C HE M IS T RY

WB-JEE
CHEMISTRY MASTER
QUESTION BANK

ORGANIC CHEMISTRY
IUPAC NOMENCLATURE, GOC & ISOMERISM
1. (I) O2N CO2CH3

(II) MeO CO2CH3

(III) Me CO2CH3

For the above three esters, the order of rates of alkaline hydrolysis is
(A) I > II > III (B) II > III > I (C) I > III > II (D) III > I > II

2. The correct order of acidity for the following compounds is:

OH OH OH COOH

NO2
NO2 CH3 OCH3
(I) (II) (III) (IV)
(A) II < IV < III < I (B) II < III < I < IV (C) II < III < IV < I (D) III < II < I < IV

3. For the following carbocations, the correct order of stability is

(I) ⊕CH2–COCH3 (II) ⊕CH2–OCH3 (III) ⊕CH2–CH3
(A) III < II < I (B) II < I < III (C) I < II < III (D) I < III < II

4. The total number of alkyl bromides (including stereoisomers) formed in the reaction
Me3C–CH=CH2 + HBr → will be
(A) 1 (B) 2 (C) 3 (D) No bromide forms

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5. Which of the following compound is asymmetric ?
Cl Cl Cl Cl
Br Br

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

Cl Br Cl Br

6. The compound, which evolves carbon dioxide on treatment with aqueous solution of sodium
bicarbonate at 25°C is
(A) C6H5OH (B) CH3COCl (C) CH3CONH2 (D) CH3COOC2H5

7. The indicated atom is not a nucleophilic site in

(A) BH−4 (B) CH3MgI (C) CH3OH (D) CH3 NH2
↑ ↑ ↑ ↑

8. The molecule/molecules that has/have delocalised lone pair(s) of electrons is/are

O O N
(I) OCH3 (II) H C C
H3C CH2 3 CH2
OCH3
(III) (IV) CH3CH=CHCH2NHCH3

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

9. The conformations of n-butane, commonly known as eclipsed, gauche and anti-conformations

can be interconverted by
(A) rotation around C—H bond of a methyl group
(B) rotation around C—H bond of a methylene group
(C) rotation around C1-C2 linkage
(D) rotation around C2-C3 linkage

10. The compound(s), capable of producing achiral compound on heating at 100°C is are
Me
Et CH2COOH Me
Et CH2CO2H

(A) HO2C CO2H (B)

Me HO2C CO2H
Me H
Et CO2H Et CO2H

(C) (D)
O Me O Me

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11. The ease of hydrolysis in the compounds CH3COCl(I), CH3–CO–O–COCH3(II),
CH3COOC2H5(III) and CH3CONH2 (IV) is of the order
(A) I > II > III > IV (B) IV > III > II > I (C) I > II > IV > III (D) II > I > IV > III

12. The correct order of reactivity for the addition reaction of the following carbonyl compounds
with ethylmagnesium iodide is
H H3C H (CH3)3C
C=O C=O C=O C=O
H H3C H3C (CH3)3C
(I) (II) (III) (IV)
(A) I > III > II > IV (B) IV > III > II > I (C) I > II > IV > III (D) III > II > I > IV

13. Among Me3N, C5H5N and MeCN (Me = methyl group) the electronegativity of N is in the order
(A) MeCN > C5H5N > Me3N (B) C5H5N > Me3N > MeCN
(C) Me3N > MeCN > C5H5N (D) Electronegativity same in all

14. In the IUPAC system, PhCH2CH2CO2H is named as

(A) 3-phenylpropanoic acid (B) benzylacetic acid
(C) carboxyethylbenzene (D) 2-phenylpropanoic acid

15. The correct order of acid strengths of benzoic acid (X), peroxybenzoic acid (Y) and
p-nitrobenzoic acid (Z) is
(A) Y > Z > X (B) Z > Y > X (C) Z > X > Y (D) Y > X > Z

16. The IUPAC name of the following molecule is

Me Me Me

Me
(A) 5, 6-dimethylhept-2-ene (B) 2, 3-dimethylhept-5-ene
(C) 5, 6-dimethylhept-2-ene (D) 5-iso-propylhex-2-ene

