

(A) Compounds (A) and (B) are (I) and (II), respectively.
(B) Compound (I) is the major product at lower temperature when the reaction is under kinetic or rate control.
(C) Compound (II) is the major product at high temperature when the reaction is under thermodynamically or
equilibrium control.
(D) Compound (II) is more stable.
Ans. (A, B, C, D)
11. Which of the following statements is/are correct ?
(A) 4-Chlorophenol (I) will dissolve in NaOH but 4-chloro-1-methyl benzene (II) will not.
(B) 4-Methyl benzoic (III) acid will dissolve in aq. NaHCO3 but 4-methyl phenol (IV) will not.
(C) 2, 4, 6-Trinitrophenol (V) will dissolve in aq. NaHCO3 but 4-methyl phenol (VI) will not.
(D) 4-Ethyl phenol (VII) will dissolve in aq. NaOH but ethyl phenyl ether (VII) will not.
Ans. (A, B, C, D)

12. Which of the following paths is/are feasible for the preparation of ether (A) ?

Me
(A) Path I: Ph + EtONa
Br
Me
(B) Path II: Ph + EtBr
Me
ONa
Ph
1. Hg(OCOCF3)2
OEt
(C) Path III: Ph + EtOH
2. NaBH4 (A)

1. Hg(OCOCF3)2
Me
(D) Path IV : Ph + EtOH
2. NaBH4

Ans. (B, C)

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13. Which of the following statements is/are correct about the following reactions ?

Cl OH
NO2 NO2
1. NaOH HNO3
Path (I)
2. H3O
 H2SO4
OH
NO2 NO2 O2N NO2
(A) (B)

Path (II) NO2

Cl (C)
O2N NO2
HNO3 1. NaOH
H2SO4 2. H3O


NO2

(A) Path I is feasible.

(B) Path II is feasible.
(C) PhCl cannot be trinitrated because Cl and two NO2 atoms deactivate the ring towards further SE reaction.
(D) 2,4-dinitrophenol can be nitrated because the two deactivating NO2 groups prevent ring oxidation.
Ans. (A, C, D)
14. Which of the following statements is/are correct ?
(A) The nitration of phenol is faster than phenyl acetate.

(B) The reaction of PhO– is faster than NC O with PhCH2Cl.

(C) Base-catalysed hydrolysis of p-nitrophenyl acetate is faster than phenyl acetate.

(D) Acid-catalysed esterification of PhOH is faster than p-nitrophenol with MeCOOH.
Ans. (A, B, C, D)
15. Phenol can be prepared by
(A) Hydrolysis of chlorobenzene with aqueous KOH solution.
(B) Heating sodium salicylate with (NaOH + CaO).
(C) Reacting cumene hydroperoxide with dil. H2SO4.
(D) Heating benzenediazonium chloride with dil. H2SO4.
Ans. (B, C, D)

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Hot HI Alc. KOH/

16. A(C5H10O) C5H10I2(B)
(Chiral ether)
2 4
1
5
3
(C)
(1, 3-Pentadiene)

The structure of (A) is :

O O
Me O
(A) (B) (C) (D)
O Me
Me Me
Et

Ans. (A)
17. What is the major product of the following reaction ?

NaBH 4
  product
CO2H

OH OH
O OH

(A) (B) (C) (D)

CO2H CH2OH CO2CH3

CO2H

Ans. (A, B)

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Single Choice Questions

O Cl O
O N 2H 4 /KOH/H 2O
  (A) ; Product A is :
1. (Wolf Kishner reduction)
major

NO2

Cl O
OH O
O
O
(A) (B)

NO2
NO2

Cl OH
O O

(C) (D)

NO2 NO2

Ans. (A)
O
C CH3 CH2 CH3

2.
 
CH2 CH2 NMe3 CH2 CH2 NMe3
Above conversion can be achieved by :
(A) Wolf-Kishner reduction (B) Clemmensen reduction
(C) LiAlH4 (D) NaBH4
Ans. (B)

O CH2 CH3
CH2 CH3 CH2 CH3
C CH3 (A)
Hg)
Zn(
l
HC
3. NH
2
NH
OH – 2
/ (B)
OH Cl Cl
OH (P) (Q) (R)

Identify product (A) & (B) from the given product P, Q, R :

(A) A = P, B = Q (B) A = Q, B = R (C) A = Q, B = P (D) A = R, B = P
Ans. (C)

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O
C CH3
Zn (Hg)
4. 
HCl
(A) ; Identify the A.

HO

CH2 CH3

(A) (B)
HO Cl

OH
(C) (D)
Cl

Ans. (B)
5. Increasing order of equilibrium constants for the formation of a hydrate :

O O O
O
NH2

NH2 O2N
(I) (II) (IV)
(III)

(A) IV < III < II < I (B) IV < III < I < II (C) I < II < III < IV (D) II < III < I < IV

Ans. (C)

HgSO4
6. C C OCH3 
dil.H2SO4
 (A) Product (A) is
Major product

O
(A) C CH2 OCH3 (B) C CH2 OCH3
OH

O
(C) CH2 C OCH3 (D) CH2 CH OCH3
OH
Ans. (C)

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H 3O 
7.   A  B . Compound (A) and (B) can be differentiated by :
O
(A) 2-4-DNP (B) Fehling solution (C) Lucas reagent (D) NaHSO3
Ans. (B)

OH
OH
OH OH
8. PCC (excess) 1 equivalent CH3MgBr NaBH4
(A) (B) +
(C) (D)
H+ H3O

Product (D) will be

OH OH
OH
CH CH3
(A) (B) OH

OH OH
OH
(C) OH (D)

Ans. (B)

9. Rank the following in order of increasing value of the equilibrium constant for hydration, Khyd. (smallest value first)

O
O
O (CH3)3CCC(CH3)3

(1) (2) (3)

(A) 1 < 2 < 3 (B) 3 < 1 < 2 (C) 2 < 1 < 3 (D) 2 < 3 < 1
Ans. (B)

+i ve Iodoform test

–ive Tollens test

10.
H2 O
C6H12O3 Positive Tollens test
drop of H2SO4
A

Compound (A) is :

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O O OCH3
(A) CH3 – C – CH – CH 2 (B) CH3 – C – C – CH3

O O
(C) CH3 – C – CH2 – CH – OCH3 (D) H – C – CH 2 – CH2 – CH – OCH 3

Ans. (C)

CH2
11. CH3 CH CH CH2 OH 
HCHO
(A) ; Product (A) is
TsOH, 

OH

CH3
Ph CH2 Ph CH Ph CH3
CH3 CH3 Ph
(A) (B) (C) (D)
O O O O O O O O

Ans. (B)
HgSO4
12. CH3  C  CH 
dil.H2SO4
 (A)

(1)BH 3 .THF
CH 3  C  CH 
(2)H O / HO 
 (B)
2 2

Product (A) and (B) is differentiated by :

(A) 2-4-DNP (B) NaOI (C) Na-metal (D) NaHSO3
Ans. (B)

HCN LiAlH4 NaNO2

13.  (A)  (B) 
HCl
(C)

End product (C) in above reaction is :-

OH
O O O OH CH
2

(A) (B) (C) (D)

Ans. (A)

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14. Which of the following pairs of reactants is most effective in forming an enamine ?

O
O
||
(A) CH3CH 2 CH[(CH3)2 CH]2 NH (B) + CH3 – NH – CH3

O
||
(C) (CH 3 )3 C CH  (CH 3 ) 2 NH (D) None of these form an enamine

Ans. (C)

OH

H3O
15.   Products ; Product of the reaction is / are :
O
O CH2

OH
OH

(A) (B) OH (C) HCHO (D) Both (A) and (C)

OH
OH
OH

Ans. (D)
16. Which of the following does not form a stable hydrate on addition of H2O ?

O
O O O
(A) Ph C C C Ph (B) O

(C) O (D)

Ans. (D)

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17. Consider the following sequence of reactions.

H
1.C 2 H 5 MgBr H 2SO 4 ,heat 1.O 3
Ketone A 2.H 2 O
 B 
 H 2O
C 
2.Zn,H 2O
 + O
O

The ketone (A) is

(A) (B) (C) (D)

O O O O
Ans. (B)
18. In the reaction,

EtONa/EtOH
+ CH3COCH3 
heat
 X , the product (X) is

H3C CH3 H3C CH3

OH
(A) (B)

CH3
CH3 C
(C) C (D)
CH3 CH3

Ans. (B)
19. Which of the following -keto carboxylic acid does not undergo decarboxylation on heating ?

CO2H
(A) (B)
O
CO2H O

CO2H
CH3
(C) (D) None of these
O
Br

Ans. (A)

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O
PCC H 2C  CHMgBr NH 4Cl/H2O
20. HOCH 2CH 2CH 2 C OCH 2CH 3  (A) 
(1molar equivalent)
(B)  (C)

O
KOH H3O (CH3 C)2 O

 H 2O
 (D)
Pyridine

Product (D) is :

O
O C CH3 O
(A) H2C CH CH CH2 CH2 C OH (B) H2C CH CH2 CH CO2H
OH
O O O
CH CH CH2 C O C CH3
(C) H2C CH2 (D) H2C CH CH2 CH CH2 C O H
OH OH
Ans. (C)
21. The final product of the following sequence of reaction is :

H3O 
Mg H2C  O
(CH3O)2CHCH2CH2CH2Br   
heat


O O
(A) CH 3O C CH 2CH2CH 2CH 2OH (B) CH3 C CH2CH2CH2CH2OH

O O O
(C) HC CH 2CH 2CH 2CH 2OH (D) HC CH2CH2CH 2CH

Ans. (C)
22. The amino ketone shown below undergoes a spontaneous cyclization on standing. What is the major product of
this intramolecular reaction ?
O

CCH3

CH2CHNH2

CH3

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O CH3

N
(A) (B)
CH3 CH3
CH3 CH3

N
(C) (D)
NH2 CH3
Ans. (D)

MgBr
NH4Cl HCl(conc.) KOH(4 molar)
23. O (N) 
H2O
(O) 
cold
(P) 
ethanol, 
(Q)

Product (Q) will be :

(A) (B) (C) (D) OH

Ans. (B)
O

NH 2 OH H LAH
24.  (A)  (B)  (C) ; Product (C) of the reaction is :

OH

(A) (B) (C) (D)

N N N O OH
N
H H H H

Ans. (B)

25. C N + CH3MgBr 

H O
NaOI
(A)  (B)  (C)
14 3

Product (A) and (C) is :

O O
14
(A) C CH3 ; CHI3 (B) C CH3 ; CHI3

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O
(C) C CH3 ; CHI3 (D) CH2 CHO ; CHI3
14 14

Ans. (C)

OH
PCC
(A)
26.
OH PCC
(B)

(A) and (B) is differentiated by :

(A) NaH (B) 2-4 DNA (C) Tollen’s reagent (D) NaHSO3
Ans. (C)
 NH2  NH 2 heat
27. CH2 CH2 CO2H 
BaCO 3
 A   B 
KOH
(C) , Product (C) obtained is :

CH2 CH2 CO2H

(A) CH3 – CH = CH – CH2 (B)

N NH2

(C) (D)

Ans. (C)

O O

KOH
28. + CH2 = CH – CH2 – Br   (A) ; Product (A) is :
(75%)

CH2 CH CH2
O O CH2 CH CH2 O O

(A) (B)

O O
O O

(C) (D)
CH2 CH CH2
CH2 CH CH2

Ans. (B)

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29. End products of the following sequence of reactions are :

1.I2  NaOH, 
 2.H 

3. 
C CH3

O O

(A) yellow ppt. of CHI3, (B) yellow ppt. of CHI3,

COOH CHO

O
COOH
(C) yellow ppt. of CHI3, (C) yellow ppt. of CHI3,
COOH

Ans. (C)

CO2Et
H3O 
30. 
 A ; Product obtained is :
EtO2C
O

O O OH
CO2Et
(A) (B) (C) (D) None of these

O
O O

Ans. (B)

NH 2OH H 2SO4 H3O CHCl3 

31. (A) 

(B)  (C)  (D)  (E) 
KOH, 
 CH 3  N  C

Ph Ph


SOCl 2 (i)PhMgBr (excess) H CH2I 2
(D)  (F) (ii)H 
(G) 

(H) 
Zn/Cu


Molecular weight of compound (A) is :

(A) 58 (B) 120 (C) 60 (D) 182

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Ans. (A)
32. Compound A and B, both were treated with NaOH, producing a single compound C.

O O
CH3 CH3

HO– Compound (C) is :

+ heat

OH OH

(A) (B)

O
O C – CH3

(A) (B)

O
O

(C) (D)

Ans. (A)

O O –
|| || HO / 
33. CH3 – C – CH2 – CH 2 – CH 2 – CH 2 – C – H (A) ; Product (A) is :
(73%)

O
O
C – CH3

(A) (B)

O
CH3
C – CH3
(C) (D)
CHO
Ans. (B)

34. Ph – CH = CHCHO + CH3CH = CHCHO

base (A)87% ; Product of this reaction is :
EtOH, 

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(A) Ph –(CH = CH)2 – CHO (B) Ph – (CH = CH)3 – CHO

(C) Ph – (CH = CH)4–CHO (D) Ph – CH = CH – CH = CH – CH3
Ans. (B)

10% NaOH H2
35. CH3CHO 5°C  Ni (A) ; Product (A) of the reaction is
(A) propanol (B) ethanol
(C) butanol (D) pentanol
Ans. (C)

O
||
LDA (A) ; Product A is :
36. CH3 – CH2 – I (major)

O O
|| ||
(A) (B)

O O
|| ||
(C) (D)

Ans. (B)

37. The reaction,

CHO
+ conc. NaOH , products Identify the product.
CHO

CH(OH)2
(A) (B) O
CH(OH)2
–
CH2OH COO
(C) (D)
– –
COO COO
Ans. (C)
38. Identify the principal product of the following reaction ?
CH2CH = O
NaOH
H2O + ?
ethanol, water, heat
CH2CH = O

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CH = O CH = O

(A) (B)
CH = O
OH O

(C) (D)
OH O
Ans. (B)

O O
39. CH3 – C – CH2 – CH2 – CH2 – CH2 – C – H
KOH

Number of intramolecular aldol condensation product is :

(A) 1 (B) 2 (C) 3 (D) 3
Ans. (C)

–
OH 
40. CH 3CH = CHCHO Aldol (A); Product A is :
condensation

(A) CH3(CH = CH)3CHO (B) CH3CH2CH2(CH = CH)2CHO

(C) CH3(CH2CH2)3 CH = CH – CHO (D) none is correct
Ans. (A)

OH

H+ O3 HO–
41. 
(A) Zn
(B)  (C) ; Product (C) is :

O
O

(A) (B)

CHO
(C) (D)
O
C – CH3
Ans. (C)

42. Which of the following reactant on reaction with conc. NaOH followed by acidification gives the following lactone
as the product ?

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O
C–OCH3 CO2H

(A) (B)

CO2H CHO

CHO CO2H

(C) (D)

CHO CO2H

Ans. (C)
O
43. (P)
KOH


KOH
(Q) 

 Ph–CH2–OH + Ph – CO 2

(R) 
O3
 P + Q, Structure of (R) is

CH3
(A) Ph – CH = CH – CH3 (B) Ph – CH = C
CH3
CH3 CH3
(C) Ph–C = CH–CH3 (D) CH3–C=CH2

Ans. (B)
44. The following reaction gives :

CHO

conc.NaOH
+ HCHO ?
OMe
OMe

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CH2OH CH2OH

(A) + CH3OH (B) + HCO2

OMe OMe
OMe OMe

COOH COOH

(C) + HCOOH (D) + CH3OH

OMe OMe
OMe OMe
Ans. (B)
45. Arrange these compounds in decreasing order of reactivity for the nucleophilic attack:
(I) Acid chloride (II) Aldehyde (III) Ketone (IV) Ester
Select the correct answer from the codes given below :
(A) I > II > III > IV (B) IV > III > II > I (C) III > II > I > IV (D) I > IV > II > III
Ans. (A)
46. In the given reaction

O O
[X] (i)LiAlH 4
CH3 CH2 C CH2 COOC2H5 [A] CH3 CH2 C CH2 CH2OH+C2H5OH
(ii)H2O/H

[X] will be :

CH3 OH CH3 OH
(A) HCHO (B) (C) (D) HCN
CH3 OH +H CH3 OH +OH

Ans. (B)

47. In the given reaction:


NH2 OH/H
C6H5 C H [X]

[X] will be:

(A) Only syn oxime (B) Only anti oxime
(C) Mixture of syn and anti oxime (D) Secondary amide
Ans. (C)

48. Number of aldol products (without counting stereoisomers) in the given reaction :

C6H5CHO + CH3 – CHO OH Product

will be :
(A) One (B) Three (C) Two (D) Four
Ans. (C)

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49. In the given reaction

OH
NaOH
X+Y CH3 CH CH CHO
5°C
CH3

(X) and (Y) will respectively be :

(A) CH3–CH2–CHO and CH3–CH2– CHO (B) CH3–CHO and CH3–CH2–CHO

CH3
(C) CH3–CHO and CH3–CHO (D) CH3–CHO and CH3 C CHO
CH3

Ans. (B)

50. Acetophenone can be obtained by the distillation of :

(A) (C6H5COO)2Ca (B) (CH3COO)2Ca

(C) (C6H5COO)2Ca and (CH3COO)2Ca (D) (C6H5COO)2Ca and (HCOO)2Ca

Ans. (C)

51. The given reaction :

(i) Zn
C6H5–CHO + Br–CH2–COOC2H5 CH CH CH COOC2H5
(ii) HOH/NH4Cl 6 5
(iii)

is known as :

(A) Perkin reaction (B) Knoevenagel reaction

(C) Reformatsky reaction (D) Claisen Schmidt reaction
Ans. (C)
52. The Product of the reaction :

O2N CHO + (C6H5 CH2CO)2O

C6H5 CH2COONa/

[X]
will be :

(A) C6H5 CH CH COOH (B) NO2 CH CH COOH

(C) C 6H 5 CH C COOH (D) NO2 CH C COOH

CH 3 C6H5

Ans. (D)

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53. In the given reaction :

NaBH4 (X) (i) BH3 (Y)

H2C O (ii) H2O/H+(excess)

(X) and (Y) are :

(A) CH2 OH and HOCH 2 O

(B) CH 3 O and HOCH2 O

(C) CH 2 OH and CH3 OH

(D) CH2 OH and CH3 O

HO

Ans. (C)
54. A compound with molecular formula C8H18O4 does not give litmus test and does not give colour with 2,4–DNP. It
reacts with excess MeCOCl to give a compound whose vapour density is 152. Compound A contains how many
hydroxy groups ?
(A) 1 (B) 2 (C) 3 (D) 4
Ans. (C)

55. O

(i) NaBH4
A+ B
(ii) H2O

Identify relationship between A & B Products ?

(A) Diastereoisomers (B) Enantiomers (C) Positional isomers (D) Identical
Ans. (A)

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56. In the reaction sequence

HSCH2CH2SH H2
O +
A Ni, heat B
H

The products (B) is :

(A) (B)
S

SH

(C) (D) S
SH

Ans. (B)
57. Which of the following does not form a stable hydrate by the addition of H2O ?

O O O
(A) Ph C C C Ph (B)
O

(C)
O (D)

Ans. (C)
58. The conversion

O O
O

can be effected by using the reagent

(A) Tollen’s reagent (B) O3

Cl CO2H Cl CO3H
(C) (D)

Ans. (D)

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O O
NaOH
+ Cl2 P CH3COOH
59. (I) (II) + Cl2 Q

1 :1 1 : 1
(mole) (mole) (mole) (mole)

Organic product P & Q are respectively -

O O O O
Cl Cl Cl Cl

(A) , (B) ,

O O O O
Cl Cl Cl Cl

(C) Cl , (D) Cl , Cl

Ans. (C)
60. Total number of stereoisomers of major product (Q) are
NaOH 2CH3 CHO
CH3 CHO + 4HCHO -HCOONa (P) (Q)
H

(A) 0 (B) 4 (C) 8 (D) 2

Ans. (D)
61. The compound having the highest dipole moment is :

O
(A) (B) O (C) O (D)
O
Ans. (B)
62. Final product in the given reaction sequence is :
O
PhMgBr
+ [A] (i) H-C-H
H2
CH3 CH CH 
[B] [C]
(ii) H Pd/BaSO4

H
OH
(A) (B)
H H H OH

OH OH
(C) (D)
H H H H
Ans. (D)

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63. Consider the following reaction sequence.

1. O3 NaOH
A B
2. Zn.H2O heat

The products (A) and (B) are, respectively.

O
OH
(A) and
O
OH
OH
(B) and

OH
O
O

(C) and
O

O O
OH
(D) and OH
O O
Ans. (C)

64. Consider the following sequence of reactions.

O

HOCH2CH2OH 1. LiAlH4/Et2O
+ A + B
H 2. H 3O

COOCH3

The products (A) and (B) are, respectively.

O O
O O O

(A) and (B) and

O
COOCH3 CHO
CH3OC COOCH3
O

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O O O OCH2CH2OH OCH CH2

(C) and (D) and

COOCH3 CH2OH COOCH3 CH2OH

Ans. (C)
65. In the reaction
O O
Me

1. KOH. heat The product X is

2. H 3O+

Me COOH Me COOH

(A) (B)

HOOC HOH2C

HO COOH O

Me Me

(C) (D)

Ans. (C)
O
H
+
(i) N 2O 4
Q H3 O+ R
HCHO(excess)
S;
66. + C3H8O2 (leq.) P – Ba(OH)2
O optically inactive (ii) OH /
diol
Final product ‘S’ is -

OH

OH
(A) (B)

HO

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OH
OH
OH
(C) (D)

HO
Ans. (B)

O –
OH CH3 MgBr Zn-Hg
67. heat
A
CuBr
B
conc. HCl
C the product ‘C’ is
O

(A) (B) (C) (D)

Ans. (C)
68. Consider following intramolecular aldol condensation reaction :
O
–
OH
X ; X can be :


(A) (B)
O O O O
O O
(C) (D)
O O
Ans. (D)
69. CH3CH = CHCHO OH
–
 A, A is :
aldol

(A) CH3(CH = CH)3CHO (B) CH3CH2CH2(CH = CH)2CHO

(C) CH3(CH2CH2)3CH=CH – CHO (D) None is correct
Ans. (A)
70. Which one of the following will undergo aldol reaction most readily.

