[Organic Halides & Organic Concepts]

SECTION-1 SINGLE CORRECT ANSWER TYPE

1. KI in acetone, undergoes SN2 reaction with each P, Q, R and S. The rates of the reaction vary as :

(A) P  Q  R  S (B) S  P  R  Q (C) P  R  Q  S (D) R  P SQ

2. The following compound on hydrolysis in aqueous acetone will give :

It mainly gives
(A) K and L (B) only K (C) L and M (D) only M

3. The compound, which undergoes SN1 reaction most rapidly is :

(A) (B) Br (C) Br (D) Br
Br
 CH3 h
4. CHCH2CH3 + Cl2  ‘N’ isomers of C5H11Cl
CH3 Fractional distillation

‘n’ distilled products

The values of ‘N’ and ‘n’ are :
(A) 6, 6 (B) 6, 4 (C) 4, 4 (D) 3, 3

5. Which of the following alkyl halide would be most likely to give a rearranged product under SN1
conditions?

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

6. A compound (A) of formula C3H6Cl2 on reaction with alkali can give compound (B) of formula C3H6O
or compound (C) of formula C3H4 depending upon the conditions employed. Compound (B) on
oxidation gave a compound of the formula C3H6O2. Compound (C) with dilute H2SO4 containing Hg2+
ion gave compound (D) of formula C3H6O, which on reaction with bromine and NaOH gave the
sodium salt of C2H4O2. The most probable structure of compound (A) would be
(A) ClCH2CH2CH2Cl (B) CH3CCl2CH3
(C) CH3CH2CHCl2 (D) CH3CHClCH2Cl

7.

The product A is :

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

8. Identify the set of reagents/reactions conditions X and Y in the following set of transformations-
X Y
CH3  CH 2  CH 2 Br   Pr oduct   CH 3  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 aqueous NaOH, 80°C, Y = Br2/CHCl3, 0°C
 Br
O
9. The nucleophilic substitution of (S)–CH3 – CH – C with dilute OH– followed by acidification
OH
gives :
OH OH
O O
(A) (R)-CH3 – CH – C (B) (S)-CH3 – CH – C
OH OH
OH OH
O O
(C) (R)-CH3 – CH – C (D) (S)-CH3 – CH – C
O– O–

10.

Product (B) is :

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

11. How many stereoisomers are possible for 1,3 dibromocyclopentane ?

(A) 6 (B) 4 (C) 3 (D) 2

12. Equal amount of a RCl (C4H9Cl) is reacted at the same temperature with equal volume of 0.2M and
0.4M solution of KOH, respectively, in two separate experiments. The time taken for the reaction of
50% of (C4H9Cl) was found to be same, the alkyl halide is :
Cl
(A) Me (B)
Me

(C) Me Cl (D)

13. In the given reaction

The compound (X) is :

OCH3 Cl OCH 3
Cl
Cl
Cl OCH3 Cl

(A) O OCH3 (B)

O OCH3 (C) O Cl (D) O Cl
14. The correct stability order for the following species is :

(A) (II) > (I) > (IV) > (III) (B) (I) > (II) > (III) > (IV)
(C) (II) > (I) > (IV) > (III) (C) (I) > (III) > (II) > (IV)

15. (I) Me — I + OH  MeOH + I (II) Me — I + NH3  MeNH3

  

(III) Me2S — Me + OH  MeOH + (IV) Me2S — Me + NH3  MeNH3 +
In whichMeof Sthe above given SN2 reactions, rate of the Me S increases on increasing the polarity of
reaction
the solvent ?
(A) (I) (B) (II) (C) (III) (D) (IV)

SECTION-2 LINK-COMPREHENSION TYPE

PARAGRAPH FOR QUESTIONS 16 - 18

In the following reaction sequence, products I, J and L are formed. K represents a reagent.

16. The structure of the product I is :

17. The structures of compounds J and K, respectively, are :

18. The structure of product L is :

PARAGRAPH FOR QUESTIONS 19 - 20
Any compound with a chiral centre can be represented by
(a) 2D – representations – Fischer & Newmann projections
(c) 3D- representation – Saw Horse projections.
In order to make the correct interpretations, the 2D-representations must be converted to 3D-representations
and then the physical parameter or chemical reactions are studied. Alcohols react with HX to form
alkyl halides as follows: R — OH  H — X  R — X  H 2 O
19. Which of the following conformations have zero dipole moment?

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

20.

The final product of the above reaction will be

(A) Enantiomers (B) Diastereomers
(C) Meso form (D) Optically active form(s)

SECTION-3 MULTIPLE CORRECT ANSWER TYPE

21. Consider the reactions T and U

CH3 CH3

H D EtO K   D H 
EtO K 
T: 
EtOH U: 
EtOH
H Br H Br
CH3 CH3
(A) T gives cis-2-butene with loss of deuterium
(B) T gives trans-2-butene with loss of deuterium
(C) U gives trans-2-butene without loss of deuterium
(D) T gives cis-2-butene without loss of deuterium

22. Which of the following is/are not mentioning major products in the given reactions?

(A)

EtOH
(B)
Br
Br
Ether
(C) ONa
O
NO2 NO2

(D) CF3 RO CF2

O2 N NO2
23. Treatment of A and B with conc. HCl gives the same two isomeric alkyl chlorides; then A and B are
(A) (A) = Me3C–CH=CH2 ; (B) = Me3C–CH(OH)Me
(B) (A) = H3C–CH2–CH=CH2 ; (B) = H3C–CH=CH–CH3
OH
(C)
A B
(D) (A) = Me2CH–CH=CH2 ; (B) = Me3C–CH=CH–CH3

24. The hyperconjugative stabilities of tert-butyl cation and 2-butene, respectively, are due to

25. Which of the following will not form a Grignard reagent on treatment with Mg in dry ether?
(A) BrCH2CH2Br
(B) BrCH2CH2CH2Br
(C) BrCH2CH2CH2CH2Br
(D) All the three above can form Grignard reagent.