17. The correct order of decreasing H—C—H angle in the following molecule is
H H H H
H H H H
(I) (II) (III)
(A) I > II > III (B) II > I > III (C) III > II > I (D) I > III > II

18. Among the following structures the one which is not a resonating structure of others is
–
O O O O
Me – Me
O Me O Me
(I) (II)

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 –
O O O O
Me Me
O Me O –
(III) (IV)
(A) I (B) II (C) III (D) IV

19. The compound that will have a permanent dipole moment among the following is
H Cl Cl H Cl Cl
Br Br
H Cl H Cl Cl Cl
(I) (II) (III) (IV)
(A) I (B) II (C) III (D) IV

20. The correct order of decreasing length of the bond as indicated by the arrow in the following
structures is

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

21. The correct statement regarding the following compounds is

OH OH OH

OH OH OH
(I) (II) (III)
(A) all three compounds are chiral (B) only I and II are chiral
(C) I and III are diastereomers (D) only I and III are chiral

22. The most likely protonation site in the following molecule is

4
3
Me 1 5

Me 2
6
8 7

(A) C-1 (B) C-2 (C) C-3 (D) C-6

23. The order of decreasing ease of abstraction of hydrogen atoms in the following molecule
Ha Me
Hb

Hc
(A) Ha > Hb > Hc (B) Ha > Hc > Hb (C) Hb > Ha > Hc (D) Hc > Hb > Ha

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24. The correct order of basicity of the following compounds is

NH2 NH
1 2

NH2 NH2

NH H2N NH
3 4
(A) 1 < 2 < 3 < 4 (B) 1 < 2 < 4 < 3 (C) 2 < 1 < 3 < 4 (D) 4 < 3 < 2 < 1

25. From the following compounds, choose the one which is not aromatic.

(A) ⊕ (B) (C) (D) Me2N CH3

26. Chosse the correct statement(s) among the following.

H3C H H CH3
(A) C=C and C=C are enantiomers
H CH3 H3C H
(B) CH3CHO on reaction with HCN gives racemic mixture
C2H5 C2H5

(C) CH3 – C – H and H – C – OH are enantiomers

OH CH3
(D) CH3 – CH = NOH shows geometrical isomerism

27. In the following compound, the number of sp-hybridised carbons are

CH2 = C = CH – CH – C ≡ CH

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

28. In a mixture, two enantiomers are found to be present in 85% and 15% respectively. The
enantimoeric excess (ee) is
(A) 85% (B) 15% (C) 70% (D) 60%

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29. The total number of aromatic species generated in the following reactions is

THF
(i) Cl + SbCl5 (ii) + Sodium metal

Br H NH2

+ H2O HNO2
(iii) (iv)

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

MIXED REACTIONS
Θ
30. Ph—CDO 
50%aq.NaOH
Warm
→ Ph— COOH + an alcohol. This alcohol is
(A) Ph–CHD–OH (B) Ph–CHD–OD (C) Ph–CD2–OH (D) Ph–CD2–OD

31. The reduction product of ethyl 3-oxobutanoate by NaBH4 in methanol is

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

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

O O
CHO 1. NaOEt
C C
+ O Et 2. H3O+
Et
O2N
H H
C COOH C COOH
C C

(A) O2N CH3 (B) O2N H

CH3 CH3
C COOH C H
C C

(C) O2N H (D) O2N COOH

1. Mg/diethyl ether
33. Cl Br Product
2. CH2O
+
3. H2O
The product in the above reaction is

(A) Br CH2OH (B) Cl CH2OH

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 CH3

(C) Cl CH2OH (D) HOH2C CH2OH

34. Which of the following reactions give(s) a meso-compound as the main product ?
Br2 H2
(A) CH2Cl2
(B) Pd-C

H2 Br2
(C) Lindlar's catalyst (D) CCl4

35. Me – C ≡ C – Me 
Na/NH3 (liq.)
EtOH,−33°C
→ X 
dil.alkaline KMnO4
→ Product(s)

The product(s) from the above reaction will be

Me Me Me Me
H OH H OH HO H HO H
(A) (B) (C) (D)
HO H H OH H OH HO H
Me Me Me Me

36. One of the products of the following reaction is P.

O

CCl3 (i) aq. KOH P

+
(ii) H3O

Structure of P is:
O O O
HO O
Cl
CO2H H OH
(A) (B) (C) (D)
Cl

37. For the reaction below, the product is Q.

CO2H
Acetic anhydride
Q[C9H8O4]
Conc. H2SO4 (cat.) heat
HO
The compound Q is
CO2H COOCOCH3 CO2H CO2H
COCH3
(A) (B) (C) (D)
COCH3
OCOCH3 OH OH OH
38. Cyclopentanol on reaction with NaH followed by CS2 and CH3I produces a/an
(A) ketone (B) alkene (C) ether (D) xanthate