O O
O O
(A) (B) (C) (D)
O
O
Ans. (A)
O
H2 HCHO
71. Ph – C – Cl Ph – CHO (C) + (D)
Pd – BaSO4 ,KOH

Product (C) & (D) are :

(A) Ph–CO2H, Ph–OH (B) Ph  CO 2 , HCO 2

(C) Ph  CH 2 OH, H  CO 2 (D) Ph  CO 2 , CH 3OH

Ans. (C)

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CHO
conc. NaOH H+ (B)
72. (A)

CHO
Product (B) is

O O
O C CH2–O–C
(A) H2C=CH–CO2H (B) CH2 CH2 (C) (D) H2C=C=O
CH2–O–C
C O O
O
Ans. (B)
+
Aq. OH Conc. OH
73. PhCOCHBr2 A B H ; the compound ‘C’ is :

(A) PhCH(OH)CHO (B) PhCH(OH)COOH

(C) PhCOOH (D) None of these

Ans. (B)

O OH
-
A : Ph – C – CH = O B : Ph – C – COO C : Ph – CH – COOH
H OH
O O
NaOH KMnO4 NaOH/CaO
74. C C H A B C ; Product ‘C’ is
(conc.) 
O
CHO

(A) (B) (C) (D)

Ans. (A)

OH
A : Ph–CH–COONa B : PhCOOH C:

O
CCH
1% HgSO4/Dil.H2SO4 12/ NaOH 
75. +
X; X is :
H

O O O O
COOH COCH3 CH2CHO
(A) (B) (C) (D)

Ans. (D)

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O O O
C–CH3 COOH
HgSO4 I2/NaOH 
+
H2SO4 H –CO2

O
P2O5 (i) CH3MgBr (i) I2 + Ca(OH)2
76. C – NH2 A (ii) H O+ B (ii) C;
 3 
(iii) –CHI3

O O
(A) C – NH2 (B) C – OH

(C) C (D) C – CH2CH3

O O

Ans. (C)

O
A: CN B: C – Me

77. The major product pair of the following reaction will be :

CHO

HCHO Products
NaOH(aq)

COONa CH2OH

+ CH3OH + HCOONa
(A) (B)

CH2OH COONa

+ CH3OH
(C) (D) +
HCOONa

Ans. (B)

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78. Reactant ‘X’ will be :

CH 2OH
– +
COO Na
H+ O3
X Y Z1 + Z2 NaOH +
 Zn
OH/

Ph – C = CH – C – Ph
CH3 O

OH OH
(A) Ph – CH – CH – Ph (B) Ph – CH – CH – CH 3
CH 3 Ph

CH 3 OH OH
(C) Ph – CH – C – Ph (D) Ph – CH 2 – CH – Ph
CH 3
Ans. (A)
OH
X : Ph–CH–CH–Ph Y : Ph–C=CH–Ph Z1 : Ph–C–Me Z2 : Ph–CHO

CH3 OH O

79. Which is reduced during cannizaro’s reaction of HCHO & PhCHO with 50% conc. NaOH

(A) H C H (B) Ph C H
O O

(C) Both H C H and Ph C H (D) NaOH

O O
Ans. (B)
Mg  Hg conc.H 2SO4
80. 2Ph C C Ph 
H2O
 
Product

O O
The main product is :

Ph Ph
(A) Ph C C Ph (B) CH3 C C CH3 (C) Ph C C CH3 (D) Ph C C CH3

O O O O CH3 O O CH3

Ans. (C)

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81. Which of the following will not undergo Cannizaro reaction

CHO

(A) (B)
O CHO Cl

CHO
(C) (D) Cl3C–CHO

Ans. (D) Carbonyl

O3 conc.KOH

Zn
(A)  (B)
82. (1mole)

End product (B) of above reaction is

CHO CO2 K


(A) (B)
CH2OH CH2OH


CH2OH CO2 K
(C) (D)

CH2OH CO2 K

Ans. (B)

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83. Product obtained when benzoyl acetic acid is heated with soda-lime is

(A) COCH3 (B) COOH

(C) CH3 (D)

Ans. (A)
84. An aromatic compound ‘X’ (C9H8O3) turns blue litmus to red. It gives yellow precipitate with I2/NaOH and forms
Y(C8H6O4). Y forms three mononitro isomers. Identify X :

COCH3 COCH3 COCH3

COOH
(A) (B) (C) (D) None of these
COOH
COOH

Ans. (A)

COCH3

H OH
85. One mole of H OH was treated with NaOH/I2 and then acidified. The product after acidification has

NO2
COCH2I

isolated and then heated with 3 equivalents of NaOH to give a new ionic species. The ionic species formed will be:

COO COCH3 COO COO

(A) H O (B) H O (C) H O (D) H OH

H O H O H OH H O

NO2 NO2 NO2 NO2

COCH2I COO COO COO

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(i )Grignard reagent (excess)

86. Phenyl ester   'P ' , ‘P’ can be
(ii )H 

Ph Me Ph Ar Ph Me R R
(A) (B) (C) (D)
H OH Me Et R
OH OH OH
Ans. (D)
87. The end product of following reaction is :

O O
CH3MgBr 
PhMgBr H

(1)
 (2)
 
(3)
O

(A) -diketone (B) -Hydroxy acid (C) 1,2 - Diol (D) -Hydroxy ketone
Ans. (B)

(1)Mg  Hg conc.
88. 
(2)H 2O
 
H 2SO 4
 Major Product

O O

(A) (B)
O

O O

(C) (D)

Ans. (D)

Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 29
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Multiple Choice Questions
1. Two isomeric ketones, 3-pentanone and 2-pentanone can be distinguished by :
(A) I2/NaOH (B) NaSO3H (C) NaCN / HCl (D) 2,4-DNP
Ans. (A,B)
2. An optically inactive alcohol (A) C6H12O is oxidized by MnO2 to produce optically inactive carbonyl compound
while reduction of (A) by H2/Ni produces optically active compound. Possible structure(s) of alcohol is/are
(A) Hex-2-ene-1-ol (B) Hex-3-ene-2-ol
(C) 2-Methyl pent -2-ene-1-ol (D) 3-Methyl pent-2-ene-1-ol
Ans. (C,D)
3. Correct option(s) regarding following reaction sequence is/are :

HgSO4 Ba(OH)2 NaOH 6 Ag

CH3 C CH P Q R+S T
HgSO2 I2
'X'

COOH
(A) T is homologue of ‘X’ (B) R is sodium salt of

COOH
(C) P can produce S with NaOl (D) R is sodium salt of

Ans. (A,B,C)

(i) Ph3P
4. (A) CH CH3
(ii) BuLi
(iii) (B)
In above reaction (A) & (B) will respectively be

(A) Cl & CH3CHO (B) CH3CH2Cl & O

Cl
(C) & HCHO (D) Cl & CH3CHO
CH3

Ans. (A,B)
5. Correct option regarding following reaction sequence.
HgSO4 Ba(OH)2 NaOH
CH3 –CCH P Q R+S
'X' H2SO4  I2
6 Ag

T
COOH
(A) T is homologue of ‘X’ (B) R is sodium salt of

COOH
(C) P can produce S with NaOI (D) R is sodium salt of
Ans. (A,B,C)
O O O COONa
P : CH3–C–CH3 Q : CH3–C=CH–C–CH3 R: S : CHI3 T : HCCH
6. Which of the following compounds(s) give a sweet smelling product having anesthetic use in presence of Cl2,
NaOH, .
O

(A) (B) CH3 – CH – CH3

O I

O O
(C) CH3 – C – OH (D) Ph – C – CH 3
Ans. (A,B,D)

O O O O
Cl
 
Cl2 +NaOH OH ONa OH ONa
Cl
CHCl3+
Cl2 CCl3 ONa


O O
O O

7. In which reaction haloform is obtained as one product :-

(A) Electrolysis of ethanolic aqueous solution of NaCl
(B) Isopropanol with bleaching powder
(C) Chlorination of methane in sun light
(D) Chloral is treated with NaOH
Ans. (A,B,C,D)

3 ( i ) Ph P
8. (A)  
 
(ii ) BuLi
(iii ) ( B)
In above reaction (A) and (B) will respectively be

(A) & CH3CHO (B) CH3CH2Cl &

(C) & HCHO (D) & CH3CHO

Ans. (A, B)

9. Which of the following form stable hemiketal

O O
|| ||
(A) Ph  C  Ph (B) HO  (CH 2 ) 3  C  CH 3

O O
|| ||
(C) CH 2 OH  C  (CHOH)3  CH 2  OH (D) HO  CH 2  ( CH 2 ) 4  C  CH 3

Ans. (B, C, D)
10. Which of the following is example of 1,4-addition reaction

O
|| ( i ) NaCN
(A) CH 2  CH  C  H  
( ii ) H 2O

O
|| LAH
(B) CH 2  CH  C  H 

H 2O / H

CH ONa / CH OH
(C) + CH2(COOMe)2 3 3

H
3O

CH CH  CN
(D) 2  

Base

Ans. (A, C, D)

11. Which of the following statements are correct about the following reaction ?

Cl LAH
(B)
LBAH
O (C)
Lithium tri-t-butoxyaluminium
hydride [Li(O-t-Bu) 3AlH]

(A) The produces (B) and (C), respectively, are : Me2CHCHO and Me2CHCH2OH.
(B) The produces (B) and (C), respectively, are : Me2CHCH2OH and Me2CHCHO.
(C) LBAH is more reactive reducing agent then LAH.
(D) LBAH is less reactive reducing agent then LAH.
Ans. (B, D)
12. Which of the following reactions would give propanal ?
(A) Ethyl proponate + DBAH (diisobutyl aluminium hydride). [(i-C4H9)2AlH)] at –70°C, followed by hydrolysis.
(B) Propyl propanoate + DIBAL-H/H2O
(C) Ethyl cyanide + DBAH
(D) Propanoyl chloride + LBAH
Ans. (A, B, C, D)

13. Which of the following reactions are correct?

O
LDA
(A) Me + MeCHO 
THF
 One crossed aldol products

O 
OH
(B) Me + MeCHO   Two crossed aldol products

Me
(C) 3 O 
Conc.H SO

 Phorone
2 4

Me
 Me
Dry HCl
(D) 3 O   Mesitylene
Me
Ans. (A, B, C)

14. Which of the statements are correct about the internal or intramolecular Cannizzaro reaction given below ?

O OH
OH
2 1 –
Ph CHO Ph COO

(A) OH attacks at C– 1 of (CHO) group.

(B) OH attacks at C– 2 of (C = O) group.

(C) H– transfer takes place from C–1 to C–2.
(D) H ecxchanges from acid to alcohol ion.
Ans. (A, C, D)

15. Which of the following statements are correct about the reaction given below ?

O
HCN Sn  HCl HNO2

Traces of KOH
(B)  (C)  (D)
(A)
(A) In the formation of (D) from (C), ring expansion takes place.
(B) The product (D) is cyclopentanone.
(C) The product (D) is ,-unsaturated cyclopentanone
(D) Conversion of (B) to (C) can also be carried out with LAH.
Ans. (A, B, D)

16. Which of the following are Perkin reactions ?

NaOAc
(A) Me CHO + Ac2O

COOH
Me

O CHO
COONa
(B) Me CHO + O

O
COOH
Me
 COOEt
(C) Me CHO + R3N

COOEt

COOH
Me

COOMe
NH3/EtOH
(D) CHO +
COOEt

COOH

Ans. (A, B)
17. Which of the following are correct reactions ?
NO2
O+ OH
(A) Me NO2 
Me

NO2

(B) O+ OH
Me NO2  Me

?
CH3COO NH4
COOEt
(C) O + NC
COOEt

CN

?
CH3COO NH4
COOEt
(D) O + NC
COOEt

CN
Ans. (A, C)

18. Which of the following statements are true about the benzoin reaction ?

aq.alc.
O2N CHO + Me CHO 
KCN


(A) (B)
 (A) CN attack at the (C=O) group of (A)

(B) CN attack at (C=O) group of (B)

(C) The major product formed is

O2N Me

OH
(D) The major product formed is

OH

O 2N Me

O
Ans. (A, C)

19. Which of the following statements are correct about the following reaction ?

OH OH
H HNO2
 (C) 
OH NH2
(A) (B)
(A) In the formation of (C) from (A) or (B), expansion of ring takes place.
(B) In the formation of (C) from (A) or (B), contraction of ring takes place.

(C) Product (C) is CHO

CHO
(D) Product (C) is

Ans. (B, C)

Me O *


20.  (B)
Me Me
(A)
Which of the following statements are correct about the above reaction ?
(A) The reaction is called Claisen-Schmidt reaction.
(B) The reaction is called Claisen rearrangement reaction.

*
Me
(C) Product (B) is
Me
Me
O
 *
Me
(D) Product (B) is
Me
Me
O
Ans. (B, C)

21. Which of the following are correct products ?

O
Me 
NaNO2 Ac2 O
(B)  (C)
 HCl at 0°C
Ph
The products given are :
O
CH N OH
(A)
Ph
O
Me
Ph
(B)
N
OH

O
C N
(C)
Ph
O
Me
(D)
N
Ans. (B, D)
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Misc. Exercise
Subjective Type Questions

1. Predict the organic products :

CH2 CH2 CH2 NH2
O +
(i) H+/
(i) H /
(A) CH3 C CH3 + CH3 CH2 NH2 (B) (ii) H2/Pt
(ii) H2/Pt O

O
(i)Cl2 /NaOH/HOH
(C) C CH3  (ii)H


2. Identify A to E :

CH3 O

NaOH
(A) + (B)
Br2(leq)
(Structural isomer)
(i )
CH 2O/
(ii

3
M
)H

gB

(i) [SH 
r

SH
H

(ii) H2/Pt Conc. H2SO4/

(D) (E)

(C)

3. Complete reaction sequence :

(i) OH
(i) O3(leq) (i) OH
(I) (A) (B) (II) (ii) C 6H 5CHO Product
(ii) Zn/ H2O (ii) 
(iii) 
O

4. Complete the following reactions :

O OH O

CH 3 CH – CH 3
OH OH
(I) (X) + (Y) (II) (X)
CH3
OH

(i) OH
(III) [X]
(ii) 

(i) C 2H 5ONa
5. C6H5COOC2H5 + CH3COOC2H5 (ii) Acidification
D + D’
Ethyl benzoate
COOPh (i) PhONa
6. PhOOC F
(ii) Acidification

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CH 2CH 2COOEt 
(i) C 2H 5ONa H 3O
7. C 2H 5–N G H (Piperidone derivative)
CH 2 CH2COOEt
(ii) Acidification 

(i) (CH 3CH 2CO) 2 O/CH 3–CH 2–COONa,

8. H3 C CHO + A
(ii) H /H 2O, 

O
O C – Me
Et2NH
Ph – C – H + CH2 D
9. 
C – OEt
O

O
10. nC5H 11NH 2
Ph – C – H + CH3 – NO 2 E


CN O
NaOEt
11. CH 2 + Ph – C – H G

NO 2

O2 N Me

NO 2 + Ph – NO OH/ H
12.
O2N

O COOR
EtONa
CH – CH3 + CH2 +
?
(ii) H3O ,
13. COOR

O
(i) Zn
(ii) PhCHO
14. OEt  B
(iii) H 3O, 
Br

15. (i) Zn (i) 

+ BrCH2COOEt  D E
(ii) H3 O (ii) Se/

-Tetralone
Br
(i) Zn/Et2O (i) 
16. EtO – C – CH – CH2CH2CH2 – CH2 – CHO  F G
(ii) H3O (ii) Se/
O

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O O
OH
17. CH3 C – C – C6H5

OHO
Fenton (i) OH
18. C6H5 – C – CH – C6H5 A  B.
reagent (ii) HOH / H

O
19. (i) NaOH
(ii) H3O
O

Li Cul CH3CH2CH2CH2CH2I
20. CH3 – I (A) (B) (C)
Et2O  
Li Cul CH3CH2CH2CH2CH2Br
CH3CH2CH2CH2Br (D) (E) (F)
Et2O  

CH3 – CH – CH3
Cl
(C)

Li CuBr
21. CH3 – CH2 – Br (A) (B)
 O

(i)
(D)
(ii) H


H
22. (CH3)2 CuLi + CH3 – CH – CH 2 (A) (B)
O
23. How many of the following compounds will give iodoform test positive ?

O OH O

(a) OH (b) CH3 C CH3 (c) CH3 CH Ph (d) C

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OH O O
(e) (f) (g) CH3 C OH (h) CH3 C COOH
OH

O
O O O
(i) CH3 C OMe (j) (k) Et C CH2 C Et
O

(l) CH3 – CH2 – CH2 – OH (m) Ph – CH2 – OH

(i) NaOH 
24. Ph C CH O + A Products
(ii) H
O

What is the number of possible products ?

25. Number of compounds can be oxidised by Tollen’s reagent.

O
O
CH O O
CH
(i) (ii) H C OH (iii) (iv)
O

O
O OH OH O CH3
(v) (vi) CH2 C (vii) CH3 C (viii)
O CH3 CH2 OH
OH CH3 CH3
O

26. Number of reagents which converts CH3–CHO into carboxylic acid or its salt :
(1) Cu/573 K (2) Fehling’s reagent (3) Na/Liq. NH3 (4) Tollen’s reagent (5) NaOH/I2
+ +
(6) Bayer’s reagent (7) H /KMnO4/ (8) H2/Pd (9) H /K2Cr2O7/ (10) OH–/
27. The compound among following which can give 2, 4-DNP test (2, 4-dinitrophenylhydrazine test)

O
(1) (2) (3) (4)
O NH

NH2
O
(5) (6) (7) H (8) HCHO
O
O

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O H

(9) (10)

O
28. Consider all possible isomeric ketones including stereoisomers of MW = 100. All these isomer are independently
reacted with NaBH4 (Note : stereoisomers are also reacted separately). The total number of ketones that give a
racemic product(s) is/are :
29. Compound (A) (C6H12O2) on reduction with LiAlH4 yielded two compounds (B) and (C). The compound (B) on
oxidation gave (D) which on treatment with aqueous alkali and subsequent heating furnished (E). The latter on
catalytic hydrogenation gave (C). The compound (D) was oxidised further to give (F) which was found to be
monobasic acid (molecular mass = 60.0). Maximum number of CH3MgBr consumed by A, B, C, D are
Comprehension :
Paragraph -1 (30-32)
An alkene (A) C16H16 on ozonolysis gives only product (B) C8H8O. (B) can also be obtained by hydrolysis of the
product obtained by reaction between cyano benzene and CH3MgBr. (A) can show geometrical isomerism can it
can decolourise Br2 water. (B) on treatment with SeO2 produces (C).
30. Which is not correct about ( A ) ?
(A) A is optically in active
(B) On catalytic hydrogenation ‘trans’ from of A produces racemic mixture
(C) A can be prepared by Witting reaction on acetophenone with Ph3P = C(CH3)Ph.
(D) On treatment with per acid followed by hydrolysis ‘trans’from of A produces racemic mixture
31. Which is not correct about B ?
(A) It gives iodoform test
(B) On treatment with LiAlH4, H2O it produces a compound which also responds to iodoform test.
(C) It gives Tollen’s test
(D) On treatment with NH2NH2 followed by alc. KOH at high temperature, it produces ethyl benzene.
32 Which is not correct about C ?
(A) On treatment with NaBH4 it will produce a diol.
(B) On treatment with OH– (conc.) followed by acidification racemic mixture of a carboxylic acis is obtained.
(C) It gives Tollen’s test.
(D) It can take part in aldol condensation.
Paragraph - 2 (33-34)

A(Hydrocarbon) (C = 88.24%) [Molecular weight of A = 68]

(i) Na
A (ii) n-propyl bromide B(C8H14)
2+
Hg
A C5H6O (C)
dil. H2SO4
KMnO4
A + Carboxylic acid + Gas
H

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Q.33 ‘A’ can be :

(A) H3C–H2C–CC–CH3 (B) CH3–CH2–CH2–CC–H

CH3
(C) CH3 CH C CH (D)
CH 3

34. Correct statement reagarding C is.

(A) C reacts with fehling solution to give red ppt. (B) C gives +ve iodoform test
(C) C give -ve 2, 4 D.N.P test (D) C is aldehyde

Paragraph - 3 (35-36)
In given reaction sequence

(i) O3
(A) (B) + (C)
C10H20 (ii) Zn/H2O Racemic mixture
Optically of carbonyl compound
Inactive alkene
H2N OH
Br2
in CCl4
Oxime(s)
(D) + (E)
Mixture of two different
meso compounds

35. Alkene A is :

H H

(A) (B)
H
H

H H

(C) (D)
H
H

36. How many total oxime(s) is/are obtained :

(A) 1 (B) 2
(C) 3 (D) 4
Paragraph - 3 (37 to 39)
Observe the following reactions.

H2SO4 / 
H2SO4 (i)MeMgBr (1eq.) LiAlH4 (80 )
X (1)
 Y 
(ii)H (2)
 (Z)  (3)
(W) 
(4)  H2O

C6H12O2 Me O Me
(M.F.)

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37. The compound ‘X’ is

HO O
(A) COOH (B) COOH

Me Me

O COOH HO COOH
(C) (D)
Me Me

38. Compound ‘Y’ is

(A) (B)
Me O O Me O O

O COOH

(C) Me COOH (D)

Me

39. The correct statement about ‘Z’ and ‘W’ is

(A) Both give positive Tollen’s test (B) Both give positive iodoform test
(C) Both give positive test with 2, 4-DNP (D) W on CrO3 / H oxidation gives Z.
Match the Column
40. Match the reactions in Column -I with appropriate types of step/reactive intermediate involved in these reactions as
given in Column II
Column - I Column - II

H3 C O
O aq NaOH

(A) (P) Nucleophilic substitution

O
O

CH3MgI CH3
CH2CH2CH2Cl
(B) (Q) Electrophilic substitution

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18 O
O

18 H2 SO4
(C) CH2CH2 CH2OH (R) Dehydration

CH2 CH2CH2C(CH3 )2 H2SO4

OH
(D) (S) Nucleophilic addition
H3C CH3

(T) Carbanion
41. Match the column :
Column - I Column - II
(A) HCHO + NaOD (conc.) (P) DCOO– + CDH2OH
(B) DCHO + NaOH (conc.) (Q) DCOO– + CD2OH
(C) DCDO + NaOH (conc.) (R) DCOO– + CDH2OD
(D) DCHO + NaOD (conc.) (S) HCOO– + CH3OD
42. Column - I Column - II
(Reactions) (Intermediate formed or type of reaction)

O O
OH–
(1)  (P) Product obtained as racemic mixture

O
+ H
(2) OH OH O O (Q) Substitution reaction

+ conc. + conc.
HNO3 H2SO4
(3) (R) Nu– Addition takes place during reaction.
NO2

OH
O (1) LaH
(4) (S) Carbocation intermediate
(2) H2O

(T) Carbanion intermediate

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43. Match the columnn

Column - I Column - II

COOEt
(1)EtONa
(A) Ph CHO+ CH2 
(2)H O /  (P) Perkin’s reaction
3
COOEt

(1) Zn
(B) Ph CHO+ CH2 COOCH3 
(2)H3O /  (Q) Reformatsky reaction
Br

(1)CH 3COONa/ 
(C) Ph–CHO + CH3COOCOCH3 
(2)H 3O  / 
 (R) Product is a carboxylic acid with aromatic ring within

the same molecule.

O O
(D) Ph C C Ph +NaOH 
(2)H 

(S) Double bond equivalent of the product formed is less
than or equal to 8.
(T) The major product cannot show optical isomerism.

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SINGLE CORRECT EXERCISE (GOC)

1. (A) (B) (C)

Compare carbon-carbon bond rotation across A, B and C

(A) A > B > C (B) B > C > A (C) B > A > C (D) B > C > A

Ans. (C)

*
KH *
2. A + H2 ; (C = C14)
H2O
Major product

Major products of the reaction is (are) :

*
*
(A) (B) (C) (D) All
*
Ans. (D)

3. Among the isomeric amine select the one with lowest boiling point.

H CH3 NH2
N
N
(A) (B) NHCH3 (C) (D)

CH3

Ans. (C)

4. Which of the following, is the product of the reaction between AlCl3 and CH3OCH3?

Cl Cl
– + CH3 + – CH3
(A) Cl—Al— O (B) Cl—Al— O
CH3 CH3
Cl Cl

Cl Cl
+ + CH3 – +
(C) Cl—Al— O (D) Cl—Al— CH3OCH3
CH3
Cl Cl
Ans. (A)

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5. In the following acid-base reaction, in which can backward reaction is favoured?

(A) EtO– + OH (B) KH + EtOH

–
O

(C) Me3CO–+ H2O (D) + CH3OH

Ans. (D)

6. Among the xylenes, which is thermodynamically most stable ?

(A) (B) (C) (D) All are equally stable

Ans. (B)

7. In sets a – d, only one of the set is incorrect regarding basic strength. Select it :

NH2

(A) Ph — NH — Ph1 < Ph — NH2 < (strong base)

H
N
(B) < <
N N
H

(C) < <

N N N
H H
NH2 NH2 NH2

(D) < <

NO2 CH3

Ans. (C)

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8. Which one of the following most stable ?

H Br H Br H Br Br
H H H H H H H H
(A) (B)
+
(C) (D) H
+
H + H H H H H H H
+
:NH2 :NH2 NH2 :NH2

Ans. (C)

9. Which of the following is not an appropriate resonance structure of the others

– – –
O O O O

(A) (B) (C) (D)

O O + O O
+ +

Ans. (D)

10. Identify benzene rign which has maximum e– density :

O O O
O
O
(A) (B) (C) (D)
O
O

Ans. (A)

11. Most basic isomer of compound C3H7N :

(A) CH3–CH2–CH=NH (B) CH3–CH=CH–NH2

(C) CH2=CH–CH2–NH2 (D) CH2=CH–NH–CH3

Ans. (C)

O O
+ +
NH NH +
12.
NH
A B C
Correct acidic strength :
(A) A > B > C (B) B > A > C (C) C > A > B (D) A > C > B

Ans. (D)

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13. Which will be least stable R.S. (least contributing) :

+ – – +
(A) CH2=CH– C H– C H–NH2 (B) C H2–CH=CH–CH= N H2
– + – +
(C) C H2– C H–CH=CH–NH2 (D) CH2=CH– C H–CH= N H2

Ans. (A)

14. For the molecule

a
HO b
OH

c
OH
The acidic strength order :
(A) Hc > Hb > Ha (B) Hb > Hc > Ha (C) Ha > Hb > Hc (D) Ha > Hc > Hb
Ans. (C)
15. In which case 2nd R.S. is more stable w.r.t. Ist R.S. :
–
+ O 2+ O
(A) CH3–N CH3–N
– –
O O
+
O + O
(B) CH2

+
(C) CH3–C–OCH3 CH3–C=OCH3
O –
O
+ – – +
(D) CH3–O=CH–CH–CH=CH2 CH3O–CH–CH–CH=CH2
Ans. (B)
16. Choose compound having highest pKb value :

NH
NH2 (a)
N
NH
NH2 (b)
N
NH
H2N (c)
N
(A) a (B) b (C) c (D) Both a & b

Ans. (C)

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17. Decreasing order :

p NH q r NH

O O
of marked bond length.

