1. Which alkyl halide will react fastest with aqueous ethanol ?

(A) (CH3)3C – Br (B) (CH3)3C – Cl

(C) (CH3)2CH – Br (D) CH3 – CH2 – CH2 – Br

2. When the concentration of alkyl halide is tripled and the concentration of OH¯ ion is reduced to
half, the rate of SN2 reaction increases by:
(A) 3 times (B) 2 times (C) 1.5 times (D) 6 times

3. An S N 2 reaction at an asymmetric carbon of a compound always gives:

(A) an enantiomer of the substrate
(B) a product with opposite optical rotation
(C) a mixture of diastereomers
(D) a single stereoisomer

4. In the given reaction, CH3CH2 – X + CH3SNa 

The fastest reaction occurs when ‘X’ is -
(A) – OH (B) – F (C) – OCOCF3 (D) OCOCH3

Which of the following involves an “ SN ” route of reaction:

2
5.

(A) CH3Cl 
 (B) CH3MgCl + CH3Cl 
Na
ether

(C) CH3Cl + LiAlH4  (D) All

6. The compound which undergoes fastest reaction with aq. KOH solution is :
(A) C 6H5  CH  OCH 3 (B) C 6H5  CH  CH3 (C) C6H5 – CH2 – CH2 – Cl (D) C6H5  CH  CH2  CH3
| | |
Cl Cl Cl

7. The rate of S N1 reaction is fastest with:

(A) (B)

(C) (D)

8. In the following reaction the most probable product will be:

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

RESONANCE 2 1
9. In the following reaction :


NaI
Acetone

‘X’ [The structure of ‘X’ can be]

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

10. The following reaction is described as:


  
NaOH

(A) SN1 with racemisation

(B) intramolecular SN2 with walden inversion

(C) intramolecular SN2 with retention of configuration

(D) intermolecular SN1 with recemisation

11. The insecticide chlordane is warmed with dilute NaOH solution for some time. The expected
product would be :

(A) (B)

(C) (D)

12. Which configuation will be adopted by the poduct at cabon atoms marked (1) and (2) respectively
in the given reaction.

+ CH3CH2  CH  CH3  

Ether
|
(D) Br
(A) D, D (B) D, L (C) L, L (D) L, D

RESONANCE 2 2
13. Which of the following will undergo fastest elimination reaction with alcoholic KOH.

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

14. When all-cis isomers of C6H6Cl6 (1, 2, 3, 4, 5, 6 - Hexachlorocyclohexane) is heated with alc.
KOH, the most probable product is :

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

15. The most probable product in the following reaction is :

Trans

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

16. Which product(s) will be formed in the following reaction :

  

alc. KOH


(A) No reaction (B) Trans alkene (C) cis alkene (D) cis + trans alkene

17. What will be the major product of the following reaction

CH3 CH3
| | CH3OH, 30C
CH3  C  C  CH  CH3    
| | |
H CH3 Br

CH3 CH3 CH3 CH3 CH3 CH3

| | | | | |
(A) CH3  C  C  C  CH3 (B) CH3  C  C  CH  CH3
| | |
OCH3 H H

CH3 CH3 CH3 CH3 CH3

| | | | |
(C) CH3  C  C  C  CH3 (D) CH3  C  C  CH  CH2
| | | | |
H OCH3 H H CH3

RESONANCE 2 3
18. Which of the following reaction will undergo an elimination reaction and an alkene will be formed in
the products.

Zn dust, 
(A)    
 (B)

alc. KOH,  conc H SO , 

(C)     (D)   2 
4


19. When (1R, 2R)-1, 2-dibromo-1, 2-diphenyl ethane is treated with alcoholic solution of KOH, the
most probable product would be :
(A) trans-1, 2-diphenyl ethene (B) A mixture of cis, trans alkenyl bromide
(C) cis-alkenyl bromide (D) trans-alkenyl bromide

20. Compound A (C5H9Cl) on treatment with a strong base produced only one compound ‘B’ (C5H8)
exclusively. B on reductive ozonolysis produces C(C5H8O2). A does not decolourise Baeyer’s re-
agent. ‘A’ can be:

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

21. Which of the following products is formed when m-bromochlorobenzene is treated with magne-
sium in the presence of ether ?

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

22. The end product Y of the reaction is :

 H O
C2H5MgBr + S  X    Y
3

(A) C2H6 (B) C2H5SMgBr (C) C2H5SH (D) none of these

Answers
E X E R C I S E -1
1. A 2. C 3. D 4. C

5. D 6. A 7. A 8. B

9. A 10. B 11. D 12. B

13. A 14. B 15. C 16. C

17. C 18. B 19. D 20. B

21. A 22. A

RESONANCE 2 4
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. Predict the compound in each pair that will undergo solvolysis (in aqueous ethanol) more
rapidly.
(a) (i) (CH3CH2)2CH – Cl (ii) (CH3)3C – Cl (b) (i) (ii)

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

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

3. The correct decreasing order of relative reactivity of the following bromides towards hot aqueous
KOH solution is:
(I) CH3 – CH2 – Br (II) CH3 – CH2 – CH2 – Br

(III) OH – CH2 – CH2 – Br (IV) CH3 – – CH2 – Br

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

4. For a given alkyl halide, the ease of formation of Grignard reagent is:
(A) RI > RBr > RCl (B) RI > RBr < RCl
(C) RI < RBr < RCl (D) RI > RCl > RBr

5. The correct order of reactivity of the following halides for bimolecular elimination is :
(I) (CH3)2 CH – CHI – CH3 (II) (CH3)2CH – CH2 – CH2 – I

(III) CH3 – CH2 – CHI – CH3 (IV) (CH3 )2 C  CH2  CH3

|
I

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

RESONANCE 2 5
6. 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

7. 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

8. 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

9. 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

10. In the following compound, arrange the reactivity of different chlorine atoms towards NaSH in
decreasing order.

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

11. The reactivity order of CH3MgBr with the following reagents is

(I) PhOH (II) CH3CHO (III) R–C  CH (IV) CH3  C  Cl

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

RESONANCE 2 6
12. 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

13. 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

RESONANCE 2 7
(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)

RESONANCE 2 8
 Answers
E X E R C I S E -2
1. (a) (i) > (ii) (b) (ii) > (i) (c) (ii) > (i)
(d) (ii) > (i) (e) (ii) > (i) (f) (i) > (ii)

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

3. D 4. A 5. D 6. D 7. C

8. D 9. B 10. 2>4>1>3 11. D

12. (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

13. (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

RESONANCE 2 9