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39. The correct order of the addition reaction rates of halogen acids with ethylene is
(A) hydrogen chloride > hydrogen bromide > hydrogen iodide
(B) hydrogen iodide > hydrogen bromide > hydrogen chloride
(C) hydrogen bromide > hydrogen chloride > hydrogen iodide
(D) hydrogen iodide > hydrogen chloride > hydrogen bromide

40. Oxidation of allyl alcohol with a peracid gives a compound of molecular formula C3H6O2, which
contains an asymmetric carbon atom. The structure of the compound is
H H
OH
O OH O
(A) O OH (B) H3C (C) H3C (D) H3C
H
O H

41. CH3–C ≡ C MgBr can be prepared by the reaction of

(A) CH3–C ≡ C–Br with MgBr2 (B) CH3–C ≡ CH with MgBr2
(C) CH3–C ≡ CH with KBr and Mg metal (D) CH3–C ≡ CH with CH3MgBr

42. The number of alkene(s) which can produce 2-butanol by the successive treatment of
(i) B2H6 in tetrahydrofuran solvent and (ii) alkaline H2O2 solution is
(A) 1 (B) 2 (C) 3 (D) 4

43. Identify 'M' in the following sequence of reactions

CH3
Cl
C8H6Cl2O 
NH3
→ C8H8CINO →
Br2
NaOH
M
H2N
O
O C
Cl
Cl C
(A) Cl (B) Cl
CH3 CH3
CHO Cl
Cl
C
(C) Cl (D)
CH2Cl O CH3

44. Methoxybenzene on treatment with HI proudces

(A) iodobenzene and methanol (B) phenol and methyl iodide
(C) iodobenzene and methyl iodide (D) phenol and methanol

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45. If aniline is treated with conc. H2SO4 and heated at 200°C, the product is
(A) anilinium sulphate (B) benzenesulphonic acid
(C) m-aminobenzenesulphonic acid (D) sulphanilic acid

46. [P] 

Br2
→ C2H4Br 
NaNH2
NH
→ [Q]
3

Zn −Hg/HCl
[Q] 
20% H2SO4
Hg2 + , ∆
→ [R]  → [S]

The species P, Q, R and S respectively are

(A) ethene, ethyne, ethanol, ethane (B) ethane, ethyne, ethanal, ethene
(C) ethene, ethyne, ethanal, ethanol (D) ethyne, ethane, ethane, ethanal

47. The number of possible organobromine compounds which can be obtained in the allylic
bromination of 1-butene with N-bromosuccinimide is
(A) 1 (B) 2 (C) 3 (D) 4

48. The possible product(s) to be obtained from the reaction of cyclobutyl amine with HNO2 is/are
O
OH CH2OH
(A) (B) (C) (D) H2C=CH2

49. The major products obtained in the following reaction is/are

H3C H
C=C + Br2
H C2H5
CH3 CH3 CH3 CH3
H Br H Br Br H Br H
(A) (B) (C) H (D) Br
H Br Br H Br H
C2H5 C2H5 C2H5 C2H5

50. The isomerisation of 1-butyne to 2-butyne can be achieved by treatment with

(A) hydrochloric acid (B) ammoniacal silver nitrate
(C) ammoniacal cuprous chloride (D) ethanolic potassium hydroxide

51. The structure of the product P of the following reaction is

OH
(i) CO2 (high temperature
and high pressure
+ NaOH P
(ii) H3O+
OMe

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 OH OH OH OH
CO2H CO2H CO2H
(A) (B) (C) (D)
CO2H HO2C CO2H
OMe OMe OMe OMe