(A) p > q > r (B) q > p > r (C) r > q > p (D) p > r > q

Ans. (D)

18. Which of the following cations is most stable :

+
+
+
(A) (B) (C) (D) +
CH3 CH3 CH3 CH3

Ans. (D)

19. Consider the following reaction involving two acids shown below : formic acid and HF. Which of the following

statements about this reaction are true ?

(a) Formic acid is the strongest Bronsted acid in the reaction

(b) HF is the strongest Bronsted acid in the reaction

(c) KF is the strongest Bronsted base in the reaction

(d) KO2CH is the strongest Bronsted base in the reaction

(e) The equilibrium favours the reactants

(f) The equilibrium favours the products

(g) Formic acid has a weaker conjugate base

(h) HF has a weaker conjugate base

O O
+ – – +
KF + H OH H O K + HF
pKa = 3.8 pKa = 3.2

(A) a , b and f (B) b , d and h (C) a , c and h (D) b , d , e and h

Ans. (D)

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20. Use the following data to answer the question below :

H2
Ni H = –28.6 kcal mole–1

excess H2
(Ni) H = –116.2 kcal mole–1

Anthracene
Calculate the resonance energy of anthracene :

(A) 84 kcal / mol (B) 100 kcal / mol (C) 110 kcal / mol (D) 116 kcal / mol

Ans. (A)

21. Which is the major product of the following reaction ?

H
N
HCl Product
N H 1 mole
–
Cl H
H + H N
N H
(A) (B)
N+ Cl
–
N H H

Cl H H
N N Cl
(C) (D)
N H N H
Ans. (B)
22. Rank the following substance in order of decreasing heat of combustion (maximum  minimum) :

CH3 CH3 CH3

1 2 CH3 CH3
3 4
(A) 1 > 2 > 3 > 4 (B) 3 > 4 > 2 > 1 (C) 2 > 4 > 1 > 3 (D) 1 > 3 > 2 > 4

Ans. (C)

23. Which statement about the following equilirium is true ?

– + + –
O K + H2O OH + KOH
pKa = 15.7
t-butoxide pKa = 18

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(A) The equilibrium favours the product

(B) t-Butoxide is the dominant aionic species in the equilibrium

(C) Water is the weaker acid

(D) t-Butoxide is stabilized by resonance

Ans. (A)

24. For the following two acid base reactions, which statement is true ?
– –
(I) CH3CH2 + CH3NH2 CH3CH3 + CH3NH
pKa = 35 pKa = 50
– –
(II) F + H2O HF + HO
pKa = 15.7 pKa = 3.2
(A) It is favoured to the right, II is favoured to the left
(B) It is favoured to the lest, II is favoured to the right
(C) It is favoured to the right, II is favoured to the right
(D) It is favoured to the lest, II is favoured to the left
Ans. (A)

COOH HO
(Q)
25.

HO COOH HO COOH
(P) (R)

The correct acidic strength of acidic hydrogen P, Q and R is respectively :

(A) P > Q > R (B) P > R > Q (C) R > Q > P (D) Q > R > P
Ans. (A)

26. Compare relative stability of following resonating structure ?

– O O
O
–
(p) (q) (r)
CH3
C C C
N N N–

(A) p > q > r (B) q > p > r (C) q > r > p (D) p > r > q

Ans. (D)
27. The heat of hydrogenation of 1-hexene is 126 kJ mol. When a second double bond in introduced in the molecule, the heat of
hydrogenation of the resulting compound is found to be 230 kJ mol–1. The resulting compound (diene) is :
(A) 1,5-hexadiane (B) 1,4-hexadiane
(C) 1,3-hexadiane (D) Cannot predict from the given information
Ans. (C)

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28. Among the following compounds, the most basic compound is :

(A) (B) (C) (D)

N N O N
H H
Ans. (D)

29. Decreasing order of acidic strengths of following compounds is :

H CN

(x) (y) (z)

(A) x > y > z (B) y > x > z (C) z > y > x (D) z > x > y
Ans. (D)

H
(X)
N NH (Y)
30.
(Z)
O N O
H
The correct basicity order of atoms X, Y and Z is :

(A) X > Y > Z (B) Z > Y > X (C) Z > X > Y (D) Y > X > Z

Ans. (D)

31. Maximum number of Na metal equivalent used will be ?

OH

Na
HOOC C CH=CH2 (x eq.)

(A) 1 (B) 2 (C) 3 (D) 4

Ans. (C)

32. HO2C–CH=CH–OH, the direction of electron movement would be :

(A) toward –OH group

(B) neither –OH nor towards –CO2H

(C) toward –CO2H group

(D) At low temperature –OH group and at high temperature toward –CO2H group

Ans. (C)

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33. Polarisation of electron in acrolein (CH2-CH–CH=O) or R.H. can be written as :

+ – – +
(A) CH2 CH CH O (B) CH2 CH CH O

– – + +
(C) CH2 CH CH O (D) CH2 CH CH O
Ans. (A)

34. Consider following three halides :

(I) CH3–CH2–Cl (II) CH2=CH–Cl (III) C6H5Cl

Arrange C–Cl bond length of those compounds in decreasing order :

(A) I > II > III (B) I > III > II (C) III > II > I (D) II > III > I

Ans (A)

35. Gas liberated during reaction

COOH

NaHCO3

SO3H
14
(A) CO2 (B) SO2 (C) CO2 (D) SO3

Ans. (A)

36. Compound which is soluble in NaOH & NaHCO3 both :

OH OH CH3 OH
NO2
(A) (B) (C) (D)

NO2

Ans. (B)

37. Acidic strength order of given compound :

OH COOH OH COOH

NO2 CH3 (III) (IV)

(I) (II)

(A) I > IV > III > II (B) I > IV > II > III (C) IV > II > I > III (D) IV > I > II > III

Ans. (C)

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38. Which of the following is the correct order of basic nature.

(P) (Q) (R)

N N
N N
H
(A) Q > R > P (B) R > Q > P (C) R > P > Q (D) Q > P > R

Ans. (B)
39. Among the following compounds, the most acidic is :
(A) p-nitrophenol (B) p-hydroxybenzoic acid
(C) o-hydroxybenzoic acid (D) p-toluic acid

Ans. (C)

40. Decide decreasing order of bond length of C–Cl bond x,y and z in the following structure :
Cl
y
Cl
z

Cl x
(A) x > y > z (B) y > z > x (C) z > x > y (D) y > x > z
Ans. (D)
41. Imidaole has pKa = 7 with respect to its conjugate acid. Which N is protonated in this conjugate acid and why ?
3
N
Imidazole
1
N
H
(A) N1 becuase imidazole is an aromatic heterocycle where n = 1 as per Huckel’s rule.
(B) N1 is protonated because it is sp3 hybridised
(C) N3 is protonated because it is sp2 hybridised and has localised lone pair
(D) N1 is protonated because the lone pair is part of the aromatic pi system
Ans. (C)

42. In each of the following pairs of ions, which ion is more stable ?
+ + + +
(a) C6H5–CH2 and CH 2=CH–CH2 (b) CH3–CH2 and CH 2=CH
(I) (II) (I) (II)

+ +
CH2 CH2 CH3–CH–CH3 CH 3–N–CH3
(c) and (d) and
CH3–C–CH3 CH 3–C–CH3
+ +
(I) (II) (II)
(I)
(A) a–I , b–I , c–II , d–II (B) a–II , b–II , c–II , d–II

(C) a–I , b–I , c–I , d–I (D) a–II , b–II , c–I , d–I

Ans. (A)

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43. Which of the following two carbonium ions is more stable ? Explain why.

:
NH2
(a) + + (b) + +

(I) (II) (I) (I)

(A) a–II , b–II (B) a–I , b–I (C) a–I , b–II (D) a–II , b–I
Ans. (A)
44. Which of the most stable arenium carbocation ?
CH3 CH3 CH3 CH3
NO2
+
(A) H (B) (C) (D) H
+ +
+ NO
H NO2 H NO2 2

Ans. (C)
45. Which of the following compounds are aromatic compounds ?
H H
N N O S
(I) (II) (III) (IV)
N

H
O S N
N
(V) (VI) (VII) (VIII)
N N
N H
H H O OH
N N N
(IX) (X) (XI) (XII)
N N
O OH
(A) I , II , III , IV , V , VI , VIII , X , XII (B) I , II , III , VI , VIII , X , XI , XII

(C) I , II , III , IV , V , VI , VII , X, XII (D) I , II , III , V , VII , VIII , IX , X , XII

Ans. (C)

46. A compound shows a large dipole moment. Which of the following resonance structures can be

used to adequately explain this observation ?

–
+ – – +
(i) (ii) (iii) (iv)
+
(A) i (B) iii and iv (C) ii and iii (D) iv only

Ans. (B)

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47. Which of the following is not a resonance structure of the others ?

–
O O O O
– –
(A) (B) (C) (D)
–

Ans. (D)

48. Identify correct acidic strength order in the following compounds :

(i)
HO O

(ii) (iii)
HO OH

(A) ii > i > iii (B) ii > iii > i (C) i > iii > ii (D) iii > i > ii

Ans. (A)

49. The acidity of the protons H in each of the following is :

+ +
NMe3 PMe3 CH3
H H H

(i) (ii) (iii)

(A) i > ii > iii (B) ii > iii > i (C) ii > i > iii (D) iii > i > ii

Ans. (C)

50. Identify correct acidic strength order in the following compounds :

H H H

(i) (ii) (iii)

(A) iii > ii > i (B) ii > iii > i (C) i > iii > ii (D) iii > i > ii

Ans. (A)

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51. Identify correct stability order in the following compounds :

+ + +
C CH CH
OO O O O O
(i) (ii) (iii)

(A) i > ii > iii (B) ii > iii > i (C) i > iii > ii (D) iii > i > ii

Ans. (B)

52. Which nitrogen in LSD is most basic ?

O
(3)
(1)
C–N(C2H5)2
HN
(2)
N
CH3

(A) 1 (B) 2 (C) 3 (D) All are equally basic

Ans. (B)

53. The decreasing order of basic strength is :

(5)
H2N (4)
NH
:

(1) N (3)
:N
:

H2N N (2)
CH3

(A) 1 > 5 > 3 > 4 > 2 (B) 4 > 1 > 5 > 3 > 2 (C) 5 > 4 > 1 > 2 > 3 (D) 4 > 5 > 3 > 1 > 2

Ans. (B)

54. Which of the following acid gives evolution of CO2 with NaHCO3 ?

OH HO O
NO2 COOH
(I) HCl (II) (III) (IV)
COOH
HO O
NO2

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COOH

(V)

COOH

(A) I , III , IV , V (B) III , IV , V (C) I , II , III , IV , V (D) I , III , IV

Ans. (C)

55. Maximum resonance energy is known for :

(A) (B) (C) (D)

Ans. (D)
56. Which of the following is most basic ?

N N
N N N
N N
(A) (B) (C) (D)
N

Ans. (C)
57. Which of the following is the most stabilised carbocation ?

OMe OMe OMe OMe

+
(A) (B) (C) + (D) +
+

Ans. (D)

58. The most stable canonical structure of the given molecule is :

–
– –
O O+ O + O
– +
(A) (B) (C) (D)

Ans. (B)

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59. Which is the least likely protonation site in the conjugated alkene shown below ?

(c)

(d) (a)

(b)

(A) a (B) b (C) c (D) d

Ans. (C)

60. Choose those that are resonance structures of protonated methyl vinyl ketone :

+ H
H :O
C C
H C CH3
H
Protonated methyl
vinyl ketone

H H H
:

:
:

H :O H :O H :O
+C C
(1) C C (2) (3) C + CH
H C + CH3 H C CH3 H C CH3
H H H

(A) 1 (B) 2 (C) 3 (D) 1 & 2

Ans. (D)
61. Which one of the following is the most basic compound :
(A) C6H5 – NH2 (B) C6H5 – NHCH3 (C) C6H5–N(CH3)2 (D) C6H5N(C2H5)2
Ans. (D)
62. Which of the following resonating structure is not possible for 2, 4, 6-trinitroiodo benzene

 
I  I I
I
O2N NO2 + O O2N NO2 O2N NO2
O2N N
O

  
N N N
NO2
O O O O O O
(I) (II) (III) (IV)

(A) I (B) II (C) III (D) IV

Ans. (B)

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63. Consider the following compound

O OH

OH O
CH3 –C–COOH
COOH III
O OH II
I
Which of the above compounds reacts with NaHCO3 giving CO2

(A) I, II and III (B) I and III (C) II and III (D) I and II

Ans. (A)

64. Which of the following is most acidic :

COOH COOH
COOH COOH

(A) (B) (C) (D)

CH3 NO2 CH3

Ans. (B)

65. Arrange marked atom in decreasing order of acidic strength

2
H O
3 1
H N H

(A) 1 > 2 > 3 (B) 3 > 2 > 1 (C) 2 > 1 > 3 (D) 2 > 3 > 1
Ans. (C)

66. Correct decreasing order of basic strength -

NH2
NH2 NMe2
N
N H N N
N H N
H
(II) (III)
(I)

(A) III > II > I (B) II > I > III (C) I > II > III (D) III > I > II

Ans. (A)

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67. Basicity order of N in following compound is :

O CH3 b CH3
N
H 2N C CH2 CH2 NH C CH3
c
NH
a

CH3 N
d
CH3

(A) b > d > a > c (B) a > b > d > c (C) a > b > c > d (D) a > c > b > d
Ans. (B)
68. Which of the following is the correct order of acidic strength.

COOH OH OH
NO2
(A) > > H2CO3 >

NO2

COOH OH OH
NO2
(B) > > > H2CO3

NO2

COOH OH OH
NO2
(C) > H2CO3 > >

NO2

(D) None

Ans. (A)

1 1 1
2 2 2
69. 3 3 3
4 4 4

These are three canonical structures of naphthalene. Examine them and find correct statement among the following:
(A) All C–C bonds are of same length (B) C1–C2 bond is shorter than C2–C3 bond
(C) C1–C2 bond is longer than C2–C3 bond (D) None
Ans. (B)

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NMe2 NH2 SO3H NO2 Br

70.

A B C D E

Steric inhibition of resonance takes place :

(A) In A, B only (B) In A, B, C, E (C) C only (D) In A only
Ans. (D)
71. Consider the following two structures and choose the correct statements -

O +
O O O
+
N N

(I) (II)

(A) Carbon-nitrogen bond length structure I is greater than that in structure II

(B) Carbon-nitrogen bond length structure I is less than in structure II
(C) Carbon-nitrogen bond length in both structure is same.
(D) It can not be compared.
Ans. (B)
72. Which of the following statements would be true about this compound :

NO2
5

1 3
NO2 NO2
Br

(A) All three C–N bonds are of same length.

(B) Cl–N and C3–N bonds are same length but shorter than C5-N bond.
(C) Cl–N and C3–N bonds are same length but longer than C5-N bond.
(D) Cl–N and C3–N bonds are of different length but are longer than C5-N bond.
Ans. (C)
73. Cyclopentadienyl anion is much more stable than allyl anion because
(A) Cyclic anion is more stabel than acyclic anion
(B) Delocalised anion is more stable than localised anion
(C) Cyclopentadienyl anion is aromatic in nature
(D) None of these
Ans. (C)

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74. Examine the following two structures for pyrrole and choose the correct statement given below
+

N N
H H
(I) (II)
(A) II is not an acceptable resonating structure because carbonium ions is less able than nitride ion.
(B) II is not an acceptable resonating structure because there is charge separation.
(C) II is not an acceptable resonating structure because nitrogen has ten valance electrons
(D) II is an acceptable resonating structure
Ans. (C)

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MULTIPLE CHOICE EXERCISE

1. Which of the following represents R.S. of biphenyl ?

+
(A) (B) – +

(C) (D)

Ans. (B,C,D)

2. What is the correct resonance hybrid of following molecules ?

+ + + –
(A) H2N C NH2 (Urea) (B) CH2 CH C CH (Vinyl acetylene)

O
–
–
O + –
(C) CH3—N (Nitro methane) (D) CH2 CH Cl (Vinyl chloride)
–
O
Ans. (A,B)

3. Which of the following option is incorrect ?

(A) PhN2+ is more stable w.r.t. RN2+ because in PhN2+ +ve charge undergoes delocalisation in ring
– –
CH2 CH2

(B) is more stable than

F Cl
(C) In PhSO3H, m position is relatively highly e– dense w.r.t. o/p position
(D) The e– movement with following compound HO–CH=CH–CO2H is towards –CO2H group
Ans. (A,B)
–
O O
4. Dianion of squaric acid

O O–
(A) 4-identical resonating structure (B) C–C bond lengths are identical
(C) C–O bond length = C–C bond length (D) Antiaromatic in nature
Ans. (A,B)

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5. Circle represent most acidic hydrogens in these molecules. Which of the following is correct representation

OH O
O
MeO2C
OH SH
(A) (B) (C) (D) None of these
HO
CF3 CO2H F

Ans. (A,B,C)

6. In the following acid base reaction, in which can forward reaction if favoured ?

–
(A) EtO + OH (B) KH + EtOH

O–

(C) – (D)
Me3CO + H2O + CH3OH

Ans. (A,B,C)

7. Which of the following is/are planar molecule ?

(A) H2C = C = CH2 (B) H2C=C=C=CH2 (C) H2C=C=O (D) NC–HC=CH–CN
Ans. (B,C,D)

8. Select the correct option(s) among the following :

(A) Correct acidity order is CF3–CH2–OH > CCl3–CH2–OH > CH3–CH2–OH

(B) Correct basicity order is CH3–CH2–NH2 > CH3–CH=NH > CH3–CN

(C) Correct acidity order is CH3–CH–CH2–OH > CH3–CH–CH2–OH > CH3–CH–CH2–OH

Me NO2 + NMe3

(D) Correct acidity order is HCCH > CH2=CH2 > CH3–CH3

Ans. (A,B,D)

SO3Na

9. Which will give HaOOC–CH2 C ONa as a product ? (Assume that ions were not present in

ONa

reactant)

(A) NaNH2 (B) Na (C) NaHCO3 (D) NaH

Ans. (A,B,D)

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10. Correct statement(s) is/are regarding given compound :

N N

N N
(I) H (II) (III) H
(A) Basic strength order I > II > III

(B) Acidic strength order I > II > III

(C) III compound having all inductive, mesomeric & hyperconjugation effects

(D) All I , II and III are heterocyclic compounds

Ans. (A,B,C,D)

11. Which of the following option(s) has correct direction of dipole moment ?

(A) (B) (C) CH–CH3 (D)

Ans. (B,C,D)

12. Identify the binary mixture(s) that can not be separated into the individual compounds, by differential extraction,

as shown in the given scheme :

NaOH (aq.)
Compoud-1 + Compoud-2
Binary mixture containing
compound 1 and compound 2
NaHCO3(aq.)
Compoud-2 + Compoud-2

OH OH CH2–OH OH
O2N NO2
(A) , (B) ,

NO2 SO3H

OH CH2–OH OH CH2–OH
NO2
(C) , (D) ,

COOH
Ans. (A,B,C)

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13. In which of the following compound(s) hyperconjugation effect is present :

(A) (B) (C) CH3–CH=CH3 (D)

CH2

Ans. (B,C,D)

14. Hydrogen bonding is primarily responsible for which of the following observation :

(A) p-nitrophenol is more acidic than o-nitrophenol

(B) Dimethyl amine is more basic than trimethyl amine in aqueous medium

(C) Boiling point of salicyladehyde is less than p-hydroxy benzaldehyde

(D) Benzoic acid is more acidic than phenol

Ans. (A,B,C)

15. In which of the following reaction product is/are aromatic ?

OH Br
+
H Ph–Li AgNO3
(A) (B) (C) (D) None of these

Ans. (A,B,C)

16. Select the incorrect statement(s) :

NH2 NH2
CH3
(A) is more basic than

COOH COOH
CH3
(B) is less acidic than

NMe2 NMe2
CH3
(C) is more basic than

NO2 NO2
CH3
(D) has shorter C–N bond length than

Ans. (A,B,D)

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17. Correct order of bond length of (C—O) bond :

H
O O O–H
p s
u
t
–O q r
O
O
(A) s > p > t (B) u > q > r (C) p = q (D) p > t > r

Ans. (A,B,C,D)

O
18. Compound(s) having higher bond rotation energy barrier across C = C than compound is/are :
O
O
O
(A)
O O (B)

O
O
(C) (D) O
O
Ans. (A,B,C,D)

19. Which of the following options are correct :

(A) p-chloro phenol is more acidic than p-fluoro phenol

–
O O
(B) Squaric acid dianion have identical R.S.

O O–
(C) Squaric acid dianion have all C–O bonds identical

(D) Squaric acid dianion have all C–C bond identical

Ans. (A,B,C,D)

20. Incorrect stability order is/are :

O + +
(A) O > + (B) >
+
O
+
(C) > (D) >
+
+ N + N
H H
Ans. (B,C)

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21. Which of the following is / are aromatic species :

(A) N (B) + (C) (D)

H O

Ans. (A,B,C)

22. Which of the following are incorrect :

(A) Order of heat of hydrogenation C–C=C–C–C–C=C–C < C–C–C=C–C=C–C–C

(B) Order of heat of combustion > > >

+
+
(C) Order of stability of carbocation > >
N +
N
H

(D) Order of heat of combustion is >

Ans. (A,B,C, D)
23. Select true statement(s) :

(A) Resonance effects bond length

(B) Inductive effect is a permanent effect.

O
COH
(C) In H2C most acidic H is connected directly to oxygen not on carbon.
COH
O
(D) In urea both C–N bond length are identical

Ans. (A,B,C,D)

24. Which has non-zero dipole moment ?

(A) (B)

(C) (D) HO OH

Ans. (A,B,C,D)

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25. Identify the correct order of dipole moment :

O O O
O
>
(A) > Ph Ph (B)
Ph Ph

(C) < (D) >

Ans. (A,B,D)

26. From the compound shown below, choose which is aromatic :

+ – –
O
(A) (B) (C) (D)
B
H
Ans. (A,B,C,D)
27. Identify the feasible reactions

COOH COONa

(A) + NaHCO3  + H2O + CO2

NH2 NHNa

(B) + NaHCO3  + H2O + CO2

OH ONa

(C) + NaHCO3  + H2O + CO2

COONa COOH COOH COO–

(D) +  +

NO2 NO2

Ans. (A, D)
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28. Select the number of compounds in which deprotonation gives aromatic anion :

O
HO CH2 O O
HN NH
O O
H
(A) (B) HO (C) (D)
O O
N O
Barbituric acid OH OH
Ascorbic acid H
(Vitamin - C)

Ans. (A, B, C, D)
29. Select correct statement :
(A) Carbon-oxygen bonds are equal length in acetate ion
(B) Resonating structures of acetate ion are equivalent
(C) Carbon-oxygen bonds are of unequal length in formate ion
(D) Resonating structures of formate ion are equivalent
Ans. (A, B, D)

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Single Choice Exercise

1. What is the major product of the following reaction ?

O
CH3MgI H3O
Et2O

CH3 OH
(A) (B)

CH2 OH CH2 CH3

O
CH3 OH
(C) (D)

CH3
CH3

CH3
C OCH3
PhMgBr
2. O (1 equivalent)
(P). Product (P) is :

CH2 COCH3
O

CH3 CH3O
C Ph C Ph
(A) (B)
O

CH2 COCH3 CH2 COCH3

O O

CH3 CH3
C Ph C OCH3
(C) (D)
O O

CH2 COCH3 CH2 C Ph

CH3
O O

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3. Reaction- 1 ;

SH O SH OH
CH3
HO C Cl C
CH3
1. x CH3MgBr

2. H 3O OH
CH3
C Cl C
CH3
O OH
Reaction- 2 ;

O OH
C O Et CH3 C CH3

1. y CH3MgBr

2. H3O

CH2 Cl

What is the ratio of (x/y) in above problem ?