26. The reactivity of compound Z with different halogens under appropriate conditions is given below:

The observed pattern of electrophilic substitution can be explained by

(A) the steric effect of the halogen
(B) the steric effect of the tert-butyl group
(C) the electronic effect of the phenolic group
(D) the electronic effect of the tert-butyl group

27. Among the following, the number of reaction(s) that produce(s) benzaldehyde is :

28. The sequence of reagents used in that order to distinguish the following compounds taken in three
different test tubes:
(1) CH3–CH=CHCl (2) CH3CH2CH2Cl (3) CH2=CH–CH2Cl
would be
(A) Br2 in CCl4, alcoholic AgNO3 (B) Cold alkaline KMnO4, ammoniacal AgNO3
(C) Alcoholic AgNO3, Br2 in CCl4 (D) Ammoniacal AgNO3, cold alkaline KMnO4
29. Which of the following reaction will proceed with retention of configuration only at the chiral centre ?
C2H5
H
O–
dil. OH– H2O
(A) CH3 – C – C (B) CH3 – C – Br
O C2H5
Br

CH3
CH3
H2O H2O
(C) C6H5 – C – Br (D) C – CH2 – S – CH3
Ag+

C2H5 H
I
30. The major product in the following reaction is :

(A) (B)

(C) (D)

SECTION-4 COLUMN MATCHING TYPE

31. Match the Column-I and Column-II :

Column I Column II

(A) Cl is less reactive than Cl (p) S N1

Cl
Cl
(B) CH3 (q) S N2
is less reactive than

Cl
Cl
(C) (r) E1
is less reactive than

CH3 H3 C Cl
H3 C
(D) C C C C (s) E2
is less reactive than
H H CH3
Cl
32.
Column I Column II
H
CH3 Br CH3
(A) alc. KOH (p)
H H CH3–C=CH–CH3
Et

CH3
H H alc.KOH
(B) (q) E2
Et F
H
CH3
H H pot.t.butoxide
CH3
(C) (r)
Et Br CH2=C–CH2–CH3
H
H
CH3 Et pot.t.butoxide
(D) (s) E1CB
H H
F

33. Match the Column-I and Column-II :

Column I Column II

OH
(A) CHCl3   (p) ElCB mechanism

C 2 H5 O
(B) CHCl2  CF3  (q) Benzyne mechanism

O
(C) Br2/CCl4 (r) , -elimination
R C OAg

NaOH
(D) Cl (s) Free radical mechanism
high temperature pressure
34.
Column I Column II
Cl
NO2
(A) NaOH (p) Nucleophilic substitution

NO2
F
(B) EtO–Na+ (q) Elimination
CH3–CH–CH2CH3 in EtOH

CH3
CH3O–Na
(C) CH3–C–Br in MeOH (r) Carbanion
CH3
CH3 E2 E
(D) NaNH2 (s)  1
CH3CH2–CH–CH2–Br in liq. NH3 SN 2 SN 1

SECTION-5 INTEGER TYPE

35.

The total number of possible substitution product will be :

36. The number of uncharged resonating structures of

are ……….

37. On conversion into Grignard reagent followed by treatment with water, how many alkyl bromide
would yield isopentane?
38. How many structural methyl ketones of molecular mass 100 are possible?

39. The total number of contributing structure(s)

showing hyperconjugation (involving C-H bonds)
for the following species is/are _______

40. How many of the following compounds reac with CH3MgBr to liberate CH4 gas ?
41. How many of the following compounds can undergo SN1 reaction at significant rate with H2O ?

42. Find the total number of monochlorinated products formed from the pure reactant given below :


H Br2


 Possible products   Products
43. CCl4
x x
OH

The total number of possible products (x + y)

(including stereoisomerisms) is / are ____________.

44. How many of the following reactions can be used to prepare Aryl Halide.
CH3

CH2 Br2 /CCl4

COOAg 
(A)  (B) Cl2 /h
 

Br2 /CCl4
(C)   (D)

N2Cl
HCl 1/2O2
 
(E) HBF4
(F)




45. How many of the following subtrates will react faster when compared with 1-bromopropane towards
SN1 reaction in similar conditions?
(i) CH3  CH  CH  Br (ii) CH 2  CH  CH 2 Br

(iii) CH3  Br (iv) C6 H 5CH 2 Br

(v) C6 H 5Br (vi)

(vii)  CH 3 3 CBr (viii) (CH3 )2 CHBr

(ix)
Br
46. How many of the following solvents are suitable for SN 2 reactions?

47.

Which of the following Cl is substituted on treatment with NaOMe in MeOH?

48. How many of the given species are aromatic in character ?

49. List the following compounds in the order of their decreasing boiling point.

Report the sum of numbers pertaining to compounds with lowest & highest B.P.
 [Organic Halides & Organic Concepts]
1 2 3 4 5 6 7 8 9 10
B A D B C C A B B B

11 12 13 14 15 16 17 18 19 20
C D A D B D A C C B
21 22 23 24 25 26 27 28 29 30

BCD BC ABC A AB ABC ABCD AC AD D

31 32 33

[A-p, q, r, s] [B-p, q, r, s] [C-q] [D-s] [A-p, q] [B-r, s] [C-q, r] [D-r, s] [A-p, r] [B-p] [C-s] [D-p, q]
34 35 36 37 38 39 40
[A-p, r] [B-q, r] [C-q, s] [D-p, q] 4 6 6 4 8 9

41 42 43 44 45 46 47 48 49
7 6 8 3 5 6 3 9 8