52. For the reaction below

(i) PhMgBr, THF
+
(ii) H3O
CN

Ph Ph Ph Ph
(A) (B) (C) CN (D)
OH O NH2

53. The reaction sequence given below given product R.

CO2Me (i) Ag2O
HO2C R
(ii) Br2, CCl4

The structure of the product R is

Br
(A) Br (B) CO2Me
CO2H
HO2C
CO2Me
MeO2H
(C) HO2C (D)
Br
Br

O
54. Reaction of the lactol S with NaOH followed by
OH

O
(A) O (B)

(C) OH (D)
OH OH

55. The reduction of benzenediazonium chloride to phenyl hydrazine can be accomplished by

(A) SnCl2, HCl (B) Na2SO3 (C) CH3CH2OH (D) H3PO2

56. The major product(s) obtained form the following reaction of 1 mole of hexadeuteriobenzene
is/are

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 D
D D
(i) Br2 (1 mole), Fe

D D (ii) H2O
D
D
D D
D D
D Br D D
D
(A) D D (B) D D
D D
D D
Br Br D H

(C) D D (D) D D
Br D
57. Amongst the following compounds, the one that will not respond to Cannizzaro reaction upon
treatment with alkali is
(A) Cl3CCHO (B) Me3CCHO (C) C6H5CHO (D) HCHO

58. Which of the following will be dehydrated most readily in alkaline medium?
O

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

59. Which of the following reactions will not result in the formation of carbon-carbon bonds?
(A) Cannizzaro reaction (B) Wurtz reaction
(C) Reimer-Tiemann reaction (D) Friedel-Crafts acylation

60. The correct structure of the drug paracetamol is

OH OH Cl Cl

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

CONH2 NHCOCH3 CONH2 COCH3

61. Ozonolysis of an alkene produces only one dicarbonyl compound. The structure of the alkene
is

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 (A) CH3 – CH = CH – CH3 (B)

(C) (D) CH3 – CH = CH – CH = CH2

62. Identify X in the following sequence of reactions.

(i) NaNH2
CH3 – CH – CH – CH2 – CH2 – CH3 X
(ii) Na in liquid NH3
Br Br
H3C H
CH3 – CH – CH – CH2CH2CH3
(A) (B) C=C
Br NH2 H CH2CH2CH3
H3C CH2CH2CH3 CH3 – CH – CH – CH2CH2CH3
(C) C=C (D)
H H NH2 NH2

63. The major products obtained during ozonolysis of 2, 3-dimethyl-1-butene and subsequent
reductions with Zn and H2O are
(A) methanoic acid and 2-methyl-2-butanone
(B) methanal and 3-methyl-2-butanone
(C) methanol and 2, 2-dimethyl-3-butanone
(D) methanoic acid and 2-methyl-3-butanone

64. Amongst the following compounds, the one(s) which readily react with ethanolic KCN.
(A) Ethyl chloride (B) Chlorobenzene
(C) Benzaldehyde (D) Salicylic acid

CH3
HBr (1 eqyiv.)
65. CH2 The major product of the above reaction is
H2C
CH3
CH3 CH3
(A) (B)
Br H3C Br

CH3
CH2 CH3
(C) H C (D)
2
Br H3C Br

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 Cl
NH3
66. The product of the above reaction is
EtOH
Br
Cl
NH2 NH2 NH2

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

NH2 Br OEt
NH2

67. 1, 4-dimethylbenzene on heating with anhydrous AlCl3 and HCl produces

(A) 1, 2-dimethylbenzene (B) 1, 3-dimethylbenzene
(C) 1, 2, 3-trimethylbenzene (D) ethylbenzene

CHO –
OH
68. ? The product of the above reaction is
CHO
CH2OH CH2O–
(A) (B)
COOH COOH
CH2OH CH2O–
(C) (D)
–
COO COO–

69. The reaction of methyltrichloracetate (Cl3CCO2Me) with sodium methoxide (NaOMe)

generates
(A) carbocation (B) carbene (C) carbanion (D) carbon radical

70. Best reagent the nuclear iodination of aromatic compounds is

(A) Kl/CH3COCH3 (B) I2/CH3CN
(C) KI/CH3COOH (D) I2/HNO3

+
Ether, H3O
71. In the reaction R MgBr + HC(OEt)3 P the product P is
(A) RCHO (B) R2CHOEt (C) R3CH (D) RCH(OEt)2