(a) 1.5 (b) 2 (c) 2.5 (d) 3

4. In which of the following reaction 2° alcohol is obtained as a product ?

(1). CH3MgBr (1). MgCl

(A) (2). H 2O (B) O
(2). H2O

(1). CH3MgBr
(C) (D) Both (a) and (b)
(2). H2O

5. In which the following reactions product formed is same ?

(A) MeMgX (B) MgX

P P

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(C) +
MgBr P

(a) (i) and (ii) (b) (ii) and (iii) (c) (i) and (iii) (d) (i), (ii) and (iii)

6. Which of the following reaction sequences would be the best for synthesis of 2-pentanone ?
O

CH3MgI H 3O
(A) CH3 CH2 CH2 C H Et 2O

CH2 CH2 CH3MgI H3O



(B) CH3 CH O Et2O

CH3MgI H3O 
(C) CH3 CH2 CH2 C N Et 2O

O

CH3MgI H3O
(D) CH3 CH2 CH2 C H Et 2O

OH
CO2CH3 C(CH3)2
7. x CH 3MgI ; Dimethyl phthalate
+
H

CO2CH3 C(CH3)2
OH
Number of mole (x) of Grignard reagent consumed in the above reaction is :
(A) 2 (B) 3 (C) 4 (D) 5

O (1) CH 3MgBr
(excess)
8. Et O C O Et (A), Product (A) is :
(2) H 3O

O O OH

(A) CH 3 C O Et (B) CH3 C CH3 (C) CH3 C CH3 (D) CH3 CH2 CH3
CH3

O O +
9. PhMgBr + H (A), Product (A) is :
excess

O OH OH O
(A) Ph C Ph (B) Ph C Ph (C) Ph C (D) Ph C O
Ph Ph

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O
14
(i) PhMgBr
10. CH3 C O H (A)  (B)
(gas) (ii) H 3O

O
14
NaH CO3 (i) PhMgBr
CH3 S O H (C)  (D)
(gas) (ii) H3O
O
Product (B) and (D) in the above reaction are :
O O O O

(A) Ph C O H , Ph S O H (B) Ph C O H , Ph S O H
14

O
O O O O

(C) Ph C O H , Ph C O H (D) Ph C OH , Ph S O H
14 14 14

11. CH3MgBr NH4Cl Products.

diethyl ether H2O

CH3
comment on optical activity of the products. They are :
(A) racemix mixture (B) diastereomers
(C) meso forms (D) optically inactive due to absence of chiral centre
OH H OH H
Ph Ph
MeO2C N N
tBu (1) xPhMgBr HO tBu
12. (2) H 3O


HO HO
Number of equivalents of Grignard reagent (x) used in reaction (1) is :
(A) 3 equivalent (B) 4 equivalent (C) 5 equivalent (D) 6 equivalent

OH
Br CH Ph
13. (1) Mg : ether
(2) Ph–CHO
3 
(3) H O
N N
H H
The given product can not be obtained in the above reaction, Identify the correct product obtained .

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(A) (B)

N CH Ph N
H OH CH Ph
OH

OH O

CH Ph CH Ph
(C) (D)

N N

O
Me H
MeMgBr
14. Product of the reaction is :

Ph
H

Me Me
Me H Me H
(A) (B)

HO H H OH
Ph Ph
(C) Both (a) and (b) (D) None of these

(i) MeMgI H+
15 (A) (B) Major
(ii) NH4Cl 

CH2

(A) (B)

(C) (D)

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(i) THF
16.  MgBrCH 2 CH 2 CH 2 CH 2 MgBr (ii) H 3O+
product; product of the reaction is :

O O

O
(A) HO   CH 2 3  C CH 2  CH 2  CH3 (B)

HO (CH2)3 OH

(C) HO (D)
CH CH2 CH3
HO CH2 CH2 CH3
OH

O OH
C Cl C CH3
(i) x CH3MgBr CH3
17. +
(ii) H

C Cl C
OH
Me
O Me
Number of moles of CH3MgBr consumed in above reaction is :
(A) 2 (B) 4 (C) 6 (D) 8
18. End product of the given reaction is :
Cl
Mg 1. CH2O
Et 2O
(A) (B)
2. H3O

OH
OH
(A) (B)

OH
(C) (D)

19. Which of the following reaction sequences would be the best for synthesis of t-butyl alcohol ?
O
Et 2O H 3O CO2 H 3O
(A) CH3CH2MgBr + CH2 CH2 (B) CH3CH2CH2MgBr Et2O

O O

(C) CH3MgBr + CH3 C CH3 Et2O H 3O (D) CH3CH2MgBr + CH3 Et2O H 3O
C H

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20. What is the major product of the following reaction ?

H 3O
CH3 C N Et 2O

H
N
(A) CH3–CH2–NH–CH3 (B) CH3 C CH3
O O

(C) CH3 C CH3 (D) CH3 CH2 C OH

21. CH 3CO 2 Et   CH 2 5  MgBr 2 
(2) H 
 C7 H14 O ; compound (A) will be :
( A)

OH
OH
OH O

(A) (B) (C) CH3 C (CH2)4 CH3 (D)

O
(1) excess CH3–Li
22. PhMgBr  CH 3  CN 
H O
(A) Ph C O H (2) H 3O
(A)
3

Same product (A) will form in both reactions . A is :

OH
(A) Ph C CH3 (B) Ph CHO

CH3
O
(C) Ph C CH3 (D) Ph CH2 CO2H

23. What is the product (B) of the following reaction sequence ?

Br
Mg
Et2O
A

O
(1) Et2O
B
A+ CH3 (2) H 3O


OH

OH CH3
(A) (B)
CH3

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O OH

CH3
CH3
(C) (D)
OH
OH

CH2 OH

CH OH + CH3MgBr xCH4
24. (Excess)
CH2 SH
What is the value of x in the above reaction ?
(A) 1 (B) 2 (C) 3 (D) 4
25. 0.40 g of an organic compound (A), (M. F. - C5H8O) reacts with x mole of CH3 MgBr to liberate 224 mL of a gas at
STP. With excess of H2, (A) given pentan -1-ol. The correct structure of (A) is :
(A) CH3– C C –CH2–CH2–OH (B) CH 3  CH 2 – C C –CH2–OH
(C) H– C C CH 2  CH 2  CH 2  OH (D) H– C C –CH2– CH CH3

OH
O

Br2 Mg CH3 C CH3 H

+

26. CH3  CH  CH 2 h Dry ether 

(X)
(low conc.) NH4Cl (major)

End product (X) of the above reaction is :

CH2

(A) CH 2  CH  CH 2  C CH3 (B) H 2 C  CH  CH  C CH3

OH CH3
(C) H 2 C  CH  CH 2  C CH3 (D) H 2 C  CH  CH 2  CH  CH2 OH

CH3 CH3
27. In the given reaction

[X] will be :

(A) (B) (C) (D)

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28. Which will give silver mirror test with Tollens reagent :
(A) C6H5CHO (B) CH3–CHO (C) HCOOH (D) All of these

29. ; A is :

(A) (B)

(C) (D)

30. Major product is :

COOH

(A) (B) (C) (D)

31. Which of the following can be oxidised by MnO2 :

(A) (B)

(C) (D)

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32. A ; A is :

COOH OH

(A) (B)

O O

(C) (D)
O

O O

33. Phthalic Anhydride : A is :

Me Me

(A) (B)

Me

Me

Me
(C) (D)

Me
Me

SH
HS H2/Ni
34. O

The end product of the reaction are :

(A) SH and SH (B) S CH2 CH2 SH

S SH
(C) and H2O (D) and HS
S

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CH2
35. H2,Pd

CH3
Products of the above reaction will be :
(A) Racemic mixture (B) Diasteromers
(C) Meso (D) Structural isomer

D
NH2-NH 2
36. H 2O 2
Product :

(A) ` (B) H

D
H

(C) H (D) Both (B) and (C)

H
D

H3C D
H2/Ni
C C
37.
D CH3
Product of above reaction will be :
(A) Racemic mixture ` (B) Diastereomers
(C) Meso (D) Constitutional isomers

O O

38. C C

Which reagent will be used for the above conversion ?

(A) Na/Liq. NH3 (B) H2, Pd–CaCO3
(C) Li, Ph–NH2 (D) H2, Pt

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COOH

Li
39. Liq. NH 3
Major product :

COOH COOH COOH CH2OH

(A) (B) (C) (D)

OCH3

Na, Liq, NH3

40. Major product :

OCH3 OCH3

(A) (B)

OCH3

(C) (D) None of these

41. If the following compound is treated with Pd in excess of H2 gas, how many stereoisomers of the product will be
obtained ?

(A) 1 (B) 2 (C) 3 (D) 4

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O O
NaBH4
42. Product

O Cl
O
The product is :

(A) HO OH (B) CH3–CH3–OH

OH

O
OH O
O
(C) HO OH (D)
O OH
OH

AgCN H2, Ni
43. Br A B

The final product (B) is :

NH2
(A) (B) N
H
H
(C) N (D) NH2

44. In organic layer test, CS2 or CCl4 is added to Lassaigne’s extract and then Cl2 water or KMnO4 is added. This test is
used to distinguish between
(A) Br and I (B) Cl and Br
(C) Cl and I (D) Cl , Br and I
45. Which alkyne gives 3-ethylhexane on catalytic hydrogenation ?

(A) (B) (C) (D) All of these

7

46. Number of moles CrO3 required to oxidise completely 9 moles of 2-heptanol to the corresponding ketone ?
(A) 5 (B) 6 (C) 4 (D) None

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47. In compound A(C30H60O) following tests are observed negatively, A can be

Br2/H2O
-Ve
Tollen's reagent
C30 H60 O -Ve
(A) Na metal -Ve

(A) An unsaturated ether (B) An epoxide (C) A cycloalkanol (D) Can’t predict
48. A set of reagents (1 to 7) are successively reacted with the following compound

O O
HO
OH
OH

CH

1. NaHCO3 2. 2,4, DNP 3. Na metal 4. AgNO3 + NH4OH 5. Fehling’s solution

6. Cu2Cl2 + NH4OH 7. Br2/H2O
The reagent which give positive test with the given compound are :
(A) 1, 2, 3, 4, 5 (B) 3, 4, 5, 6, 7 (C) 1, 2, 3, 4, 7 (D) 1, 2, 3, 4, 6, 7
49. Give the correct order of initials T or F for following statements. Use T if statement is true and F if it is false.
X (molecular formula, C7H6O2) is an aromatic white solid which liberates colourless. odourless gas on reacting with
S1 : Only three of the five functional isomers of X (including ‘X’ itself) will give positive 2, 4-DNP test.
S2 : The liberated colourless, odourless gas will containing radioactive 14C.
14
S3 : Except ‘X’, no other functional isomer will liberate colourless odourless gas with NaH C O3 .

S4 : The DU of higher homolog of ‘X’ will be four.

(A) TTTF (B) FTTF (C) FTTT (D) TTFF
50. The reaction among following produces meso-compound

Me H Me H

(A) KMnO4 /OH /H 2O(cold)

  (B) KMnO4 /OH /H 2O(cold)
 
Me H H Et

Me H Me H

KMnO 4 /OH /H 2O(cold)

(C) KMnO4 /OH /H 2O(cold)
  (D)  

Et H H Me

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Multiple Choice Exercise

1. Silver mirror test with Tollens reagents is given by :
(A) C6H5CHO (B) Ph–NH–OH
(C) C 6H5 CH2 C CH2OH (D) CH3CHO

2. Fehling solution gives red precipitate with :

(A) Aromatic aldehyde (B) Aliphatic aldehyde
(C) Ketones (D)

3. Which of the following compound will give positive Tollens test

(A) CH3CHO (B)

(C) (D)

4. Which will give the Tollen test.

(A) (B)

CH2OH
O OH
O
HO H
(C) R C CH2 (D) H
H HO
H OH
OH H

O
5. CH3 C can be obtained as one of the product in reaction -
OH

O – O
(i) I2/OH CH3CO3H
(A) CH3 C + (B) CH3 C
CH3 (ii) H H

O
CH3CO3H O3
(C) C (D) CH3 CH CH2
H2O
H

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6. Following conversion can be carried out by using sequence

O O
CH3 CH2 C CH3 CH2 C
OH H

(A) (i) SOCl2 (ii) H2, Pd/ BaSO4 (B) (i) R’–OH/H+ (ii) DI-BAL H
(C) (i) Ca(OH)2 (ii) (HCOO)2 Ca/Dry distillation (D) (i) LiAlH4 (ii) Cu/300°C
7. With reference the scheme given, which of the given statement(s) about T, U, V & W is/ are correct
O
C
O LiAlH4 excess
T U W
(CH3CO)2O
+
 CrO3/H

V
(1) “T” is soluble in hot aq NaOH (2) “U” is optically active
(3) Molecular formula of W is C10H18O4 (4) V gives effervescence with aq NaHCO3
8. Compound ‘X’ (C8H8) rapidly decolourises cold aqueous KMnO4 solution. It reacts with Br2/CCl4 to yield C8H8Br8.
The structure of ‘X’ cannot be

(A) (B) (C) (D)

9. Which of the following halides does not form G.R. when treated with magnesium in the presence of ether ?
(A) Br (B) HO
H Br

(C) O2N Br (D) HOOC Br

10. Hexan-3-one can be obtained by the reaction of EtMgBr and

(A) Butanamide (B) Propanamide (C) Butane nitrile (D) Propane nitrile
11. Consider the following reactions :

(A) COOH B and  (C)

COOH
(I) (II) (III) (IV)

Which of the following group(s) of reagents is/are used in the above conversion ?
(A) (A)  Acidic KMnO4 , (B)  Ca(OH)2 , (C)  Zn-Hg/HCl
(B) (A)  O3/Ph3P, (B)  Ba(OH)2 , (C)  LAH/ether


(C) (A)  O3/H2O , (B)  Sr(OH)2 , (C)  NH 2 NH 2 O H

(D) (A)  O3/Ag2O, (B)  Ba(OH)2 , (C)  HI + Red P

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12. Select the correct Baeyer-Villiger oxidation reaction :

(A) H2SO4
  Caprolactone

O
Me Me O Ph
(B) Me PhCO3H
Ph   Me
Me Me O

O O
Me Me
PhCO 3H Ph
(C) Me Ph 
 Me O
Me Me

O O
PhCO3 H Ph
(D) Ph H  
H O
13. Select the correct group(s) of reagent(s) used in the following conversions:

Me COOH
Me Me
II
Reagent
 ,  
I
Me COOH
NO2 NO2

Me COOH Me COOH
Cl Cl OH OH
III , IV
 

(A) I  dil. HNO3 , II  Na2Cr2O7/H2SO4, III  KMnO4/NaOH, IV  PbO4/OH–, H3O

(B) I  dil. HNO3 , II  KMnO4/H, III  KMnO4/NaOH, IV  TsCl + acidic KMnO4 + H2O
(C) I  KMnO4/NaOH, II  Na2Cr2O7/H, III  KMnO4/OH–, IV  dil. HNO3
(D) I  CrO3/MeCOOH, II  KMnO4/OH–, III  KMnO4/H, IV  dil. HNO3
14. Which of the following reactions is/are correct ?

(A) Me Me 
3CrO
 Me COOH + HOOC Me
CH COOH
3

(Jones reagent)
H2CrO4 MnO2
+
Me OH No
Aq. acetone reaction
(B) H

Me OH

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SeO 2/CH 3COOH

(C) Me CH CH C CH3 CH2 CH CH C CHO
O OH O

NO2 NH2
NO2
HOOC
Oxid. Sn + HCl
B A B A B
(D)
HOOC COOH
Acidic
A KMnO4
[O]
COOH

15. Which of the following reaction(s) is/are wrong ?

Me COOH COOH
Me
Br COOH
Br 1.Mg/ether
1.Mg/ether
  

2.CO2 /H3O
(A) 2.H O (B)
3
 3.KMnO4 /H
3.KMnO4 /H 4.

Me CHO Me
CHO

1.CrO2Cl2 /CCl4
  1.CrO3  (MeCO )2 O
 
(C) 2.H2 O (D) 2.H O/OH 
2

16. Which of the following reactions is/are correct ?

SH (i) BF3
(A) O+ + C2H6 + NiS
SH (ii) Raney Ni + H2

SH
(i) BF 3
(B) CHO + Me + C3H8 + NiS
(ii) Raney Ni + H2
SH

O
O NO2
(C) Ph NO2 
PhCO H /H O 
 Ph
3 3

O O

(D) Ph Me   Ph O Me
HCO3 H/ H 3O

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17. Which of the following methods can be used to prepare propanic acid ?

Me
Me (i )Ca (OI) 2
 
(A) (ii)H O 
3
O
High pressure
(B) CH 2  CH 2  CO  H 2O 
570 670K

(Steam)

(C) Reaction of EtMgBr with dry ice followed by the acidification with dil. HCl.
(D) Sodium ethoxide is heated with CO under pressure followed by the acidification with dil. HCl.
18. Which of the following compounds reacts with NaCNBH3 ?

(A) Me – CH = NH (B) Me2C=N–Me (C) CH2OH (D) PhNO2


19. Acetonitrile (MeN C) on reaction with Cl2 with DMSO gives methyl isocyanate (MeN=C=O). Isocyanides can
also be oxidised to alkyl isocyanates with :
(A) HgO (B) Hg2O (C) Ag2O (D) O3

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Misc. Exercise
Subjective Type Questions

H /KMnO4
1. (i) (ii) CH3 CH CH2

H/KMnO4 H/KMnO4
(iii) (iv)

 
H /KMnO4 H /KMnO4
(v) (vi)

H/KMnO4 H/KMnO4,
(vii) (viii)
CO2-

 
H /KMnO 4 H /KMnO 4
(ix)  (x) 


H /KMnO4
(xi)


H /KMnO 4
(xii) C10H10  HOOC C C C COOH
C COOH

2. A to F alkenes with minimum possible carbon.

H/KMnO4
(i) A MeCOOH as the only product

H/KMnO4
(ii) B O as the only product

H/KMnO4
(iii) C MeCH2COOH as the only organic product

H/KMnO4
(iv) D

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O

H /KMnO4
(v) E HOOC–C–C–C– C C –C–C–C–COOH
O
H/KMnO4
(vi) F Acetone + Ethanoic acid
3. (i) Me CH CH CH3

(ii)

(iii) Me  CH 2  CH  CH  CH 2  CH 3

(iv)

(v) ,

(vi)

1%alkaline
A
KMnO 4
4. (i) (ii) mCPBA

+
m-CPBA/H3 O
B

Me Me
mCPBA mCPBA
(iii) (iv) C C 
Hydrolysis

hydrolysis
H H

Me
Me H Me H 1
mCPBA Ag2O or 2Ag + 2 O2
(v) C C hydrolysis (vi) C C
H Me H Ph
OH
–
KMnO4/OH , KMnO4,H 
5. (i) CH2–CH2–CH2– OH ? (ii) CH3 CH CH2 CH3 or K 2Cr2O7,H 
?

+
K2Cr2O7/H ,
or conc.HNO3, +
or conc. KMnO4/H ,

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PCC
6. (i) CH 2  CH   CH 2 3  CH 2  OH CH 2Cl 2

PCC
(ii) C6 H 5  CH  CH  CH 2  OH CH 2Cl 2

OH
PCC
(iii) CH3 CH CH2 CH2 CH2 OH CH2Cl2
(A)

OH
(iv) PCC
CH 2Cl2

CH2OH

OH
MnO2 MnO2
(v) CH 2  CH  CH 2  OH  ? (vi) CH3O CH CH2 CH2 OH Acetone

CH3O

CH3 OH
MnO2 MnO2
(vii) CH C CH C CH2 OH Acetone
? (viii) C6H5 CH CH3 CCl4 ?

HlO4 HlO4
7. (i) Me CH CH2 OH (ii) Me2C CH Et
OH OH OH
OH
HlO4
(iii) HlO4 (iv) HO CH2 CH2 CH CH2 OH
OH
OH
HlO4 HlO4
(v) CH2 CH CH2 CH3 (vi) CH2 CH CH CH3
OH OH OH OH OH
HlO4 HlO4
(vii) CH2 CH CH CH2 (viii) Me C CH Me
OH OH OH OH O OH
HlO4
(IX) Me C C Me

O O

8. How many alkene on catalytic reduction give normal butane as product.

H 2 /Pt H 2 /Pt
(i) (A)   n-butane (ii) (B)   Iso-pentane
H 2 /Pt H 2 /Pt
(iii) (C)   Neo-pentane (iv) (D)   Cyclopentane

H2
(v) (E)
Pt

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9. (a) Identify the product ?

lH 4 lH 4
LiA LiA
NaBH 4 NaBH 4
(i)  Me CHO DIB (ii)  Me2CO DIB
A A L-
L- H
H

lH 4 lH 4
LiA LiA
NaBH 4 NaBH 4
(iii)  Me COCl DIB (iv)  Me COOEt DIB
A L- A
H L-
H

(b) Identify the product ?

NaBH 4 LiAlH 4 NaBH 4 LiAlH 4
(v)  Me–COOH   (vi)  Me–COOMe  
NaBH 4 LiAlH 4 NaBH LiAlH
(vii)  Me–CONH2   (viii) 
4
Me–CONH –Me 
4

NaBH 4 NaBH 4 LiAlH4
(ix)  LiAlH 4
Me–CONMe2   (x)  CH3  CH  CH 2  

10. Give product in following reactions.

NaBH 4 LiAlH 4 NaBH 4 LiAlH4

(i)  O   (ii)  H N O  

NaBH 4 NaBH 4 LiAlH 4

(iii)  O 
4
 LiAlH (iv)   

N N
H

NaBH 4 LiAlH NaBH 4 LiAlH 4

(v)  O 
4
 (vi)  O  
O O

NaBH 4 LiAlH 4 NaBH LiAlH4

(vii)  Me CO N   (viii) 
4
CH 2  CH  CHO  

NaBH 4 LiAlH 4 NaBH 4 LiAlH4

(ix)  Ph  CH  CH  COOH   (x)   
O

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11. Give product in following reactions.

O
O

Red P + HI
(a) H (b) Red P + HI
(excess)

OH
CHO

COCH3

(c) Red P + HI
(excess)

HO CH2OH

12. Give product in following reactions.

CHO

NaBH 4 LAH
(i)   
O
COOEt

O
O
(i) LiAlH4
LAH NaOI
(ii) D 2O
(ii) C OEt 
 (A)   (B) (iii)

(iii) LiAlH4
(iv) H2O

Zn(Hg) NBS alc. HCl

O C CH3 HCl
(A) (B) (C) (D)
KOH R2O2

13. (a)

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O
O
Zn(Hg)
(b) Zn(Hg) (c) Ph C CH3 HCl
HCl ,

O O
(i) H2NNH2
(d) Zn(Hg) (e) (ii) KOH, heat
HCl , H2O

N2H4
O O KOH, heat
(excess)
Zn(Hg)
(f) HCl
(excess)
O

14. Among the following, the total number of compound which does not give Lassaigne’s test for nitrogen.

NH2

(i) (ii) H 2 N  CH 2  COOH (iii) NH 2  NH 2 (iv) Ph  N  N  Ph

O O

(v) NH2OH (vi) NH2 C NH2 (vii) Ph NH C Ph (viii) Ph – NO2

(ix) CH3CHO (x) CH3CN (xi) N

15. Amongst the following compounds the total number of compounds which gives coloured test with both Ceric
Ammonium Nitrate (CAN) and neutral FeCl3 solution.
(i) Phenol (ii) Benzyl Alcohol (iii) Benzaldehyde (iv) Aniline

(v) CH2OH (vi) (vii)

HOH2C
CH2OH
(viii) PhCH2CH(OH) CH3 (ix) Urea (x) Thiourea

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Comprehension
Paragraph for Q.16 to Q.17

Type of Addition

(a) Syn Addition (b) Anti Addition

(a) Syn Addition :- Addition of 2-groups from same side of double bond is known as Syn addition and various
products formed during reaction are
(I) Syn Addition at cis Alkene

A H A
R R
A H R
Syn addition A H A
H of A - A H A
H R
R
R
Meso

(II) Syn Addition at trans alkene

A R A
H R
A Up side R H
A A H
H Syn addition
H H A
R R
R
Threo

Optical active

R H R
H R H A
down side A
A H
Syn addition
A
R
Threo

(b) Anti Addition : Addition of 2 groups from opposite side at double bond is known as anti addition
(i) Anti addition at trans alkene

R H
R R
H A A A H
A A Anti addition
of A - A A H
H
R H
R R
Meso

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(ii) Anti addition at cis alkene

R H
R R
H A H A
A
A A A H
R
R H
R
H Threo

A R
R H A H
R H H A
A R
Threo

1% Alkaline
16. Maleic acid 
cold KMNO4
 product

COOH
COOH
COOH
HO H OH
(A) (B)
HOOC H
H OH
H OH

OH
H COOH
OH COOH
(C) OH (D) HOOC
H COOH
OH

(1)mCPBA
17. Fumeric acid 
(2)H3 O
 product

COOH COOH
COOH
COOH
HO HO H
(A) (B) H OH (C) (D) Both (A) & (C) are correct
H OH H OH
H OH COOH
H COOH

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Match The Column

18. Match the column I and II. (Matrix)
Column - I Column - II
Reactant Product
O

(A) PhMgBr  Cl  C O  Et 

H (P) Ph–CH2–OH
(excess)

(B) PhMgBr  H  C O  Et 

H (Q) Ph CH2 Ph
(excess)

OH
O OH
(C) PhMgBr  H  C  H 
H
(R) Ph C Ph
(excess)

Ph
O OH
(D) PhMgBr  CH 3  C O  Et 
H
(S) Ph C Ph
(excess )

CH3
19. Match the column I and II. (Matrix)
Column - I Column - II
Reactant Moles of PhMgBr used
O

(A) PhMgBr  Et  O  C O  Et 

H
3°alcohol (P) 1
O

(B) PhMgBr  HO  CH 2  C CH3 

H
3°alcohol (Q) 2
O

(C) PhMgBr  CH3  C CH3 

H
3°alcohol (R) 3
O

HO C Cl
(D) PhMgBr  
H
3°alcohol (S) 4

HO
20. Column - I Column - II
(Reaction) (Reagents)

H3C CH3
(A) H3C – C  C – CH3  C C (P) NaNH2/
H H

H3C H
(B) H3C – C  C – CH3  C C (Q) Alc KOH/
H CH3

(C) H3C – C  C – CH3  CH3 – CH2 – C  CH (R) H2Pd/BaSO4

(D) H3C – CH2C  CH  CH3 – C  C – CH3 (S) Na in liquid NH3
(T) Product can evolve CH4 with CH3MgBr

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21. Match the column

Column - I Column - II
(Component of mixture) (Reagent)
(A) Crystalline Na2CO3 + (P) Fehling solution
Sodium citrate + CuSO4 (aq. sol.)
(B) CuSO4 + Rochelle Salt + NaOH(Aq. sol.) (Q) Nesseler’s Reagent
(C) 10%  - naphthol in alcohol (R) Bennedict’s Reagent
(D) HgCl + KI + KOH (aq. sol.) (S) Molisch’s Reagent

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Single Choice Exercise

CH3

Br H

1. H CH3 + NaI  product ; SN2 product of the reaction is :

Acetone

CH2 CH3

CH3 CH3

I H H I
(A) (B)
H CH3 H CH3

CH2 CH3 CH2 CH3

CH3 CH3

I CH3 I H
(C) (D)
H CH3 CH3 H

CH2 CH3 CH2 CH3

Ans (B)

2. Rate of S N 2 will be negligible in :

Br Br Br Br

(A) (B) (C) (D)

Ans. (C)

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3. What is the major product obtained in the following reaction ?

