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guru

1. Predict the compound in each pair that will undergo the SN2 reaction faster.

(a) (i) (ii) (b) (i) (ii)

(c) (i) (ii) (d) (i) (ii)

(e) (i) (ii) (f) (i) (ii)

2. The relative reactivity of following halides towards ethanol follows the order:
(I) CH3 – – Cl (II) CH3CH2Cl (III) CH3 – O – CH2 – Cl (IV) C6H5– CH2 – Cl

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

3. The increasing order of reactivity of the following isomeric halides with alcoholic AgNO3 is :

(I) C6H5 – CH = CH – CH2 – CH2 – Cl (II) C 6H5  CH  CH  CH  CH3

|
Cl

CH3
|
(III) C 6H5  C  CH  CH2  CH3 C H
(IV) 6 5  C  CH  CH2
| |
Cl Cl

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

4. Rate of S N1 reaction is :

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

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

5. Rate of reaction with aqueous AgOH solution follows the order.

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

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

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6. Arrange the followings in decreasing order of reactivity towards SN2 reaction :

I II III IV
(i) CH3Cl CH3CH2Cl CH3CH2–CH2–Cl CH3CHClCH3

(ii) CH3CH2 CH2Cl CH3 CH2CH2Cl CH3CH2CH2CH2Cl CH3CH2CH2

CH3 CH3
CH3
| | |
(iii) CH3  C  CH2  Cl CH3 – C – Cl CH3  C  Cl CH3 – CH2 – Cl
| | |
CH3 CH3 H

(iv)

(v) Br – CH2 – CH2 – Br N  C – CH2 – Br CH3  CH  CH3 CH3 – CH2 – Br

|
Br

(vi) CH3CH2Cl CH2 = CH – CH2Cl CH3Cl CH2 = CHCl

(vii) CH3–O–CH2–Cl H  C  CH2  Cl CH3–CH2–Cl CH3–Cl

||
O

(viii)

(ix) HO–H2C–CH2–Cl CH3–CH2–Cl CH3–CH2–CH2–Cl CH3  C  Cl

||
O

7. Arrange the following in decreasing order of reactivity towards SN1 reaction :

I II III IV
(i) CH3Cl CH3CH2Cl CH3CH2–CH2–Cl CH3CHClCH3

CH3 CH3 CH3

| | |
(ii) CH3–CH2–CH2–Cl CH3  CH  CH2  Cl CH3  C  CH2  Cl CH3  C  Cl
| |
CH3 CH3

(iii) CH3CH2 CH2Cl CH3 CH2CH2Cl CH3CH2CH2CH2Cl CH3CH2CH2

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(iv)

(v)

(vi)

CH3
|
(vii) CH2=CH–CH2–Cl CH2  CH  CH  Cl CH3–CH=CH–CH2–Cl CH3  C  CH  CH3
|
Cl

CH3 O
| ||
(viii) C 6H5  C  Br CH3  C  CH  Br (CH3)2CHBr
| |
CH3 CH3

(ix) (C6H5)2CHCl CH2 = CH CH2Cl C6H5 CH2Cl

(x)

(xi)

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8. Which of the following reaction(s) follow the same pattern of energy graph for the formation of major
product only.

P.E.

Reaction progress
OH

(A*) +
H

OH

(B*) +
H

OH

(C*) +
H


CH3 CH3
H+
(D*) CH – CH – CH 2 – OH


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1.
Answers
(a) (i) > (ii) (b) (ii) > (i) (c) (ii) > (i)
(d) (ii) > (i) (e) (ii) > (i) (f) (i) > (ii)

2. D 3. C 4. D 5. B

6. (i). I > II > III > IV (ii). III > II > I > IV (iii). IV > III > I > II

(iv). I > III > II > IV (v). II > I > IV > III (vi). II > III > I > IV

(vii). II > I > IV > III (viii). IV > I > III > II (ix). IV > I > II > III

7. (i). IV > III > II > I (ii). IV > III > II > I (iii). IV > I > II > III

(iv). IV > I > II > III (v). I > II > III > IV (vi). III > II > I > IV

(vii). II > III > I > IV (viii). II > I > IV > III (ix). II > IV > III > I

(x). II > IV > I > III (xi). IV > II > III > I

8. A, B, C, D

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CH 3
| conc.H SO
Q.1 CH 3CH 2CH 2CH 2CCH 2OH  24  Major product is:

|
CH 3

CH 2
||
(A) CH3CH2CH2CH2CH= (B) CH 3CH 2CH 2CH 2C
|
CH 2CH 3

(C) CH 3CH 2CH 2CH 2C  (D) CH 3CH 2 CH 2CH  C  CH 2CH 3

| |
CH 3 CH 3

Q.2 Treatment of 2, 2, 6, 6 tetramethyl cyclohexanol with acid leads to the formation of alkene after
rearrangement. The structure of alkene is

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

Q.3 P is

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

Q.4 Dehydration product of 1,4-diol given below will be

CH 3CHCH 2CH 2CH 2 H3PO
4 

| |
OH OH
18

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


Q.5 The product(s) of the reaction H
 is:


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

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

Q.6 alc
. KOH



final product of above reaction is isolated as

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

Q.7 Dehydrohalogenation by a strong base is fastest in.