72. Identify the correct method for the synthesis of the compound shown below from the following
alternatives
CH3

O2N

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 CH3CH2CH2CH2Cl HNO3
(A)
AlCl3 H2SO4

CH3CH2CH2COCl Zn/Hg HNO3

(B)
AlCl3 HCl/Heat H2SO4

CH3CH2CH2COCl HNO3 Zn/Hg

(C)
AlCl3 H2SO4 HCl/Heat

CH3CH2CH2COCl KMnO4 HNO3

(D) –
AlCl3 OH H2SO4

POC, BIOMOLECULE, POLYMER AND CHEMISTRY IN EVERYDAY LIFE

73. Haloform reaction with I2 and KOH will be responded by
O O
OH
O Me
(A*) I Ph (B*) Ph (C) Me Ph (D) Ph N Me
OH Me H

74. C4H10O 

K 2Cr2O7
H SO
→ C4H8O 
I2 /NaOH
Warm
→ CHI3
2 4
N

Here, N is
OH
(A) OH (B) (C) O (D) OH

75. Which one of the following is a condensation polymer ?

(A) PVC (B) Teflon (C) Dacron (D) Polystyrene

76. ADP and ATP differ in the number of

(A) phosphate units (B) ribose units (C) adenine base (D) nitrogen atom

77. The compound that would produce a nauseating smell/odour with a hot mixture of chloroform
and ethanolic potassium hydroxide is
(A) PhCONH2 (B) PhNHCH3 (C) PhNH2 (D) PhOH

78. Which of the following compound would not react with Lucas reagent at room temperature?
(A) H2C = CHCH2OH (B) C6H5CH2OH
(C) CH3CH2CH2OH (D) (CH3)3COH

79. Amongst the following compounds, the one which would not respond to iodoform test is
(A) CH3CH(OH)CH2CH3 (B) ICH2COCH2CH3
(C) CH3COOH (D) CH3CHO
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80. In the Lassaigne’s test for the detection of nitrogen in an organic compound, the appearance
of blue coloured compound is due to
(A) ferric ferricyanide (B) ferrous ferricyanide
(C) ferric ferrocyanide (D) ferrous

81. An amine C3H9N reacts with benzene sulphonyl chloride to form a white precipitate which is
insoluble in aq. NaOH. The amine is
Me Me
N Me Me
(A) (B) N Me (C) NH2 (D)
Me H Me Me NH2

82. In DNA, the consecutive deoxynucleotides are connected via

(A) phosphodiester linkage (B) phosphomonoester linkage
(C) phosphotriester linkage (D) amide linkage

83. Within the list shown below, the correct pair of structures of alanine in pH ranges 2-4 and 9-11
is

I. H3N+ – CH(CH3)CO2H II. H2N – CH(CH3)CO2–

III. H3N+ – CH(CH3)CO2– IV. H2N – CH(CH3)CO2H

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

ANSWER KEY
1. (C) 2. (B) 3. (D) 4. (C) 5. (D)
6. (B) 7. (A) 8. (D) 9. (D) 10. (D)
11. (A) 12. (A) 13. (A) 14. (A) 15. (C)
16. (A) 17. (B) 18. (D) 19. (A) 20. (C)
21. (D) 22. (A) 23. (B) 24. (C) 25. (B)
26. (BD) 27. (C) 28. (C) 29. (C) 30. (C)
31. (C) 32. (A) 33. (D) 34. (B) 35. (AC)
36. (C) 37. (A) 38. (D) 39. (B) 40. (A)
41. (D) 42. (B) 43. (B) 44. (B) 45. (D)
46. (A) 47. (A) 48. (AC) 49. (AD) 50. (D)
51. (C) 52. (B) 53. (D) 54. (C) 55. (A)
56. (A) 57. (A) 58. (B) 59. (A) 60. (B)
61. (B) 62. (B) 63. (B) 64. (AC) 65. (B)
66. (C) 67. (B) 68. (C) 69. (B) 70. (D)
71. (A) 72. (B) 73. (AB) 74. (B) 75. (C)
76. (A) 77. (C) 78. (C) 79. (C) 80. (C)
81. (B) 82. (A) 83. (A)

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