CH2 Br
NH3
Product
EtOH
Br

CH2 NH2 CH2 Br CH2 NH2 CH2 NH2

(A) (B) (C) (D)
Br NH2 NH2
Ans (A)

CH3
–
4. Cl CH2 C CH2 CH2 Cl +I  
DMF
 product ; Major product of this reaction is :

CH3

CH3 CH3
(A) I CH2 C CH2 CH2 Cl (B) Cl CH2 C CH2 CH2 I
CH3 CH3

CH3 CH3
(C) H2C C CH2 CH2 Cl (D) Cl CH2 C CH2 CH2 CH2
CH3

Ans (B)

Acetone
5. H F + NaI (1 Mole)  A ; Major product of this reaction is :
(Major)
Br H

(A) H F (B) I F
I H H H

I H
(C) H (D) H
Br H Br I
Ans (B)

6. Identify products of the given reactions :

OTs
CH3CO2 Na
Product
Reaction-1 CH3CO2H
NMe2

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OTs
CH3CO2 Na
Product
Reaction-2 CH3CO2H
NMe2

O CH3
O CH3
; +Enantiomer
O
(A) O
NMe2
NMe2

O CH3

(B) O + Enantiomer ;
NMe2

O CH3

(C) O single product is obtained in both the reactions

NMe2

O CH3

(D) O single prooduct obtained in both the reactions

NMe2

Ans. (A)
(C4H8ClONa)
7. 4 - chloro -1 butanol +NaOH (A) (B)
Et2O 
Product (B) of the above reaction is :
CH3
CH2 CH3
(A) (B) (C) O (D)
O O O
Ans (B)

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Me H
KSH
8. Et D   Product ; Identify the product.

SH H
Me H Me H
(A) (B)
Et D Et D
H SH

H SH
HS Me H Me
(C) (D)
Et D Et D

H H

Ans. (D)

CH3

SO2Cl2 NBS KSH

9. (A) (B) (C) , Product (B) is
h

SH SH Br Br

(A) Br (B) Cl (C) SH (D)

Ans. (B)

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10. Product (s) formed during this reaction is / are :

*
CH OTs
CH2 2

AcONa
Product ? [C* = isotopic carbon]
AcOH

* OAc * OAc
CH2 CH2 CH2 CH2
(A) (B)

* OTs
CH2 CH2

(C) (D) Both (A) and (B)

OAc

Ans. (D)


NMe3

HO– A
11. (Major)


Major product A is :

(A) (B) (C) (D)

Ans (B)

O
Br
alc.KOH
12. Reaction (1)   (A) (major)

alc.KOH
Reaction (2)   (B)(Major)
Br

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alc.KOH
Reaction (3)   (C)(Major)

Br

Product obtained in above reactions (1), (2) & (3) is:

(A) A = B but C is different (B) A = C but B is different
(C) B=C, but A is different (D) A = B =C all product are identical
Ans. (D)

Cl
Cl Cl
3mole alc.KOH
13. Rection (1)   (A)
Cl Cl
Cl

Cl
Cl Cl
3mole alc.KOH
Reaction (2)   (B)
Cl Cl
Cl

Cl
Cl Cl

3mole alc.KOH
Reaction (3)   (C)
Cl Cl
Cl

Product obtained in above reactions (1),(2) & (3) is :

(A) A=B, C different (B) A=C,B is different
(C) B=C,A is different (D) A=B = C is same
Ans. (D)

alc.KOH
14. (x)
Br x is number of E2 product obtained
(including stereoisomers)
Find (x).
(A) 3 (B) 4 (C) 5 (D) 6
Ans (C)

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CH3
NaOEt
15. ; Major product of the reaction is :
(E2 reaction)
Cl

CH3 CH3 CH3 CH3

(A) (B) (C) (D)

Ans (B)

CH3

NaOEt
16. Cl ; Major product of the reaction is :

CH3 CH3 CH3 CH3

(A) (B) (C) (D)

Ans (A)

17. End product (D) in the given sequence is :

CH3I
CH3NHCH3 BaO (2 molar equivalent) Ag2O/ H2O
Br Br (A) (B) (C) (D)+(CH3)3 N
2 molar equivalent

O CH3

(A) (B) (C) (D)

O OH

Ans (B)
18. The following bimolecular elimination reaction (E2) is carried out with different halogen leaving groups. The per cent
yield of the two products (2- hexene and 1-hexene) for each leaving group is listed below.
X
+ CH3O– E2 +

Leaving group Conj. Acid pKa % yield of 2-hexene % yield of 1-hexene

X=I -10 81% 19%

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X=Br -9 72% 28%

X=Cl -7 67% 33%
X=F 3.2 30% 70%
Which of the following statement is (are) true concerning this series of E2 reactions ?
(A) Based on the pKa’s of the conjugate acid., I– is the best leaving group and F– is the poorest leaving group
(B) When I– , Br– Cl– are used as leaving groups, Zaitsev’s rule is followed
(C) F- is the strongest base (and therefore the poorest leaving group) and the transition state for reaction with
fluoride as the leaving group has the least double bond character
(D) a,b,c are true
Ans (D)

Ph
conc.H2SO4
19. Major product of the reaction is :

Ph OH
Ph

(A) (B)
Ph
Ph Ph Ph

(C) (D) None of these

Ph

Ans. (B)

Br
1. One eq. NaCN
(A) ; Product (A) is :
20. 2. LiAlH4

Br

Br Br

(A) (B)

CH2-NH2
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CH2NH2 CH2-NH2

(C) (D)

Br Br

Ans. (C)

Br
21. , which is not the correct statement :
(I)
(A) I is more soluble than bromocyclopropane
(B) I gives pale yellow ppt. on addition with AgNO3
(C) I is having lower dipole moment than bromocyclopropane

Br
(D) I is more ionic than
(I)
Ans. (C)
22. How many 1, 2- Shifts are involved during the course of following reaction.

OH

conc. H2SO4

(A) 1 (B) 2 (C) 3 (D) 4

Ans. (C)
CH3
CH3 H+
23. (X) (Major)
OH
Product (X) is :
CH3 CH3 CH3 CH3
(A) (B) (C) CH3 (D)
CH3 CH3 CH3
Ans. (A)

OH +
H
24.
5ºC
P . The product P is :

OH
(A) (B) (C) (D)

Ans. (D)
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OH
H2SO4
25. X ; X is :

OH
OH OH O
(A) (B) (C) (D)
OH
Ans. (D)

a b
26. c The double bond which is most reactive towards electrophile :
O
(A) a (B) b (C) c (D) None
Ans. (B)

27. How many products are obtained in the given reaction :

Et Ph CH3 Ph
H2SO4
HO OH + HO OH

Et Ph CH3 Ph
(A) 1 (B) 2 (C) 3 (D) 4
Ans. (B)
28. What is the order of reactivity with HBr :

(a) (b) (c)

CH3O CH3O

(A) a > b > c (B) b > a > c (C) c > b > a (D) b > c > a
Ans. (B)

OH
29. 'P' (Major Product)
O

O O
(A) (B) O (C) (D)
O O OH
Ans. (B)

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30. Arrange the following compounds in decreasing order of electrophilic addition :

O–CH 3 Cl

'P' 'Q' 'R'

(A) P > Q > R (B) P > R > Q (C) R > P > Q (D) R > Q > P
Ans. (B)

C = CH2
HBr
31. H D Product (without rearrangement of carbocation )
CCl4

CH3
What is stereochemistry of product :
(A) Racemic mixture (B) Optically inactive
(C) Mixture of diastereomers (D) Meso product
Ans. (C)

HBr
P
32. (i)CH3I If P & Q are the major products then P & Q are respectively ?
N (ii)HBr
Q

Br Br
; ; Br
(A) N N I
–
(B) N Br N I
–

Br Br
; ; Br
(C) N Br N I
–
(D) N N I
–

Ans. (C)
33. In the given reaction :
H
N Br2
[X],[X] is

H H
Br N
N N
Br N
(A) (B) (C) Br (D)
Br Br Br

Ans. (D)

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34. Select incorrect statements about product (P) of the reaction :

H Me
Br 2/CCl4
P
Me H
(A) P is optically inactive due to internal compensation
(B) P is optically inactive due to the presence of plane of symmetry in the molecule
(C) The structure of P can have three optical isomers possible
(D) P can have four possible optical isomers
Ans. (D)
CH3
HOH
35. H I Products. (If 96% racemisation takes place)
Et
Find out the correct statement about the reaction.
(A) Among the products 48% S and 48% R configuration containing molecules are present
(B) Among the products 50% S and 50% R configuration containing molecules are present
(C) Among the products 48% S and 52% R configuration containing molecules are present
(D) Among the products 52% S and 48% R configuration containing molecules are present
Ans. (C)

36. When ethyl bromide is treated with moist Ag2O, the main product is :
(A) Ethyl ether (B) Ethanol (C) Ethoxy ethane (D) All these
Ans. (B)

37. When ethyl bromide is treated with dry Ag2O, the product is :
(A) Ethyl ether (B) Ethanol (C) Ethoxy ethane (D) All of these
Ans. (C)

38. Which reaction conditions (reagents) is suitable for the following reaction :

?
H – C – OH Br – C – H
D D
(A) Br2/CCl4 (B) SOBr2 (C) PBr3 (D) HBr / conc H2SO4
Ans. (C)

39. In the given reaction

(i) SH(1eq.)
(ii) KOH
CH3 – CH – CH2 – CH2 – CH – CH3 (X), X will be.

OTs OTs

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OTs S S S

(A) CH3 – CH – CH2 – CH2 – CH – CH3 (B) CH3 – CH – CH2 – CH2 – CH – CH3

CH3 CH 3
(C) CH3 S CH3 (D)
S

Ans. (C)

CH3

TsCl KSH
40. H OH (A) Products.

Et
(1 mole)
(Assuming all the substrate convert into substitution products containing 0.05 mole of S-configuration) Calculate
the percentage of SN2 mechansim.
(A) 90 % (B) 80 % (C) 70 % (D) 95 %
Ans. (A)

NBS Na/ ether

41. CCl4. Peroxide (X) ; X is

(A) (B)

(C) (D) None of these

Ans. (C)

42. Consider the following reactions

Cl2/hv Total number of monochlorinated product = X (Excluding stereoisomers)

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Cl2/hv
Total number of monochlorinated product = Y (Excluding stereoisomers)

Identify value of X + Y.
(A) 8 (B) 9 (C) 11 (D) 10
Ans. (A)
Br
43. In the given reaction :

and
(A)
20% 80%

+
(B)
20% 80%

(C) (D)
100% 100%
Ans. (B)
44. Number of following reactions which produces hydrocarbon as major product ?
O
Na Electrolysis
(i) CH 3 – CH 2 – Cl (ii) CH3 – C – OK
Et2O
Br2
CH2 – CH2 dust
(i) Hg(OAc)2/H2O
(iii) (iv) (ii) NaBH4
Cl Cl
Br2 (i) B2H6-THF
(v) CCl4
(vi) CH3 – CH 2 – CH = CH2 (ii) CH COOH/H O
3 2

(A) 2 (B) 4 (C) 5 (D) 6

Ans. (B)

H3C CH3
(B) C=C + HI B
H3C H

45. Find out the number of 1–2–shifts during the conversion of

–
B /
–BH


(A) 2 (B) 3 (C) 4 (D) 5

Ans. (B)

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46. Select reactions from the following showing incorrect product formations -

OH
Cl
Red P
(A) CH3 COOH CH2 COOH (B) PCl3
Cl2

Me Me
Me Me
PCl5 Cl
PCl5
(C) (D) Me CHO Me CH
O
Cl
H H

Ans. (C)

47. Chloral + Cl 

Conc.H 2SO4
 product. The product is

(A) Lindane (B) DDT (C) Teflon (D) Ethaneperchlorate

Ans. (B)

48. In the following carbocation, H/CH3 that is most likely to migrate to the positively charged carbon is :

H H
1 2 + 4 5
H 3C C C C CH3
3
HO H CH3

(A) CH3 at C – 4 (B) H at C – 4 (C) CH3 at C – 2 (D) H at C – 2

Ans. (D)

49. AgCN H2 .Ni

Br   A  B
The final product (B) is :

H
NH2
(A) (B) N (C) N (D) NH2
H
Ans. (B)
50. A solution of (+) -1-chloro-1-phenylethane in toluene racemises slowly in the presence of small amount of SbCl5,
due to the formation of
(A) Carbanion (B) Carbene (C) Free-radical (D) Carbocation
Ans. (D)

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51. Identify the set of reagents/reaction conditions 'X' and 'Y' in the following set of transformations -
X Y
CH3–CH2–CH2Br  Product  CH3–CH–CH3
Br
(A) X = dilute aqueous NaOH, 20°C, Y= HBr/acetic acid, 20°C
(B) X = concentrated alcoholic NaOH, 80°C; Y = HBr/acetic acid, 20°C
(C) X = dilute aqueous NaOH, 20°C, Y = Br2/CHCl3, 0°C
(D) X = concentrated alcoholic NaOH, 80°C; Y = Br2/CHCl3, 0°C
Ans. (B)
52. Identify major product of reaction ?
Br2 Alcoh. NBS

h

KOH/ 
  product

Br
(A) (B) Br (C) Br (D)
Ans. (B)
53. The correct nucleophilicity order is :

ONa ONa ONa

ONa

(1) CH3 OCH3 Cl

(2) (3) (4)

(A) 1> 2 > 3 > 4 (B) 3 > 2 > 1 > 4 (C) 3 > 2 > 4 > 1 (D) 2 > 1 > 3 > 4
Ans. (B)
54. Which one is correct for the products of the given reaction

Me
Me
H aqueous acetone
CN 
H H
H
Cl

OCH3

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Me Me Me
Me Me Me
H H H
CN CN HO CN
H H OH H H H
H H H
OH H H

OCH3 OCH3 OCH3

(X) (Y) (Z)

(A) only X and Z are formed (B) Z > Y (amount)

(C) X > Y (amount) (D) Y > X (amount)
Ans. (D)
55. Which one will undergo hydrolysis (solvolysis) more rapidly amongst the given pairs of compounds
(X) (Y)

Br
(I)
Br

Cl
Cl
(II)
HO

(III)
I Cl

(IV) Br
Br

I II III IV
(A) x> y y>x x> y x> y
(B) y>x y>x x> y x> y
(C) x> y x> y y >x y>x
(D) y>x y>x x> y y>x

Ans. (D)

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56. The correct order of SN2/E2 ratio for the % yield of product of the following halide is

Ph
(P) CH3 CH2 C CH3 (Q) CH 3 CH CH CH 3
I Ph I

(R) CH3 – CH2 – I (S) CH 3 CH 2 CH CH 3

I
(A) R > S > Q > P (B) R > Q > S > P (C) P > R > S > Q (D) Q > P > R > S
Ans. (A)

57. The structure of the starting material X is :

PBr3 Mg/Ether
Y Z H3O 
X Na2Cr2O7,H2SO4 S   3, 4- Dimethyl - 3 - hexanol
W

OH
(A) OH (B) (C) OH (D)
OH
Ans. (B)

NaSMe
58. Br 
DMSO
 Major product
Cl

D D
(A) Br (B) Br
SMe SMe

D D
(C) MeS (D) MeS
SMe SMe

Ans. (A)

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Multiple Choice Exercise

14
HI
Br – CH – CH = CH2
1.
CH3
Products which can be obtained during the reaction in good yield :
14 14
(A) Br – CH – CH –I (B) I – CH – CH – Br
CH3 CH3 CH3 CH3

14 14
(C) Br – CH – CH2 – CH2 – I (D) I – CH – CH2 – CH2 – Br

CH3 CH3
Ans. (A,B)

2. Consider the given reaction

CH3
NaCN
H C OTs CH3CH2CH – CN
(DMF)
C2H5
CH3
which of following statements is/are correct for the above reaction.
(A) Product formation takes place due to the breaking of O – Ts
(B) The reaction is SN2
(C) The reaction is SN1
(D) Configuration of product is (R)
Ans. (B,D)
3. Correct statement (s) for the product (s) of following reaction.
CH2 = CH CH2 – Ph 
Cl2 500ºC

(A) Four different products are formed
(B) Two optically active products are formed
(C) The optically active compound formed here can also be made by the reaction of HCl
(D) The reaction path is free radical substitution
Ans. (A,D)
4. In which product formation takes place according to Hoffmann’s rule

t-BuOK CH3CH2OK
(A) CH3CH2 – CH – CH3 (B) CH3 – CH2 – CH – CH3

Br Br

CH3
OH
(C) CH3CH2 – CH – N OH (D) CH3CH2CH – CH3
CH3
CH3
CH3 S(CH3)2

Ans. (A, C, D)

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5. Which of following are correct for given reaction

N OH

H3C

(A) Major product of reaction is N (B) Major product is N

(C) The reaction is thermal elimination reaction (D) The reaction is E2 reaction
Ans. (A, C, D)

6. In which case incorrect products are formed :

HI
(A) Me3C – O – CH3   Me3 C – OH + CH3I
HI
(B) H3C – O – CH2 – CH3   CH3 OH + ICH2CH3

HI
(C) O – CH2 I+ CH2 – OH

OH
HI
(D) Anisole  + CH3I


Ans. (A, B C)

7. In the given reaction : NBS

Find out the correct statement

(A) It gives total 9 allylic brominated products
(B) 6 fractions are obtained on fractional distillation of product mixture
(C) Substrate has 7 allylic hydrogens
(D) NBS is a brominating agent for allylic positions
Ans. (A, C, D)

8. Product obtained in given reaction in good yield are :

HBr

(A) (B)
Br

Br

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(C) (D) Br

Br
Ans. (A, B)

H+
OH
9. 1.eq.
OH
Correct statements for given reaction :
(A) Product mixture is resolvable
(B) Product can be separated by fractional distillation of mixture
(C) Two products possible & both are optically active
(D) Products are diastereomer
Ans. (A, C)

10. Which of the following can be formed during this reaction ?

H3O+

OH

OH

(A) (B)
OH OH

(C) (D)
O O
Ans. (A, B, D)

Na
11. Product
in Et2O
Cl
Cl
Correct statement is / are :
(A) odd no. of double bond equivalent in product
(B) product is bicyclic compound
(C) product can show geometrical isomerism
(D) reaction involve carbocation as intermediate
Ans. (A, B, C)

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12. Ph – CH = CH2 + BrCCl3 

Peroxide
  Product is :
H H
(A) Ph CH2CCl3 (B) Ph CH2Br

Br CCl3

Br CCl3
(C) Ph CH2CCl3 (D) Ph CH2Br

H H
Ans. (A, B)

CH3 Cl

13. Na/(Dry ether)

CH3  
CH2 Cl

Products obtained in above Wurtz reaction

CH3
(A) (B)

CH3 CH3 CH3

CH3

(C) (D)
CH3 CH3 CH3

Ans. (A, B)
14. Select the correct informations about product in reactions I and II.

H Br

NaI/Acetone
(I)
AgF (Protic solvent)
(II)

H3C H

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(I) (II)

H CH3 H CH3 H CH3

(A) +

I H F F H
H

H I I H H F

(B)

H3C H H3C H H3C H

I CH3 F H F CH3

(C) +

H H CH3 H H
H

(D) SN2 SN1

Ans. (A, D)
15. Which of the following can be the product/s of following reaction

Me

H NaOH
Br  
D

Me H Me OH

(A) H (B) Me (C) HO (D) H

D OH H Me
OH D D D

Ans. (A, B, C, D)
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16. The correct statement/s about the following is / are

CH3
I*
NaI / Acetone
  'Y'

(A) The product is achiral compound

(B) The product does not have isotopic iodine
(C) It is an allylic biomolecular nucleophilic substitution reaction
(D) Ozonolysis product of ‘Y’ give positive iodoform test
Ans. (A, B, C, D)

17. Which of the given compounds can be the main products of following reaction
Br2 /aq.NaCl  NaI  NaNO3
CH3 – CH = CH2  

(A) CH3 CH CH2 (B) CH3 CH CH2 ONO2

Br Cl Br Cl

(C) CH3 CH CH2 (D) CH3 CH CH2

I Br OH Br

Ans. (C, D)

18. Enthalpy

Reaction co-ordinate

out of the following which one is/are correct

NO2 

E E

(A) 1, + H (B) 2, E (C) 3, H (D) 4,

H
H E
Ans. (A, B, C, D)

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NBS HBr
19. CCl4/hv (X) + (Y) enantiomeric pair

Br Br Br
Br
(A) (B) (C) (D)
Br Br Br

Br
Ans. (B, D)

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Mis. Exercise
Subjective
1. Encircle whichever of the following :

CH3
(a) undergoes an S N 2 reaction more rapidly : CH2 Br or
Br

CH3 CH3
CH CH2 CH2 C CH2 CH3
(b) Undergoes an E1 reaction more rapidly : Br Br
or

Br

(c) Undergoes an S N reaction more rapidly :

1 or
Br

Cl
Cl

(d) Undergoes an S N 2 reaction more rapidly : or

Cl

Cl
(e) Undergoes an E2 reaction more rapidly : or

2. Select which reaction from the following reaction pairs will occur faster .
PART-1

I OH
H2 O
CH3 CH3
Reaction A DMSO

I OH
H2O
H H
Reaction B DMSO

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PART-2

Cl I
NaI
Reaction C CH3 DMSO CH3

CH2Cl NaI CH2l

Reaction D DMSO

PART-3

I Cl
NaCl
Reaction E H DMSO H

I Cl
NaCl
Reaction F H EtOH H

PART-4

I N3
NaN3
Reaction G H DMSO H

Br N3
NaN3
Reaction H H DMSO H

PART-5

CH2 Cl CH2 I

NaI
Reaction I
acetone

Br I

NaI
acetone
Reaction J

CH3 CH3

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O
PCl5 x NaNH2 CH3I
3. Reaction- 1 : Ph C CH3 Ph C C CH3

Br y NaNH2
CH3 C C CH3
Reaction - 2 :
Br

Reaction - 3 : Ph CH CH 2 z NaNH2 Et-I

Ph C C Et
Cl Cl
x,y,z are moles used.
Sum of [x + y + z = ]

4. Sum of hydrogen in major product of the reaction.

OH

H+
Reaction -1 (A)


OH

H+
Reaction-2 (B)


OH

Reaction 3 H+
(C)


OH

Reaction-4 H+
(D)


Sum of -hydrogen is A + B + C + D =

5. Select whether the following reagent combination will result in elimination or substitution reactions leading to the
major product.
Reaction Substitution Elimination

CH3

K OC(CH3)3
(a) CH3 C Cl

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CH3
H2SO4
(b) CH3 C OH

CH3

Cl
(c) CH3 CH CH2 CH3 alc-KOH

CH3 
Na N3
(d) CH3 C l

Cl
CH3 EtO–
(e) 

CH3
(f) CH3 C Cl
CH3
6. RCl is treated with Li in ether to form R – Li, R – Li reacts with water to form isopentane. R – Cl also reacts with sodium
to form 2, 7 – dimethyloctane. What is the structure of R – Cl .