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

Q.8 In which case an alkene is formed on reaction with a strong anionic base.

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

Q.9 Which one of the following hexachlorocyclohexane is least reactive and which one is most
reactive in E2 reactions with a strong base for dehydrohalogenation.

(A) I least & II most (B) II least & I most

(C) III least & I most (D) III least & II most

alcoholic , KOH
Q.10    
 A
E 2

(A) (B) (C) (D) None is correct

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Q.11 Which of following are correct for given reaction




(A) Major product of reaction is (B) Major product is

(C) The reaction is thermal elimination reaction (D) The reaction is E1 reaction

Q.12 Which alkyl halide undergo E2 elimination

(A) (B)

(C) (D)

Q.13 In the given pairs, which pair represent correct order of rate dehydrohalogenation reaction.
(A ) < (B) <

(C) < (D) CH3–CH2–Cl < CD3 – CD2 – Cl

I Br

Q.14 The major product formed in the following reaction is :

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

Q.15 The rate of elimination (using EtONa) of:

Br Br

(I) (II) (III)

Br
t-Bu t-Bu
(A) I > II > III (B) I > III > II (C) II > I > III (D) III > I > II

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Q.16 Consider the reaction.

CH 3
| —
OH
CH 2  CH  CH 2  CH  CH  CH 3  Product Major..
|
Cl
The major product is
CH 3 CH 3
| |
(A) CH 2  CH  CH  CH  CH  CH 3 (B) CH 2  CH  CH  CH 2  CH  CH 3

CH 3 CH 2
| ||
(C) CH 2  CH  CH 2  CH  CH  CH 3 (D) CH 2  CH  CH 2  CH 2  C  CH 3

Br H
H
H3C alcoholic , KOH
Q.17    
 A
E 2

Ph
Ph

CH3 Ph CH3 Ph H CH3

C C C
(A) (B) (C) (D) None is correct
C C C
H Ph Ph H Ph Ph

CH I Ag O , H O
Q.18 3
  2 
2
 H


The structure of 'H' is

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


Q.19 H


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

Q.20 Among the given compounds, the correct dehydration order is:

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

(A) I < II < III < IV (B) II < III < IV < I (C) I < III < IV < II (D) I < II < III = IV
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Q.21

OH
80°C P+Q+R +S
Br

S
P.E. R
Q

P
Br

Reaction co-ordinates
Correct statement(s) about reaction & related graph is (are):
(A) P & Q are nucleophilic substitution products by SN2 reaction mechanism
(B) only R & S are elimination products by E2 reaction mechanism
(C) P is nucleophilic substitution product by SN2 reaction mechanism
(D) Q,R,S are elimination products by E2 reaction mechanism

Q.22 H
 P. The product P is:

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

Q.23 How many 1,2-Shifts are involved during the course of following reaction:

conc . H SO
 24 

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

Q.24 Rate of dehydration when given compounds are treated with conc. H2SO4.

(P) (Q) (R) (S)

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


Q.25 
 Which of the following product cannot be obtained by this reaction.
Ei

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

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Q.26 Match the following

List-I List-II


CH CH O
(A) 3 
2
 (P) E1



CH 3CH 2 O
(B)   
 (Q) E2
CH 3CH 2OD

Ag O
2
(C)   (R) E1cb
moist

(D) alc
. KOH
 (S) Ei

Q.27 Match the List I (reaction) with List II (reaction intermediate) and select the correct answer using the
codes given below the Lists.
List I List II
(A) CF3–CHCl2 alc /
.KOH
  CF2 = CCl2 (1) Transition state

CH 3
| 
(B) CH 3  C  OH H
 CH 3  C  CH 2 (2) Carbocation
| |
CH 3 CH 3
alc.KOH
(C) CH3–CH2–Br  CH2=CH2 (3) Carbanion


Br
|
(D) CH 3  C  CH 3 aq
. KOH
 /
  CH 3  C  CH 2 (4) Free radical
| |
CH 3 CH 3

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Answers
1. A 2. C 3. C 4. A
5. D 6. A 7. B 8. A
9. B 10. A 11. A 12. A, B
13. A 14. C 15. A 16. A
17. A 18. C 19. D 20. A
21. C, D 22. D 23. C 24. C
25. D
26. (A) – Q; (B) – R ; (C) – P; (D) – Q
27. (A)  3,(B)  ,(C)  1,(D)  2

Reaction Mechanism