7. A chloroderivative ‘X’ on reduction gave a hydrocarbon with five carbon atoms in the molecule . When X is
dissolved in ether and treated with sodium, 2, 2, 5, 5-tetramethyl hexane is obtained.
What is compound X.

8. With the help of following data show HBr exhibits the peroxide effect.
H10 / kJmol –1 H 02 / kJmol –1
   
H–H X  CH 2  CH 2  XCH 2 – C H 2 XCH 2 – C H 2  H  X  XCH 2 CH 3  X

HCl – 67 +12.6
HBr – 25.1 – 50.2
HI + 46 – 117.1

9. What are the products of the following reactions ?

(a) Ph CH = CHCH3 + HBr A
H3C CH3
(b) C=C + HI B
H3C H

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CH3
Peroxide
(c) +HBr C

CH3
+HCl D
(d)
CH2CH3

10. If required 0.7 g of a hydrocarbon (A) to react completely with Br2 (2.0g) and form a non resolvable product. On
treatment of (A) with HBr it yielded monobromo alkane (B). The same compound (B) was obtained when (A) was
treated with HBr in presence of peroxide. Write down the structure formula of (A) and (B) and explain the reactions
involved .

11. Complete following reaction

H CHl Br2 Cl2

(A) CH2 (B) CCl4 (C) CS2

CH3
CH3

12. CH  C – CH2 – CH = CH2 , adds up HBr to give CH  C – CH2 – CHBr – CH3 while CH  C – CH = CH2 adds up HBr
to give CH2 = C. Br. CH = CH2.

13. What are the products of the following reactions?

CH3 CH3
(a) CH3 – C – Cl + OCH3 (b) CH3 – C – O+ CH3 –X

CH3 CH3
14. A primary alkyl bromide (A) C4H9Br reacted with alcoholic KOH to give compound (B). Compound (B) reacted with
HBr to give an isomer of (A) . When (A) was reacted with sodium metal it gave compound (D), C8H18, which was
different from the compound produced when n- butyl bromide was reacted with sodium. Draw the structure of (A)
and write equations for all the reactions .
15. In study of chloronation of propane four products (A, B, C, D) of molecular formula C3H6Cl2 were obtained. On
further chloronation of the above products A gave one trichloro product, B gave two whereas C and D gave three
each. When optically active C was chlorinated one of trichloro propanes was optically active and remaining two
were optically inactive. Identify the structures of A, B, C and D, and explain formation of products. Total number of
vicinal dichloride are :
16. The maximum number of isomers (including stereoisomers) that are possible on mono-chlorination of the following
compound, is

CH3
C
CH3CH2 CH2CH3
H

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Comprehension
Paragraph - 1 (17-18)
17. Select whether the following combinations of reactants will react by substitution ( SN1 or S N 2 mechanism), elimi-
nation (E1 or E2 mechanism)

NaI in acetone
Br
A. 25°C

(a) SN1 (b) S N 2 (c) E1 (d) E2

Cl
B. NaOCH3 in methanol
0
50 C

(a) SN1 (b) S N 2 (c) E1 (d) E2

Cl
NaOCH3 in methanol
C. 250C

(a) SN1 (b) S N 2 (c) E1 (d) E2

D. (CH3)3 C OH HBr 48%

0
in H2O
25 C

(a) SN1 (b) S N 2 (c) E1 (d) E2

NaCN in ethanol
E. (CH3)2 CH Br 0
25 C

(a) SN1 (b) S N 2 (c) E1 (d) E2

H H

Br NaCN in ethanol
F. 0
25 C

(a) SN1 (b) S N 2 (c) E1 (d) E2

HBr 48%in H 2O
G. (CH3)2 CHCH 2CH2 OH 0
50 C

(a) SN1 (b) S N 2 (c) E1 (d) E2

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X
E2 reaction
18. +
(Hoffmann product) (Saytzeff product)

(A) In the above reaction, maximum Saytzeff product will obtained when :
(a) X = -I (b) X = -Cl (c) X = -Br (d) X = -F
(B) In the above reaction Hoffmann product is major when X is :
(a) -I (b) -Cl (c) -Br (d) -F
Passage (19-20)
A flask contains “mixture” of unknown Alkenes obtained by treatment of 2-chlorobutane with alc. KOH. When the
“mixture” is boiled, the fraction that comes our firstly is A.
19. A on Hydrogenation followed by Treatment with Cl2/h gives how many monochloro products (only structural
isomers)
(A) 1 (B) 2 (C) 3 (D) 4

20. The remaining Alkene mixture is ozonolysed carefully in presence of Zinc and Products atr treated with mixture of
NH2OH. How many oximes obtained.
(A) 2 (B) 3 (C) 4 (D) 5
Passage for (21-23)
Observe the following reactions and given answers

O
OC H CH2CH3

C HCOOH C + C
H3C CHCH3 H3C CH2CH3 H3C OC H
(I)
Ph Cl Ph Ph O

N3
H CH2CH3
C N3 C CH2CH3
Ph (II)
H
Cl
Ph

Br Ag+/H O OH
2

(III)
Br Br

Br
H2O
C C
(IV)
Br O

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21. Which of the following structure represents the transition state of slow step of reaction I.

Cl
H H
H H
C C C C
CH3 CH3
(A) H3C Ph (B) H3C Ph
O C H O C H
O O

CH2 CH3
Cl
C Cl H
H
(C) H3C (D) C C
Ph CH3
H3C Ph

22. Which of the reaction (I-IV) involves rearrangement of reaction intermediate.

(A) I only (B) I, III (C) II, III, IV (D) I, II, III
23. Planar reactive intermediates are formed in reactions :
(A) I, III (B) II, III (C) I, II (D) I, III, IV
Comprehension (24-26)
Observe the following experiment

24. If the reactant ‘P’ is ethyl chloride then the product R can be

(A) (B) CH3CH2 – O – CH2CH3

(C) (D)

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25. If the liquid Q is H  C  OC2H5 then the product R can be (P can be any other halide)
||
O

(A) (B) (C) (D)

26. If R is then P and Q can be respectively..

(A) , CH3 – – OC2H5 (B) CH3 – Cl,

(C) CH3 – – CH3, (D) , CH3Cl

Match The Column

27. Matrix :
Column (I) Column (II)
Compound Type of reaction

Cl

(A) (p) SN1 reaction can take place

Cl
(B) (q) S N 2 reaction can take place

Cl

(C) (r) SN1 is not possible

Cl
(D) (s) S N 2 is not possible

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28. Match the column :

Column (I) Column (II)
E2 reaction No of possible products.
(elimination bimolecular) (including stereoisomerism)

Br
(A) alc.KOH (p) 0


alc.KOH
(B)  (q) 1
Br

alc.KOH
(C)  (r) 2
Br

alc.KOH
(D) Br (s) 3

29. Match the Column :
HEM = Hoffmann exhaustive methylation followed by elimination.
Column (I) Column (II)
Reaction Product

(A) HEM HEM (p) H2C CH CH2 CH CH2

N
H

(B) HEM HEM (q) H 2C CH CH2 CH2 CH CH2

N
H

CH3

(C) HEM HEM (r) H2C CH CH2 C CH2

N
H
CH3

(D) HEM HEM (s) H2C CH CH CH CH2

N
H

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30. Match the column

Column-I Column-II

Ph
(A) Ph (P)
OH

(B) (Q)
OH

OH
(C) (R)

(D) OH (S)

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31. Match the mechanism/s mentioned in List-2 with reactions of List - 1. More than one options of List- 2 can match
with one reaction of List-1.
List -1 List -2
Reactions Mechanism

CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3

C2H5OH/ C OC2H5
(a) CH3 C C C Cl CH3 C C C CH2 + CH3 C C (P) = SN1
CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3

H H CH3ONa/CH3OH/60° + H H3CO
(b) (Q) = E1Cb
CH2 H CH2 H
CH3 I

CH3 H H I
(c) NaI/Acetone (R) = E1
H Cl reflux
H3C H

(d) Ph C NaOH/ (S) = E2

CH2 CH CH3   Ph C CH CH CH3
O OH O
(T) = SN2

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Single Choice Exercise

1. Cl /h 
2
n  Butane  
Give the total number of monochloro products (including stereoisomers), which are possible in the reaction.
(A) 2 (B) 3 (C) 4 (D) 5
Ans. (B)

2. Double bond equivalent of cubane is

Cubane

(A) 4 (B) 5 (C) 6 (D) 7

Ans. (B)

Cl2
3. CH3 CH CH2 CH3 (x) = Number of monochloro product including stereoisomers.
h
CH3
(A) 4 (B) 5 (C) 6 (D) 7
Ans. (C)

ND2-ND2
4. (P)
H2O2

Product (P) is :

D D
(A) (B) (C) (D) both (B) & (C)
D D

Ans. (B)

H + H2 Pd
5. CH2
CH3

Product of the above reaction will be

(A) Racemic mixture (B) Diastereomers (C) Meso (D) Constitutional isomers
Ans. (B)
6. Among the following free radical bromination reactions, select those in which 2° halide is the major product -

CH2-CH3

Br2/h Br2/h Br2/h

(P) (Q) (R)

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Br2/h Br2/h
(S) (T)

Br2/h
(U)
(A) P,Q,R,S (B) P,R,U (C) P,R,S,T (D) P,Q,R,S,T
Ans (B)

7. Select the chain propagation steps in the free-radical chlorination of methane.

(1) Cl2  2Cl (2) Cl+ CH4  CH3Cl+H

(3) Cl  CH 4  CH 3  HCl (4) H + Cl2  HCl + Cl

(5) CH 3  Cl 2  CH 3Cl  Cl 
(A) 2,3,5 (B) 1,3,6 (C) 3,5 (D) 2,3,4
Ans. (C)

CH3

Br2/h Monobromo derivatives

8.

The number of possible monobromo products is (excluding stereoisomers) :

(A) 4 (B) 5 (C) 8 (D) 10
Ans. (B)

CH3 CH CH3 H /Pt

9. C C 2

D D

Product of the above reaction will be :

(A) Racemic mixture (B) Diastereomers (C) Meso (D) Constitutional isomers
Ans. (A)
10. Rank the transition states that occur during the following reaction steps in order of increasing stability
(least  most stable) :

1. H 3 C  O H 2  CH 3  H 2 O


2.  CH3 3 C  O H 2   CH3 3 C  H 2O

3.  CH 3 2 CH  O H 2   CH3 2 CH   H 2O
(A) 1 < 2 < 3 (B) 2 < 3 < 1 (C) 1 < 3 < 2 (D) 2 < 1 < 3
Ans. (C)

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11. (R)-3 bromocyclopentene (shown below) reacts with Br2/CCl4 to from two products, Y and Z, Y is not optically active
(does not rotate plane-polarized light). What is the structure of Y ?

Br2 /CCl4
 Y  Z

Br

Br Br Br

(A) (B) (C)

Br Br
Br Br Br Br

Br
(D) (E)
Br Br Br

Ans. (C)

+
o H
12. Major product of the reaction :

OH
HO
(A) (B)

(C) OH (D)

OH
Ans. (B)

O3 H2/Ni H+
13. A B (C) ; Product (C) of the reaction is :
Zn 

OH O

(A) (B) (C) (D)

Ans. (C)

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Br2
14. OH W. Product W is :
CH2Cl2

OH
(A) (B) Br
Br Br OH

OH
(C) Br (D)
O Br
Ans. (C)
15. What is a likely product of the reaction shown ?

H3C H
Br2 /CH3OH
CH3 

Br OCH3 H CH3
H3C CH3 H3C
H3C
Br OCH3
CH3
(A) (B) CH3 (C) (D) CH3
OCH3 Br
Br
Br
Ans. (D)
16. How many transition states and intermediates will be formed during the course of following reaction?

OH
+
H2O,H

(A) 3 transition states and 3 intermediates (B) 4 transition states and 3 intermediates
(C) 3 transition states and 2 intermediates (D) 5 transition states and 4 intermediates
Ans. (B)
17. The product (s) of the following reaction can best be described as :

HBr
 

(A) a racemic mixture (B) a single enantiomer (C) a pair of diasteriomers (D) an achiral molecule
Ans. (C)
18. How many products will be formed in this reaction ?

1. OsO4
2.NaHSO3

(A) 10 (B) 2 (C) 3 (D) 4

Ans. (B)

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cess)
H2 (ex
Pt CO2H
19. A KMnO CO2H
4
+
CO2H CO2H
Compound (A) is :

(A) (B) (C) (D)

Ans. (B)
20. What is the major product expected from the following reaction ?

KMnO 4
–
HO cold

OH OH
OH OH
OH H H
OH H O
(A) (B) H (C) OH (D)

Ans. (B)
21. Which of the following is a major product of the reaction shown below ?

CH3
Br2
H 2O

CH3 CH3 CH3 CH3

Br OH Br OH
(A) (B) Br (C) (D)
OH H H
H H OH Br

Ans. (D)
22. Which of the following compound was the starting material for the oxidation shown below ?

O
KMnO 4 /H  HO
?  OH + CO2
O OH

(A) (B)

(C) (D)

Ans. (B)

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
23. The reaction, (CH3)2C = CH2+ Br  (CH 3 ) 2 C  CH 2 Br is an example of a/an ........ step in a radical chain
reaction.
(A) initiation (B) termination (C) propagation (D) heterolytic cleavage
Ans. (C)

COOH
Br2
24. HOOC HOOCCH(Br)CH(Br)COOH
CCl4
(X)
P
Br2
HOOC COOH HOOCCH(Br)CH(Br)COOH
Q CCl4

(Y)
The correct statements with respect to the above pair of reactions are that
(I) the reactions are stereospecific
(II) (X) is erythro and (Y) is threoisomer
(III) (X) is threo and (Y) is erythro ismer
(IV) each of (P) and (Q) gives a mixture of (X) and (Y)
(A) I and II (B) I and III (C) I and IV (D) II and IV
Ans. (A)

O O
R' R
C C CH3 S CH3 Product A + CH3 S CH3
25.
H R dimethyl sulfide
O O

Product A of the above reaction is :

O
(A) R C R (B) R CHO (C) R  CO2 H (D) both (A) and (B)
Ans. (D)

CH3
H (1) BH3 ; THF (A) ; Product of the reaction is :
26.
–
(2) H2O2, HO

CH3 CH3 CH3 CH3

H OH H H
(A) H (B) H (C) OH (D) H
OH H H CH3

Ans. (A)

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CH 3
1.BH 3/THF
27. – A ; Product A is ;
2. H 2O 2/OH

CH3 CH3 CH3

CH3
H H
(A) (B) (C) OH (D)
H OH
OH
OH H
Ans. (D)

CH 3
1.Hg (OAc)2.H 2O
28. A; Product A is ;
2. NaBH 4

CH3 CH3 CH3

CH3 OH
H
(A) (B) (C) OH (D)
H H
OH OH CH3 H
Ans. (D)

29. Choose the correct product of the following reactions :

O
CH3 Cl OOH
1.
+
CH3 2. H3O

OH
CH3

CH3 OH

(A) CH3 (B) OH

H CH3

CH3
OH
OH
CH3
(C) CH3 (D)
H
OH
CH3
Ans. (C)
30. Compound A, which is a degradation product of the antibiotic vermiculine has following structure

O O
C CH CH2 CH CH C
CH3 CH CH2 C OCH3
O

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(A) H2 (B) (CH3)2S O3 (C) . Unknown (C) is :

C11H14O4 Pd/C C11H18O4 CH2Cl2 C11H18O2

CH2
C CH2 CH CH
(A) CH3 CH2 C C O CH3
CH2 O

CH2 O
C CH2 CH2 CH2 C
(B) CH3 CH2 CH2 C CH2 OCH3
CH2

CH2 O
C CH2 CH2 CH C
(C) CH3 CH2 CH2 C CH2 OCH3
CH3

(D) None of these

Ans. (B)

(a)
cis -3- hexene 
31.  meso 3,4 - hexanediol
(b)
trans-3- hexene   meso 3,4- hexanediol.
Choose pair of regent (A,B) for above conversions.
(A) Cold KMnO4 , OsO4 (B) Cold KMnO4, RCO3H/ H3O+
(C) RCO3H/H3O+ , cold KMnO4 (D) None of these
Ans. (B)

Na O3 Ph3P=CH2(2mole)
32. (A) (B) (C)
Liq. NH3 Zn

Product (C) of the above reaction is :

(A) 1,3 hexaidene (B) 1,4 pentadiene (C) 1,3 butadiene (D) 1,3 heptadiene
Ans. (B)

33.

To achieve above conversion, the regents used will be :

(A) O3/ H2O2, HO– / (B) HBr, alc. KOH, O3, LiAlH4, H+ / 
(C) HBr, t- BuOK, O3, KMnO4, (D) HCl, KMnO4 (cold), H+ /
Ans. (B)

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1. Hg(OAc)2
34. A Product (A) of the above reaction is :
OH 2. NaBH 4

O O O O
(A) (B) (C) (D)

Ans. (B)

35. Decreasing order of rate of reaction of molecules towards electrophilic addition reaction is :

CH = CH2 CH = CH2 CH = CH2 CH = CH2

NO2 OH CH3 NH2

(a) (b) (c) (d)

(A) a > b > c > d (B) b > c > a > d (C) d > b > c > a (D) b > d > c > a
Ans. (C)

H2SO4
A;
36. 

OH

(A) (B) (C) (D)

Ans. (B)

37. Br2 Stereochemistry of the product is :

CCl4

H CH3

(A) Diastereomers (B) Racemic mixture (C) Meso (D) Pure Enantiomers
Ans. (A)

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Br2
CCl4
38. Product/s obtained is / are :
H CH3

(A) Diastereomers (B) Racemic (C) Meso (D) Optically pure enantiomers
Ans. (B)

HO
39. H3O+
A

Product (A) of the reaction is :

OH OH

(A) (B)

(C) (D) None of these

Ans. (A)

40. Br2/hv Major (X) Alcoholic Major (Y) H-Br Major (Z):
KOH/ Peroxide

Product (Z) is :

Br
Br
Br
(A) (B) (C) (D)
Br

Ans. (C)
41. The reaction of HBr with the following compound would produce :

OH

Br
OH OH
(A) (B)
Br

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Br
Br Br
(C) (D)
Br
Ans. (B)

O
C CH3 (1)3NaNH 2
PCl5 min eral oil
42. 
0 C
 (A) 
(2)H 
 (B) ; Product (B) is
70 80% 46%

CH CH2 C CH CH2
(A) (B) (C) (D)

Ans. (B)

Br2 (i)alc.KOH
43. 
CCl 4
 
(ii) NaNH 2
 (A) ; Product (A) is :
major

(A) H2C = CH – CH= CH2 (B) CH3 – C  C – CH3 (C) CH3 – CH2 – C  CH (D) CH3 – CH = C = CH2
Ans. (B)

O
NaNH 2 H
44. CH3CH2C  CH 
liq.NH3
I J  (K)
Et2O
Product (K) of the above reaction is :

O OH
C C Et
(A) C C Et (B)

OH OH
C C CH2 CH3 C C CH3
(C) (D)

Ans. (B)
(CH3 ) 2 SO4
45. CH 3  CH 2  CH 2  C  CH  LiNH 2 
(A)  (B)
Lithium
amide

Give the structural formula of compound (B) :

(A) CH3 – (CH2)2 – C  C – SO3H
(B) CH3 – (CH2)2 – C  C – CH3

O
(C) CH3 – (CH2)2 – C  C – CH2 – O S H
O
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(D) CH3 – CH2 – C  C – CH2

Ans. (B)

CH2 CH2 CH3

46. ; This conversion can be achieved by :

(A) NaNH2, CH3CHO (B) NaNH2, CH3 – CH2 – CH2 – Br

(C) KOH, CH3 – CH2 – Br (D) KOH, CH 2 CH2

Br Br
Ans. (B)

Cl
3NaNH 2
47. Ph C CH3   (A) ; Product (A) is ;
Pr oduct
Cl

(A) Ph – CH = CH2 (B) Ph – C  CH (C) Ph – CH2 – CH3 (D) Ph C CNa
Ans. (D)

(i )NaNH 2 ,NH 3 H2
48. C CH (ii )CH 3Br
(A) 
Lindlar catalyst
(B) ; Product (B) is

H H
H CH3 C
C C CH3 C H
C C
(A) (B) H (C) C H (D)
C H
CH3
Ans. (C)
49. What is the final product, C, of the following reaction sequence ?
1.N aNH 2
H  2.CH
  
3 CH 2 Br
A

1.Na, NH3 (liq.)

A  B

Br2
B 
CH2Cl2
C

Br Br
Br
(A) (B)

Br

Br Br

(C) (D)

NH2 Br
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Ans. (A)

Compound (X)
5H2 CH2 CH2 CH2 CH3
Pt

AgNO3
50. Precipitate

O O O O O O
O3 CHO
H C CH2 CH2 C C H + H C C O H + H C O H +
Me2S CHO

Compound (X) will be :

(A) CH CH C CH (B) CH CH2 C CH

(C) CH CH2 C CH (D) C CH C CH

Ans. (A)
51. How much volume of air will be needed for complete combustion of 10 lit. of ethane -
(Assuming that approx 20% O2 is present in air)
(A) 135 lit. (B) 35 lit. (C) 175 lit. (D) 205 lit.
Ans. (C)
52. During the preparation of ethane by Kolbe’s electrolytic method using inert electrodes the pH of the electrolyte -
(A) Increases progressively as the reaction proceeds
(B) Decreases progressively as the reaction proceeds
(C) Remains constant throughout the reaction
(D) May decrease of the concentration of the electrolyte is not very high
Ans. (A)

O
53. COOH ; A can be
O3 /H 2O
Alkene A 
 CH3 C CH3 + CH3COOH + CH3 C
O

CHCH 3 C(CH 3)2

CH 3
(A) CH3 C CH C (B) CH3 C CH HC CH 3
CH 3

(C) Both correct (D) None is correct

Ans. (C)

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H
Ph CH3 Br2 NaI
54. 

 P(Alkene) 
CCl4
 
Acetone
Q(Alkene)
H3C Ph
OCOR

Alkene (P) & (Q) respectively are

CH 3 Ph CH 3 CH3 CH3
Ph
(A) Both C C (B) C C , C C
Ph H 3C Ph Ph Ph
H 3C

H
Ph CH3
CH3 CH3
(C) C (D) Both C C
Ph Ph
Ph CH2

Ans. (C)


H3O
55.
BH 3 / THF
B  CH2  A
H 2O2

A and B are

(A) Both CH2OH (B) Both CH3

OH

(C) CH3,OH CH3 (D) CH3 , CH2OH

OH OH

Ans. (D)
CCl3Br
56. CH2=CH–CH=CH2 
Peroxide
 Product. The major product is

(A) Br – CH2–CH=CH–CH2–CCl3 (B) CH 2 CH CH CH 2 CCl3

Br

(C) CH2 CH CH CH2 Br (D) None is correct

CCl3

Ans. (A)

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OH
 (i)O3
H
57. 

A 
(ii) Zn/H 2O
 Product(s). Product is / are ?

CHO

(A) + HCHO (B) CH O

O

O
CHO
(C) + CH3CHO (D) OHC

Ans. (B)

58. ( reagent R 2 Reagent R1

   
HO OH HO OH

R1 and R2 respectively are –

(A) Cold alkaline KMnO4, OsO4 / H2O2 (B) Cold alkaline KMnO4 , HCO3H
(C) Cold alkaline KMnO4 , CH3 – O – O – CH3 (D) C6H5CO3H, HCO3H
Ans. (B)

COOCH3
OSO 4 (leq)
59. 
H 2 O/ Acetone
X .
COOCH3

Identify ‘X’.

COOCH3 COOCH3
OH OH
(A) OH (B)
COOCH3 OH
COOCH3

COOCH3
OH OH
(C) OH OH (D) Reaction will not occur
COOCH3

Ans. (B)

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60. Identify (P) in the following reaction :

Ph H H
+2
H  /H 2O
  (P)
O

Ph Ph Ph O Ph
(A) (B) O (C) (D) O
O O O
O O

Ans. (A)

61. A mixture of CH4, C2H4 and C2H4 gaseous are passed through a Wolf bottle containing ammonical cuprous chloride.
The gas coming out is
(A) Methane (B) Acetylene
(C) Mixture of methane and ethylene (D) Original mixture
Ans. (C)
62. An organic compound of molecular formula C4H6, (A), forms precipitates with ammonical silver nitrate and ammonical
cuprous chloride. ‘A’ has an isomer ‘B’, one mole of which reacts with one mol of Br2 to form 1,4–dibromo-2-butene.
Another isomer of A is ‘C’, one mole of C reacts with only 1 mol. of Br2 to give vicinal dibromide. A, B & C are

(A) CH3 – CH2 – C  CH and CH2 = CH – CH = CH2;

(B) CH3 – C  C – CH3 and CH3 – CH = C = CH2 ; CH3 – C  C – CH3

CH2 CH2 CH
(C) C CH2 and ; CH2 = CH – CH = CH2
CH2 CH2 CH

CH
(D) CH3 – C  C – CH3 and CH2 CH2 ; CH = CH – CH = CH
2 2
CH
Ans. (A)
63. Correct statement regarding product of reaction

+ H Br
(1 eq)

(A) Kinetic controlled product is a secondary bromide whereas thermodynamically controlled product is a tertiary
bromide.
(B) Kinetic controlled product is a tertiary bromide whereas thermodynamically controlled product is a primary
bromide.
(C) Both kinetic & thermodynamic controlled product is secondary bromide.
(D) Both kinetic & thermodynamic controlled product is tertiary bromide.
Ans. (B)

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HgSO4 (1)NH3  HCN

64. H  C  C  H 
H 2SO4
(A) 
(2)H O 
(B) ; Product (B) of given reaction is :
3

(A) Glycine (B) Alanine (C) Valine (D) Leucine

Ans. (B)
65. The slowest chain propagation step of the following reaction is
R 2 O2
CH4 + SO2Cl2   CH3Cl + SO2 + HCl

(A) RO   CH 4 
 ROH  CH 3 (B)  CH 3  SO 2 Cl 2 
 CH 3Cl   SO 2Cl

(C) SO 2 Cl 
 SO 2  Cl (D) Cl  CH 4 
 HCl  CH 3

Ans. (D)
66. Observe the following diagram for relative boiling points of different alkanes. Identify the hydrocarbons X, Y, Z, W,
R.
Z
W
X
R
Y
B.P.

alkanes
X Y Z W R

(A)

(B)

(C)

(D)

Ans. (B)

H  C  CNa NaNH 2 I  (CH 2 )7  Cl NaCN H 3O H 2 /Pd/CaCO 3 /Quinoline
67. E  (1)
 
(2)
 (3)
 
(4)
 
(5)
  (6)

F (CH2)7 H2C CH2 (CH2)6 COOH

C C
H H
Identify the compound ‘E’.
(A) 1-Fluorodecane (B) 1-Bromo-8-Fluorooctane
(C) 1-Bromo-7-Fluoroheptane (D) 1-Bromo-11-Fluoroundec - 2- yne
Ans. (B)

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13

68. The compound ‘X’ OH can be synthesized by using the reagents.

13  13
Li
(I) + CH3MgBr (II) +O
O

 
O + Li13 Li
(III) (IV) +
O

(A) I and III (B) I, II, III (C) All (D) I, II only
Ans. (B)
69. The correct sequence of reagents for the following conversion is

OH

Hg(CH3COO) 2 / H 2O NaBH 4 Al2O3 dil.H 2SO 4 B2 H6 /THF H2O2 /OH dil.H 2SO4 
conc.H 2SO4
(A)  (1)
 
(2)

(3)
  (4)
 (B)  (1)
 
(2)
 (3)
 (4)

dil.H 2SO 4 Al2O3 ,  B2 H6 /THF H 2O2 /OH  dil.H 2SO 4 dil.H 2SO 4 /  Hg (CH 3COO) 2 /H 2O NaBH 4
(C)  (1)
 
(2)
  (3)
 (4) (D)  (1)
  (2)
  (3)
 
(4)


Ans. (C)
70. Which common factor is responsible for the regioselective nature of the following reactions.

Cl Cl Cl
Cl
HCl
(I) CH2 = CH – Cl    CH3 – CHCl2 (II) Cl2 /FeCl3
  +

Cl

Br Br


HBr NO 2
(III) H – C  C – Br    CH2 = CBr2 (IV)  

NO2

(A) – I effect of halogens (B) + I effect of halogens

(C) + M effect of halogens (D) – M effect of halogens
Ans. (C)

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71. In which of the following reaction the product will also be optically active

H 2 /Pd/CaCO3
* O3
(A) *   (B)  

H 2 /Ni O3
(C) *   (D)  
*
Ans. (D)

(1) NaoH
72. + (x) 
(2)H 
 O ; Reactant x is

(A) CH3Cl (B) CH2Cl2 (C) CHCl3 (D) CCl4

Ans. (C)

CHFBrI
73. 
t.BuOK
(Q)
What is the product (Q) of the following reaction ?
Cl Cl

(A) (B)

(C) (D)
Cl F
Ans. (D)

H
* C
C  
K O C(CH 3 )3
74. Br Heat
(A)

Br * 14
(C C)

* Br * Br
(A) C C (B) C C

(C) C C (D) C C

Br
Ans. (B)
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CHCl3 CHCl3
75. 
KOH
(A) 
KOH
(B) ; Product (B) is :

Cl
Cl Cl
(A) (B)
Cl
Cl Cl
Cl
(C) (D)

Cl
Ans. (C)

76. The major product formed in the following reaction is

Me Me

 :CH 2 (singlet) 

H H

Me H
Me Me
(A) (B)
H H H Me
Me CH2CH3
(C) 50 : 50 mixture of above two compounds (D)
H H
Ans. (A)
O

CH2 
Br2
(A)  CHBr3 
77. KOH

O
Product (A) of the reaction is :
CO2H CO2H CO2 CH3
(A) (B) (C) (D)
CO2H C CH3 CO2 CO2H

O
Ans. (C)

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Multiple Choice Questions

H 3 (B)
/liqN
Li
1. NaNH 2 CH 3  I H2
CH 3  C  C  H   (A) (C)
Pd-CaCO3

Relation between (B) and (C) is:

(A) Enantiomer (B) Diastereomer
(C) Geometrical isomer (D) Meso
Ans. (B),(C)

Cl

2. Na
(A) ; Product (A) is :
14 dry ether

14 14
14
14
14
(A) (B) (C) 14 (D) 14
14

Ans. (A,B,C)
H2 /Pt O3 /H 2O
3. (A)C4H 6  (B)C4 H8   CH3COOH

Hence A and B are

(A) CH3C  CCH3 , CH3CH = CHCH3 (B) CH2 = CHCH = CH2 , CH3CH = CHCH3

(C) , CH3CH = CHCH3 (D) None

Ans. (A, B)
4. CH3 – CH = CH – CH3 + CH2N2 

 A ; A can be

(A) (B) (C) (D)

N N
N N

Ans. (A, B, C, D)

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Peroxide
Ph – CH = CH2 + BrCCl3 
5.   Product is

H H Br
CCl3
(A) Ph CH2CCl3 (B) Ph CH2Br (C) Ph CH2CCl3 (D) Ph CH2Br
Br CCl3 H
H
Ans. (A, C)
6. Which of the following elimination reactions will occur to give but-1-ene as the major product ?
EtOH
EtOH
(A) CH3.CHCl.CH2.CH3 + KOH   (B) CH3.CH.CH2.CH3+NaOEt 

NMe3
+

(C) CH3.CH2.CHCl.CH3 + Me3COK+ 


 (D) CH3.CH2.CH(OH).CH3 + conc. H2SO4 



Ans. (B, C)

OH–

7. +
N

The above compound undergoes elimination on heating can yield which of the following products ?

(A) (B) (C) (D)

Me
+ CH2 CH2 Me
N N N N
Me Me Me Me Me Me Me
Me

Ans. (B, C, D)
8. Identify reagent for conversion of butene to butan-2-ol

(A) KMnO4/OH– / H2O(Cold) (B) Dil.

H2SO4

(C) (1) Hg(OAc)2/H2O (D) HOH/HgSO 4

(2) NaBH4

Ans. (B, C)
9. In which of the following cyclic transition state is formed.
500 C
(A) CH3 COOCH CH2 CH3   CH2 = CH – CH2CH3 + AcOH
CH3

(i)B2O6 /THF
(B) CH3 – CH = CH – CH3   CH3 CH CH CH3
(ii)H 2O2 /OD

D OH

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CH2 N 2 /h
(C)  

HgSO4
(D) CH3 – C  C – Ph 
H 2SO4 /H 2O
 CH3 CH2 C Ph
O
Ans. (A, B, C)
10. Which of the following are correct :

1. O 3
(A) 2. Zn,H2O OHC – CH2CH2CH2 – CHO
H H
O
C6H5C OOH
(B) CH 2Cl 2 H H
H H O

KMnO4
H H
(C) cold dilute solution
H H
OH OH
O O
KMnO 4
(D) OH , heat
O CCH2CH2CH2C O
H H
Ans. (A, B, C, D)
11 Select correct statement :
(A) Methane cannot be prepared by catalytic hydrogenation of alkene
(B) Al isomers of the formula C6H14 can be prepared by catalytic hydrogenation of alkene
(C) All isomers of the formula C5H12 can be prepared by catalytic hydrogenation of alkene
D H2
(D) Ni product obtained show no optical rotation
D
Ans. (A, B, D)

12. Which of following reaction product is Diastereomer.

CHO
Br2 (i)NaCN
(A) CH3 (B) D H
CCl4 (ii)H+
CH3

CH3 CH3
HBr HCl
(C) C=C
CCl 4
(D) CH3 CH CH=CH Ph peroxide
H H Et
Ans. (A, B, D)

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13. Which of the following produce aromatic product.

Red hot
(A) Me – C  CH Fe tube
(B) C6H14

NH2
CHCl 3
CHO
(C) KOH (D) + 

NH2 CHO

Ans. (A, B, C)
14. Which of the following represent correct product formation.
O
O CH2SH
Zn - Hg
(A) CH2SH (B)
N HCl N
H2 Raney Ni/
H H
O
O
NH2-NH2
(C) Red P (D) EtOK
Hl (excess) N N
H H
Ans. (A, C, D)
15. Suitable reagent(s) to carry out following conversion is/are

O
N C CH3 N Et
CH3 CH3
CH2 SH
(A) /H2/Ni followed by OH (B) N2H4 /H2O2
CH2 SH
(C) N2H4 / EtONa (D) Zn / Hg / HCl
Ans. (A, C)

16. What are the possible intermediates in the following reaction ?

(1)Br2  CCl4
CH3  CH 2  CH  CH 2 
(2) NaNH2 / 
 CH3  CH 2  C  CH

(A) CH3 CH2 CH CH2Br (B) CH3CH2 CH CHBr

Br

(C) CH3 CH2 C CH2 (D) CH3  CH CH  CH  Br
Br
Ans. (A, B, C)

17. When is reacted with Br2 (1-equivalent) would give ;

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Br
Br Br Br
Br Br Br
(A) (B) (C) (D)
Br

Ans. (A, B)

18. Which of the following reactions are correct ?

 H Br H
Br2 (i)C6 H5COOH CH2 Cl2
(A) 
CCl4 (B) 
(ii)OH /H O

2

Br H H

Me
Me
(C)
H  /H 2O

 (D) Me
H  /H 2 O
  Me Me H

Me H Me
Me
Ans. (A, B, C)
19. The reagents used to convert (E)-2,3-dibromo-2-butene to 2-butyne

H3C Br
C C  CH3 – C  C – CH3
Br CH3

(A) Zn dust /  (B) Mg,  (C) NaI/ Acetone / (D) Alc. KOH
Ans. (A, B, C)

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Misc. Exercise
Subjective

H D

H D
NaOH
1. (A) H 
Alcoholic
 A . Write the structure of A.
D H
Br

CH3

CH3  OH
(B) N 

 B. Write the structure of major product A.
 CH3

2. One of the constituent of turpentine is -pinene havinig molecular formula C10H16. The following scheme give
reaction of  - pinene. Determine the structure of -pinene & of the reaction products A through E.

E(C10H18O2) A(C10H16Br2)
H2O Br2/CCl4
PhCO3H Br2 + H2O
C10 H16 O(D) -pinene B(C10H17OBr)
OsO4 (i) O3 (i) H2SO4
H2O (ii) Me2S (ii) 
F
H C(C10H15Br)
OO

3. Propose structures for intermediates & products A to K

Mg, ether 1.CH3(CH2)3 CHO

1 bromobutane D + E
2. H3O
KOH, H2O H2SO4 , 

A F
O3
1.
Na e 2S Br2
EtBr nPr CHO . M
+ 2
B C G
nBuCHO
fused KOH
followed by NaNH2
H

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4. Identify the following (A to D),

Me
E + D + C O + CH3CO2 H
Me
Racemic Mixture

KMnO4 (hot)

C11H20 Lindlar's C11H18 Li/EtNH2 4 ethyl 2, 4 dimethyl

B Catalyst A 2, 5-heptadiene
Optically
active
O3/H2O
Me
+ C O + CH3CO2H
C6H10O4 Me
Optically inactive
C

5. What will be the product in the following reaction

1.NaNH 2 (3equiv.) NH 3
+ Br2 
 A  2.CH 3I
B

6. Write the structural formula of limonene from the following observation :

(A) Limonene when treated with excess H2 & Pt catalyst, the product formed is 1-isopropyl-4-methylcyclohexane
(B) When it is treated with O3 & then Zn/H2O the products of the reaction are HCHO & following compound

O O

7. There are six different alkene A, B,C, D, E and F. Each on addition of one mole of hydrogen gives G which has the
lowest molecular wt hydrocarbon containing only one asymmetric carbon atom. None of the above alkene give
acetone as a product on ozonolysis. Give the structure of A to F. Identify the alkenes that is likely to give a ketone
containing more than five carbon atoms on treatment with a warm conc. solution of alkaline KMnO4.
8. 3,3–dimethyl–1–butene and HI react to give two products, C6H13I. On reaction with alc. KOH one isomer, (I) gives
back 3, 3-dimethyl–1–butene the other (J) gives an alkene, that is reductively ozonized to only Me2C=O. Give the
structures of (I) and (J) and explain the formation of the later.

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9. Three isomeric alkenes A, B and C, C5H10 are hydrogenated to yield 2-methylbutane A and B gave the same 3° ROH
on oxymercuration demercuration. B and C give different 1° ROH’s on hydroboration-ixidation. Supply the struc-
tures of A, B & C.
10. Two isomeric alkyl bromides A and B (C5H11Br) yield the following results in the laboratory. A on treatment with
alcoholic KOH gives C and D (C5H10). C on ozonolysis gives formaldehyde and 2 methyl propanal. B on treatment
with alcoholic KOH gives only C (C5H10). Deduce the structures of A, B, C and D. Ignore the possibility of geometri-
cal and optical isomerism.
11. Give the structure of A, B and C.
(A) A (C4H8) which adds on HBr in the presence and in the absence of peroxide to give the same product C4H9Br.
(B) B (C4H8) which when treated with H2SO4/ H2O give (C4H10O) which cannot be resolved into optical isomers.
(C) C (C6H12), an optically active hydrocarbon on catalytic hydrogenation gives an optically inactive compound
C6H14.
12. An alkylhalide, X, of formula C6H13Br on treatment with potassium tertiary butoxide gives two isomeric alkenes Y
and Z (C6H12). Both alkenes on hydrogenation gives 2,3–dimethylbutane predict the structures of X, Y and Z.
13. Compound A (C6H12) is treated with Br2 to form compound B (C6H12Br2). On treating B with alcoholic KOH followed
by NaNH2 the compound C (C6H10) is formed. C on treatment with H2/Pt forms 2-methylpentane. The compound ‘C’
does not react with ammonical Cu2Cl2 or AgNO3. When A is treated with cold KMnO4 solution, a diol D is formed
which gives two acids E and F when heated with KMnO4 solution. Compound E is found to be ethanoic acid.
Deduce the structures from A to F.
14. A organic compound A having carbon and hydrogen, adds one mole of H2 in presence of Pt catalyst to form normal
hexane. On vigrous oxidation with KMnO4, it gives only one simple carboxylic acid containing 3 carbon atoms.
Assign the structure to A.
15. Give the product of

BH3 H 2O 2

THF
 A 
OH 
B

C2H5 C2H5
16. C C 1.CF3 CO 3 H
   A  B . What are A and B ?
2.H O / H 
H H 2

17. What are A to K for the following reactions

(i) PhC  CH + CH3MgX  ArCH2 Cl

 A  Li/NH3
 B  C
h Alcoholic Cold dil. KMnO4 hot KMnO4
(ii) PhCH2CH2CH3 + Br2   D 
KOH
 E(Major)    F  G

H
CH3 l
(iii)   (iv)  
Me Me H3C OH OH

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Me

HBr
(v) CF3 – CH = CH2  NBS
 J (vi)  K

Me Me

18. A chloro compound (A) showed the following properties :

(i) Decolourized bromine in CCl4
(ii) Absorbed hydrogen catalytically
(iii) Gave a precipitate with ammonical cuprous chloride
(iv) When vaporised 1.49 g of (A) gave 448 mL of vapours at STP.
Identify (A) and write down the equations of reactions.

Cl
KOH
19. Number of cyclic product(s) formed + HC F
Br

20. It required 0.7 g of a hydrocarbon (A) to react completely with Br2 (2.0 g) and form a non resolvable product. On
treatment of (A) with HBr it yielded monobromo alkane (B). The same compoud (B) was obtained when (A) was
treated with HBr in presence of peroxide. Write down the structural formula of (A) and (B) and explain the reactions
involved. Total dibromoderivative possible for (A) are :
21. Give stability order in the following pairs
I II I II

CH2 CH2

(a) (b)


 
(c) CH 2  N H 2 CH 2  NH 2 (d)

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Match the Column

22. Match the column I and II.
Column (I) Column (II)
Reaction Type of Reaction

(A) (p) Meso compound

H2
Ni
CH3

D2
(B) Pt (q) Diastereomers
CH3 CH3

CH2

(C) H2 (r) Racemic

Pt
CH3O

H2
(D) Pt (s) Optically inactive due to absence of chiral center
H H

23. Match the column

Column (I) Column (II)
Reaction Product

CH3 CH3
D
T
(A) (1) BD3:THF (p)
(2) CH3CO2T

CH3 CH3
D
H
(B) (1) BT3:THF (q)
(2) CH3CO2D

CH3 CH3
H
D
(C) (1) BD3:THF (r)
(2) CH3CO2H

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CH3 CH3
T D
(D) (1) BH3:THF (s)
(2) CH3CO2D

24. Match the column.

Column (I) Column (II)
Wurtz Reaction Number of dimerization product
Na
(A) CH 3 Cl
dry ether (p) 5

Na
(B) CH3 Cl + CH 3 CH2 Cl dry ether (q) 6

CH3 Cl + CH3 CH2 Cl

(C) + CH3 CH2 CH2 Cl Na (r) 3
dry ether

H2C = CH CH= CH CH2 Cl

(D) Na (s) 1
+ CH3 CH2 Cl dry ether

25. Match the column I with column II with column III (Matrix)
Column-I Column-II Column-III
Reaction Nature of product formed Number of chiral center present in product,
(Consider only one isomer in case of racemic
mixture or Diastereomer)

Br2
(A) CCl4 (p) Racemic mixture (w) 0
H
CH3

Br2
(B) CCl4 (q) Meso (x) 1
H
CH3

Br2
(C) CCl4 (r) Diastereomer (y) 2
CH3

CH3 H Br2
(D) C C CCl4 (s) Vicinal dihalide (z) 3
H CH3

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26. Match the colum I and II.

Column (I) Column (II)
Reaction Product

OH
(1) OsO4
(A) (2) NaOH, H2O (p)

(1) BH3/ ether Cl

(B) (2) H2O2, NaOH, H2O (q) OH

OH
Cl2, H2O
(C) (r) OH

Cl
Cl2 / CCl4
(D) (s) Cl

27. Match the column I and II :

Column (I) Columni (II)
Conversion Reagent
CH3
Br

(A) Br (p) SO2Cl2/ h (2 equivalent)

CH3 CH2-Cl

(B) Cl (q) NBS (2 equivalent)

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CH3 Br

Cl
(C) (r) NBS then SO2Cl2/ h

CH3 CH2-Cl

Br
(D) (s)SO2Cl2/ h then NBS

28. Match the column I with Column II

Column I Column II
electrolysis
(A) RCOONa   R–R (P) Correy - House reaction
NaOH,CaO
(B) R – CH2 –COOH 
 R – CH3 (Q) Kolbe electrolysis

(i )AgNO3
(C) RCOOH 
(ii)Cl2 / 
 R  Cl (R) Oakwood degradation / Soda lime process
(D) R’ – X + R2CuLi  R–R’ (S) Hunsdiecker reaction

29. Match the column I with Column II

Column I Column II
(i)BH 3 / THF
(A) CH3 C CH2 
(ii)H 2O 2 /OH
 (P) CH3 – CH2 – CH = CH2
CH3
(i)Hg(OAc) 2 /HOH
(B) CH3 C CH2 
(ii) NaBH 4
 (Q) CH3 – CH = CH – CH3
CH3

Cl
CH3ONa/
(C) CH3 CH2 CH CH3   (R) CH3 CH CH2OH
CH3
Cl OH
(CH3 )3 CONa
(D) CH3 CH2 CH CH3  
 (S) CH3 C CH3
CH3

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Comprehension
Paragraph (30 to 32)
4-Isomeric alkenes P, Q, R, S with molecular formula C4H8 has following heat of combution data

Head of Combination
S
Q
P R

30. Identify alkene give meso product on reaction with Br2/CCl4 ?

(A) P (B) Q (C) R (D) S
31. Identify alkene give fastest reaction with HBr / CCl4 ?
(A) P (B) Q (C) R (D) S
32. Identify alkene give racemic mixture on reaction with Br2/CCl4 ?
(A) Q (B) R (C) P (D) All of these

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ISOMERSIM

Single Choice Questions

1. Which of the following cyclopentane derivative is optically inactive ?

OH H CH3 CH3 H CH3

(A) (B) OH H (C) (D)

H OH H H OH H
H OH
CH3

(E) H
H

CH3

Ans. (C)

2. Which is the most stable conformer along the 2, 3 C – C bond axis of the compound ?

H3C F
H H
H3C CH3

F F CH3 H
H CH3 H CH3 H H H3C F
(A) (B) H CH3 (C) F (D) H3C H
CH3
CH3 H H3C CH3 CH3 H 3C

Ans. (B)

3. How many meso isomers of C4H8Cl2 will be ?

(A) 0 (B) 1 (C) 2 (D) 3

Ans. (B)

4. The stable form of trans-1, 4–dimethylcyclohexane is represented as :

CH3
CH3

(A) (B)
CH3 CH3

CH3

(C) CH3 (D)

H3C
CH3

Ans. (C)

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5. The following molecule is fluorometholone, a steroidal anti-inflammatory agent. How may stereogenic centers does it

contain ?
O CH3
H3C OH
HO
H3C H
F H Fluorometholone
O
CH3
(A) 5 (B) 6 (C) 7 (D) 8

Ans. (D)

6. Among the following, the optically inactive compound is :

O
N S
CH3
(A) H3CH2C (B)
H 3C

H3C
CH3
(C) (D)

H
Ans. (A)
OH COOH
7. Which of the following molecules is (are) chiral ?

Cl H CH3 H
(I) C (II) (III)
H Br CH(CH3)2

H H3C H3C
H H
O
(IV) (V) (VI)

H O O O

(A) I and II (B) III and IV (C) II, IV and VI (D) I, II, III and VI

Ans. (D)

8. How are the following compounds related ?

H3C Br CH3
Br
Br
H Br H
(A) Diastereomers (B) Enantiomers (C) Meso compounds (D) Non Identical

Ans. (D)

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9. Among the following , the Newmann projections of meso-2, 3-butanediol are : -

Me Me Me Me
H OH H OH HO Me Me H

HO H H OH HO H H OH
Me Me H OH
P Q R S

(A) P, Q (B) P, R (C) R, S (D) Q, S

Ans. (B)

10. Which of the following pairs of compounds is a pair of enantiomers ?

Br Br

(A) (B)
Cl Cl
Cl Cl

(C) (D)
Cl Cl Cl Cl
Ans. (B)

11. The following pair of compounds is best described as :

(A) Identical (B) Diastereomers (C) Enantiomers (D) None of the above

Ans. (D)

12. Which is the following compounds is most stable ?

(A) (B) (C) (D)

Ans. (D)

13. The following compounds differ in respect of :

HO O OH HO O OH

HO OH HO OH
OH OH
(A) Their chemical and physical properties
(B) Nothing
(C) The direction in which they rotate plane of polarized light
(D) Their interactions with molecules

Ans. (C)

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14. Indicate whether each of the following pairs identical, or ?

F
H H Cl
Br H Cl CH2CH3 H CH2CH3
H3C CH2Br
(I) (II) CH3 CH3
H CH3 F Cl Cl
H H
H
CH3 CH3
H Br Br H
(III)
CH3 H H CH3
Br Br
I II III

(A) Enantiomers Diastereomers Enantiomers

(B) Identical Enantiomers Enantiomers

(C) Enantiomers Diastereomers Identical

(D) Enantiomers Identical Identical

Ans. (C)

15. Which of the following compounds has a zero dipole moment ?

Cl
Cl
Cl Cl Cl
(A) (B) (C) (D)
Cl Cl
Cl Cl

Ans. (D)

16. How many isomers are possible for the following molecule ?

H
CHCH= CHCOOH
H3C

(A) 1 (B) 2 (C) 3 (D) 4

Ans. (D)

17. Which equilibrium is not rapid at room temperature ?

Br Me
Cl
(A) (B)
Cl Me Cl Br
Me Cl Me

H CH3 H3C CH3

(C) (D)
H3C H H H
H H H H

Ans. (B)
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18. Which of the structures given below are chiral ?

H CH2OH
CH3 O CH2OH
HO H
Cl
(I) O O (II) Cl H (III) HO H
H HO H
CH3 O CH2OH CHO
H
Fischer projections

CH2OH
HO H
(IV) HO H (V)
HO H
CH2OH O

(A) I, II, III (B) II, III, V (C) II, III (D) I, II

Ans. (B)

19. A naturally occurring substance has the constitution shown below. How many may have this constitution?

O
HO CH2OH

HO CH CHCH CHCH2CH2CH3

(A) 2 (B) 8 (C) 16 (D) 64

Ans. (D)

20. How many different stereoisomers are possible for the following compound ?
H
ClHC=HC–C–CH=CHCl
Cl
(A) 1 (B) 2 (C) 3 (D) 4

Ans. (D)

21. Which of the following has unstable enol form ?

O O O
O O O
(A) (B) (C) (D)

O
Ans. (C)

22. Total number of stereoisomers possible for following compound is :

CH CH — CH2CH3

CH CH2
(A) 8 (B) 16 (C) 32 (D) 64

Ans. (A)
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CH2 - OH CH2 - OH CHO

H OH HO H H OH
HO H HO H H CH2OH
23.
CHO CHO OH
(a) (b) (c)

(D) & (L) Configuration of above carbohydrate is :

(A) L, L, D (B) L, D, L (C) L, L, L (D) L, D, D

Ans. (B)

O
O O
24.
O O
O
(I) (II) (III)

Among the given structure which can exhibit tautomerism ?

(A) I only (B) II only (C) III only (D) none of these

Ans. (B)

OH O OH

25.

(I) (II) (III)

Correct stability order of the given tautomers is :

(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I

Ans. (C)

26.

How many geometrical isomers are possible for the above compound ?

(A) 3 (B) 4 (C) 6 (D) 8

Ans. (B)

H l1 H
27. C=C=C
H l2 H

Choose the correct relation between l1 and l2 ?

(A) l1 = l2 (B) l1 > l2 (C) l1 < l2 (D) l2 = 2l1

Ans. (A)

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H l1 H
28. C=C=C=C
H l2 H

Choose the correct relation between l1 and l2 ?

(A) l1 = l2 (B) l1 > l2 (C) l1 < l2 (D) l2 = 2l1

Ans. (C)

29. CH3 – CH = C – C = CH – CH2

Br Br
How many geometrical isomers of this compound are possible ?
(A) 2 (B) 3 (C) 4 (D) 6
Ans. (B)
30. Which of the following is correct for the given compound ?

O O

(A) It possess centre of symmetry (B) It possess C4 axis of symmetry

(C) It possess plane of symmetry (D) Compound is chiral

Ans. (C)

31. How many stereocenters does latomoxef (an oxacephem antibiotic) have ?

HO O
N N O
S N
N N O
NH OH
O
O

(A) 2 (B) 3 (C) 4 OH (D) 5

Ans. (B)

32. Which molecule is (R, Z)-7-methoxy-2,7-dimethyl-4-propylnona-1,4-diene ?

H3CO OCH3
(A) (B)

H3CO OCH3
(C) (D)

Ans. (A)

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33. Choose the correct order that has the following compounds correctly arranged with respect to thermodynamic stability:

CH3

(i) CH3 (ii) H3C CH3 (iii)

CH3 CH3

(A) ii < i < iii (B) i < ii < ii (C) i < iii < i (D) iii < i < ii

Ans. (D)

34. Which of the structures below is a diastereomer of A ?

H H

HO

CH3

CH3 CH3 H
H
(I) (II) (III) OH
OH HO
H H
H H CH3

CH3 H
H
(IV) OH (V) HO
H
H
CH3

(A) I (B) III (C) II and IV (D) IV and V

Ans. (D)

35. Given compound shows which type of isomerism ?

O O
S–O and S–O
O O

(A) Chian isomerism (B) Positional isomerism

(C) Metamersim (D) Functional group isomerism

Ans. (C)

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36. Which of the following pairs of compound is/are identical ?

Cl CH3 CH3 I
H I H
CH3 Cl H H CH3
(A) (B) Cl
H CH3 Cl H Cl I
Cl CH3 I H H

Br H H Br
F H F Br H H H Cl
(C) Br H (D)
F Br Br I H I
F H Cl H

Ans. (C)

37. The two structures I and II represent :

CH3 CH3
H H H H
(I) (II)
H3C CH3 H3C H
H CH3

(A) Conformational isomers (B) Stereoisomers

(C) Constitutional isomers (D) Identical

Ans. (C)

38. The possible number of alkynes with the formula C5H8 is :

(A) 2 (B) 3 (C) 4 (D) 5

Ans. (B)

39. How many isomers of C5H11OH will be primary alcohols :

(A) 2 (B) 3 (C) 4 (D) 5

Ans. (C)

40. Number of isomeric forms of C7H9N having benzene ring will be :

(A) 7 (B) 6 (C) 5 (D) 4

Ans. (C)

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ETOOSINDIA F.T.R. BY N.J. SIR
INDIA’S NO. 1 ONLINE COACHING

41. Keto-enol tautomersim is observed in :

O O
(A) C6H 5—C—H (B) C6H 5—C—CH3

O O CH3
(C) C6H5—C—C6H5 (D) C6H5—C—C—C6H5

CH3

Ans. (B)

42. The value of equilibrium constant (K) for the following equilibrium

H H H
H3C e a CH3
C e H H3C
C C
a CH3
H3C CH3
CH3 C H3C
H3C CH3 CH3
CH3
Chair Twist boat

(A) K = 1 (B) K > 1 (C) K < 1 (D) Cannot relate

Ans. (B)

43. Which of the following compounds are chiral ?

O H 3C Cl
C–NH
C=C=C Cl
(I) (II) (III)

NH–C
Cl H CH3
O
Cl

Cl H
Cl H O
C
(IV) (V)
NH
O O
C
O

(A) I , II , III , IV (B) II , III , V (C) I , II , III , V (D) I , IV , V

Ans. (B)

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ETOOSINDIA F.T.R. BY N.J. SIR
INDIA’S NO. 1 ONLINE COACHING

44. The conformation of the following compound is :

Et
Me

CMe3
Me3C
Me
Me3C
(A) (B) Me
Et Et

(C) Me3C (D) Et

Me CMe3
Et
Ans. (B) Me
45. Calculate the total number of geometrical isomers for the following compound :

(A) 2 (B) 4 (C) 8 (D) 16

Ans. (B)

46. Identify the relationship between the following pairs of compound :

H H H
H H
and
H H
H H H

(A) Positional isomers (B) Geometrical isomers

(C) Functional isomers (D) Identical compounds

Ans. (B)

47. Identify the pair of diastereoisomers

Cl Cl
(A) (B)
Cl Cl Cl Cl

Cl Cl
(C) (D)

Ans. (A)

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ETOOSINDIA F.T.R. BY N.J. SIR
INDIA’S NO. 1 ONLINE COACHING

48. Identify the pair of diastereoisomers :

O O
(A) (B)
O O

Cl Cl
(C) (D)
Br Cl Cl Br

Ans. (A)

49. Identify the pair of diastereoisomers :

(A) (B)

Cl Cl

(C) (D)
Cl Cl
Ans. (A)

H
H Y
50. Newmann projection representation of CH3–CH2–CH–Et about C2–C3 is
X H
CH3 Me

Then X & Y are respectively :

(A) Me, Et (B) H, Et (C) Et, H (D) Et, Me

Ans. (A)
51. The correct stability order of the following species is :-

H H Me
H Me
Me
Me H Me
(a) Me
H H
(c)
(b)
(A) c < a < b (B) c = b < a (C) c < a = b (D) a = b = c
Ans. (C)
52. How many H(Hydrogens) will be replaced by D (Deuterium) in given compound when it is kept in mild

basic medium for a long time.

O –
OD / DOD
Deuterium exchanged product [3]

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ETOOSINDIA F.T.R. BY N.J. SIR
INDIA’S NO. 1 ONLINE COACHING

(A) 3 (B) 6 (C) 10 (D) 8

Ans. (C)

53. Which one of the following will not show geometrical isomerism :

Et Me
O
(A) (B)

Me NH

NH O O
(C) (D)

Ans. (D)

54. Write the number of minimum carbon atoms required for chiral molecule in following compound.

(i) sp and sp3 (ii) sp and sp2 (iii) only sp2 (iv) sp2 and sp3

(A) 5,5,5,8 (B) 5,4,5,7 (C) 4,4,6,7 (D) 4,4,4,6

Ans. (C)

55. Select the correct statement.

(A) Boat form of cyclohexane has a C2 axis and three plane of symmetry

(B) In the threo isomer of PhCH(OH)CH(NR2) Ph the most stable conformer is one in which two Ph group are guache to

each other

(C) CH4 molecule has 4-POS present in the molecule.

(D) None

Ans. (B)

56. How many plane of symmetry are present in following compound :

(A) 0 (B) 1 (C) 2 (D) 3

Ans. (C)

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ETOOSINDIA F.T.R. BY N.J. SIR
INDIA’S NO. 1 ONLINE COACHING

57. A 1.20 gm sample of cocaine, [  ]D = – 16° was dissolved in 7.50 mL of chloroform and placed in a polarimeter tube

having path length of 5.00 cm. Calculate the observer rotation ?

(A) +1.3° (B) –2.6° (C) +2.6° (D) –1.3°

Ans. (D)

58. Compound showing geometrical isomerism :

A B C D E
(A) A only (B) B only (C) B & C (D) C & D

Ans. (C)

Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 15
Multiple Choice Exercise
1. Which of the following statement is/are correct :
(A) Cis 1,2-dichloroethene is relatively more stable than its trans form
(B) Trans cyclohexadecene is relatively more stable than its cis form
(C) Cis form of 1,3,5-trimethylchlohexane is relatively more stable than its trans form
(D) None of these

Ans. (A,B,C)

2. Which of the following is/are incorrect :

(A) CH3–CH2–CH2–CN and CH3–CH–CH3 are positional isomers

CN
(B) CH3–CH–O–CH3 and CH3–CH2–O–CH2–CH3 are positional isomers
CH3

O OH

(C) and are functional group isomers

O O HO OH
CH3
(D) CH3–C=CH2 and are ring chain isomers

Ans. (A,B,C)

3. Which will show geometrical isomerism :

Cl Cl
D D D D
T T
(A) H H (B) (C) (D)
H H

Ans. (A,B,C)
4. Which will show geometrical isomerism :
H3C
(A) CH3CH=NOH (B) (C) C=NOH (D) HO–N=N–OH
H3C
Ans. (A,B,D)
5. Select true statement(s) :

(A) Resonance effects bond length

(B) cis-1-bromo-1,2-difluoro ethene and Z-1 bromo-1,2-difluoro ethane are geometrical isomerism

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 O
COH
(C) In H2C most acidic H is connected directly to oxygen not on carbon
COH
O OH
OH OH
(D) Boiling point of is less than

Ans. (A,B,C,D)

6. Select the correct statement for the following species.

Me
Me Me
Me
(I) (II) (III) (IV)
Me Me
Me Me

(A) I & II are geometrical isomers (B) II & III are geometrical isomers

(C) III & IV are conformers (D) I & IV are conformers

Ans. (B,C)

7. Which of the following molecules, in pure from, is (are) unstable at room temperature ?

O O

(A) (B) (C) (D)

Ans. (B,C)

8. Which of the following molecule(s) show the plane of symmetry as well as axis of symmetry ?

Me
Cl
Br H
(A) Me (B)

H Br Me Cl

D D
Cl

(C) (D)

Cl
Cl

Ans. (B,D)

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9. The C3 axis of symmetry is present in which of the following compounds ?

H
Cl
H B H
N N
(A) B B (B) (C) (D)
H N H
H Cl Cl

Ans. (A,B,C,D)

10. Which of the following compounds are chiral ?

Br H H + H
(A) (B) N
C2H5–O–C C6H5
H Br

H H
C C C C C
O C
(C) (D)
C
H CH3 NO2 NO2
Ans. (A,B,C)
11. In which of the following case correct relationship is given ?

H3 C Br CH3
Br

(A) Enantiomers

H Br Br H

(B) Enantiomers
Br H H Br
H Br Br H

Br I Br I

(C) Diastereomers
HO CH3 HO CH3

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 (D) Cl Cl Enantiomers
Br Br

Ans. (B,C,D)
12. Identify amongst the following compounds having plane of symmetry, centre of symmetry and axis of symmetry :

Me Cl Cl H
Cl H Cl
Cl H Me Ph H H
(A) (B) (C) H (D) Ph
Cl Cl H
H H H Cl

Ans. (A,B)
13. Identify diastereo isomeric pairs :

COOH
COOH

(A) and

OH OH

(B) and

Cl Cl

(C) HO OH and HO OH

Cl Cl

Cl Cl
Cl Cl

(D) and

Me H
H Me
Ans. (A,B,C,D)

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14. Identify the optically active compound :

H Cl H
H Me H
H
(A) (B)
Me H H H
H Br H

Ph Cl
Br Cl
(C) (D)
Cl OH Ph H

Ans. (C,D)

15. Which of the following molecules is /are optically active ?

H 3C H3C
H H
H H
H OH H OH
(A) CH3 (B) H
H H
H CH3

H
H Br
(C) (D) Br Me
OH Me

Ans. (A,C,D)
16. Identify the structure of meso compounds :

D D Cl
CH3 H3C OH
CH3 CH3
H H D
Cl D
CH3
(A) D (B) (C) (D) T
H Me
D H D H3C OH
CH3

Ans. (A,B,C)
17. Identify the structure of meso compounds :

D H3C CH3
OH CH3 CH3
H CH3 H H OH
(A) (B)
CH3 (C) (D) Br D
H3C OH HO H Br D
D H
CH3 CH3
Ans. (B,D)

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18. Identify the structure of optically inactive compounds :

D Cl
CH3 HO OH CH3 HO OH
H D
(A) (B) (C) Cl (D)
D
H
D H
CH3

Ans. (A,B,D)

19. Identify the structure of identical compounds :

HH

(A) (B) (C) CH2 (D)

Cl Cl Cl Cl Cl Cl
Cl
Cl
Ans. (C,D)

20. Identify the pair of diastereoisomers :

O O
(A) (B)
O O

Cl Cl
(C) (D)

Ans. (C,D)
21. In which of the following reaction a racemic mixture will be formed.

N N
(A) H3C DCl (B) H3C HCl
H CH2CH3 
 H CH2CH3  

N N
(C) H3C CH2CH3
DCl
   (D) H3C D
HCl
CH2CH3  
D
Ans. (A, D)

22. Which of the following compounds will show tautomerism :

O
O O
(A) C–ND2 (B) O (C ) C (D)

N–OH
Ans. (A, D)

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Misceleneous Exercise
Statement Type Questions

F F

1. Statement-1 :

F F
(I) (II)

(I) and (II) are optically active molecules.

Statement-2 : Molecules containing plane of symmetry or centre of symmetry or both cannot be optically active.

(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1

(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for statement-1

(C) Statement-1 is false, statement-2 is true.

(D) Statement-1 is true, statement-2 is false.

2. Statement-1 : The enol form of O O is less stable.

O
Statement-2 : The enol form has opposite charge separation.

(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1

(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for statement-1

(C) Statement-1 is false, statement-2 is true

(D) Statement-1 is true, statement-2 is false.

H5C2 Cl H5C 2 Cl
3. Statement-1 : C=C and Br C=C are structural isomers.
H3C Br CH3
Statement-2 : The above mentioned compound can show geometrical isomerism.

(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.

(B) Statement-1 is true, statement-2 is true and statement-2 is NOT the correct explanation for statement-1

(C) Statement-1 is true, statement-2 is false.

(D) Statement-1 is false, statement-2 is true.

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Integer Type :

4. Number of compound having COOH groups ?

(i) Picric acid (ii) Citric acid (iii) Barbituric acid (iv) Carblic acid

(v) Salicyclic acid (vi) Cinnammic acid (vii) Aspirin (viii) Salicylaldehyde

(ix) Ascorbic acid (x) Benzene sulphonic acid

5. Find relationship between following pairs.

Me Me F Cl
H OH Me OH Cl Br F Br
(a) H OH & HO H (b) Cl Br & Br I
H OH H Me
I Cl
Me OH
SH SH OH

(c) CH3CH2CH2–CHO & CH–CH–CH (d) OH &

3 3

CHO
Br Br Br OH
H
Br
(e) & (f) OH & D
D H
T T
6. How many total number of structural isomers of C4H6Cl2 are possible having 3-membered cyclic structures.

7. How many compounds of formula C5H10 are incapable of showing stereoisomerism.

8. (a) How many plane of symmetry are present in prismane (C6H6) ?

(B) How many chiral centres are present in the following compound?

(C) Minimum carbon atoms required for an hydrocarbon alkane to show optical isomerism.

9. Among following pairs which will require lower heat of activation for cis-trans inter conversion :

(a) Me–CH=CH–Me & Me–CH=CH–OMe

(b) CH=CH & CH=CH NO2

(c) CH=CH & CH=CH OMe

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 (d) O2N CH=CH NO2 & O2N CH=CH OMe

(e) Me–O–C–CH=CH–C–O–Me & Me–O–C–CH=CH–O–C–Me

O O O O
Me
Me
(f) &
Me Me
Me Me
Me
(h) &

Me

10. Calculate total number of geometrical isomers in following compound :

(i) CH3–CH=CH–CH=CH–CH=CH–CH3

(ii) CH2=C=CH–CH2–CH=C=C=CH–Me

Me
(iii) (iv) (v) Br–CH=C=C=CH–CH=CH–Br
D
11. How many total number of structural isomers of C4H6Cl2 are possible having cyclic structures.

12. What will be the effect on dipole moment of following compounds, when temperature is increased.

(a) cis-1,2-dichloro ethene

(b) 1,2-dichloro ethane

Explain with suitable explanation in each case.

13. How many stereoisomers are possible for the following compound ?
O
N
NH
N N NH2
HO O

O
HO P O
OH

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14. How many compounds are optically active ?

N N N N
(a) (b)
N

COOH
Br
(c) (d) Br (e)
Br
Br COOH

NO2 Cl Cl
O
(f) (g) (h)
O
Br Br NO2

(i) (j) (k) () Br

I

Cl

15. How many compounds are optically inactive ?

O O
(a) (b) (c) (d)
O

O O NH
(e) (f) (g) (h)
HN O O

O HN
(i) (j) (k) ()
O NH

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 Cl Cl
(m) (n) (o) (p)

Cl Cl

O
(q)

16. How many geometrical isomers are possible for the following compound ?

H3C CH3

H3C CH3

17. How many geometrical isomers are possible for the following compound ?

Ph COOH

HOOC Ph

18. How many stereoisomers are possible for the following compound ?

CH3
Cl Br
Cl Br
H3C CH3
Br Cl
Cl Br
CH3

19. What is the lowest molecular weight of a saturated cyclic hydrocarbon which has all its carbon atoms different.
20. Calculate molecular weight of the lowest alkane containing a sequence of 1°, 2°, 3° and 4° carbon atoms.
21. For the conformational isomers, the net dipole moment is µobs =  µixi where µobs = observed dipole moment of the
compound µi = dipole moment of the stable conformational isomers xi = mole fraction of stable conformers for the
compound Cl – CH2 – CH2 – Cl, if Xanti = 0.7 and µobs = 2D, then find µgauche

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Comprehension Type :

Paragraph for Q.No. 22 to 24

OH
H
H OH Ph
H OPh
(I) (II) (III) (IV) H
H Br H Ph H Br
Br OH
Br Ph

H
Ph OH
HO H Br
(V) (VI)
H Br Ph
Ph
22. Correct statement is

(A) I and III are enantiomers (B) III and V are diastereomers

(C) I and IV are identical (D) I and VI are diastereomers

23. Diastereomeric pair is :

(A) I and II (B) I and VI (C) II and V (D) III and VI

24. If Br is attached in place of –OH group in structure “V” (with same stereochemistry) than resultant structure is :

(A) Meso

(B) Threo

(C) Structure has odd degree of unstaturation

(D) Structure is identical to (I) compound

Paragraph - 2 (Q. 25 to Q. 29)
Observe the following compound ‘P’ and given answer

(1)
H I
(4)
O (6)
D
H
(5)
D
(3)
(2)D Br
(P)

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25. The enol form of ‘P’ is formed by ionization at position :
(A) 1 (B) 2 (C) 3 (D) 4
26. A stable carbocation is formed by ionisation at position :
(A) 3 (B) 1 (C) 4 (D) 2
27. The ozonolysis product of P, (by using reductive ozonolysis) gives negative test with
(A) 2, 4-Dinitrophenyl hydrazine (B) Ammonical silver nitrate
(C) I2 / OH– (Iodoform test) (C) Ammonical cuprous chloride
28. The carbocation of ‘P’ obtained by ionisation of X– (halide ion), can be observed at position/s :
(A) 3, 5 (B) 3, 6 (C) 5, 6 (D) 4, 5
29. The total number of chiral centres in ‘P’ is
(A) 1 (B) 2 (C) 3 (D) 4
Match the Column
30. Match the column :
Column - I Column -I I

CH3 H
H CH3OH H3C CH3NH2
(A) and (p) Structural isomers
NH3 OH

CH3 Cl
H Cl H CH3
(B) and (q) Identical
Et Et

CH3 H
H OH H3C Et
(C) and (r) Enantiomers
Et OH

H5C2 H5C2
(D) and (s) Diasteromers
OH H H OH
31. Match List - I, List - II & List - III :
List - I List - II List - III

CH3 H CH3
Br H HO H
H C C
(A) HO (1) (i) (2R, 3R)
CH3 CH3 Br

CH3 H
CH3
HO H
Br C C OH
(B) Br H (2) (ii) (2S, 3S)
CH3 CH3
H

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 CH3 H
CH3
H OH
H HO C C Br
(C) Br (3) (iii) (2S, 3R)
CH3
CH3 H

CH3 H
CH3
HO H Br OH
Br C C
(D) H (4) (iv) (2R, 3S)
CH3 H CH3

32. Match the Column (I) and (II)

Column (I) Column (II)
Molecules Relationship

Cl Cl
(a) and p Identical
CH3 CH3

Cl Cl
(b) and q Enantiometer
CH3 CH3

Cl CH3
(c) and r Diastereomer
CH3 Cl

Cl Cl
(d) and s Structural Isomerism
CH3
CH3
33. Match the Column (I), (II) and (III). Matrix
Column (I) Column II Column III
Property Molecules No. of Chiral Centre

CH3 CHDCl
C C
(a) (p) Optically active (w) 0
H H

CH3
(b) (q) Optically inactive (x) 1
CH3

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 O

(c) CH3 N HCl (r) Plane of symmetry (y) 2
Et

H H
(d) (s) Centre of symmetry (z) 3
Cl Cl

34. Match the Column (I) and (II). (Matrix)

Column I Column II
Molecule Property

Me
H

(a) (p) Meso compound

Me
H

(b) (q) Achiral

H
Me

Me
H

(c) H (r) Chiral compound

Me

Me
H

(d) Me (s) Compound will show geometrical isomerism

Me
H
H

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