S.No.

Compound Compare rate of SN2 Compare rate of SN1

1.

2.

3.

4.

5.

6.

7.

8.

9.

10. CH3 – O – CH2 – Br CH3 – CH2 – CH2 – Br

11.

12.

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 Answer Key
S 2 S 1
N N

Cl Cl Cl Cl

1. > >

Cl Cl Cl Cl
2. > >

Br Cl Br Cl
3. > >

Br Br
4. Br > Br
>

Cl Cl Cl Cl
5. > >

CH2Br CH2Br CH2– Br CH2Br

6. > >

Br > Br >
7.
Br Br
8. Br > Br Br > Br
O O
9. Br Br Br Br
> <

10. O Br > Br O Br > Br

Br Br
11. >
Br > Br

> >
12. Cl Cl
Cl Cl
Q. Identify major product and type of reaction (SN1 / SN2 /E1/E2).

S. No. Reaction SN1 / SN2 /E1/E2

CH2–Cl
CH3O
1.

CH3
2. H Cl NaI
acetone
Et
Cl
3. H D KSH
H D
CH3

4. Cl
Ph–S

Br

5.
KCN
Br

H2O
6.
Br

Br
7.

H2O

8. H OTos
NaCN
C ?
H3 C CH2OCH3

(S stereochemistry)
Br
CH3
9. H2O
?
Ethanol
H3C
H

Br

10.
HCO2H
H2O
?
S. No. SN1 / SN2 /E1/E2
O NaI
11. Br
acetone

O
CH3CONa
O2N CH2Cl
12. acetic acid

NaCN
Br
O ethanol–water
13.

H2O, HO
14. NC CH2Cl

O
15. NaN3
Cl
O acetone–water

O NaI
16.
TsO O acetone

SNa
17. + CH3CH2Br
O

OCH3
CH3O OH
18. 1. TsCl, pyridine

CH3O 2. LiI, acetone

19. Cl NaI (1 mol)

C5H10ClI
acetone
Cl

20.
Br SNa C4H8S2
Br + NaS

21. Cl + Na2S C4H8S

Cl
Cl OAc

22. CH3CO2– Na+

CH3CO2H, H2O

CH2Br CH2OAc
23. CH3CO2– Na+
DMF
S. No. SN1 / SN2 /E1/E2

24. n-propyl bromide + Me2NH

acetone
25.
OH
Br

triphenylphosphine
. 4-iodo-1-pentane
26.

t-butyl alcohol (SN)

27.
S Cl methanolysis

28. Br
OAc / Ag

Ph

29. . 3-iodopentane
sodium acetate / DMF

Cl
30.
NaSH (1 equiv)

Cl

31. ethanolysis (SN)

Cl

32. KCN / DMF

n-hexyl iodide

33. methanolysis (RT)

Cl

34. refluxing EtOH

Br

35.. Br CH3
+ Cl DMF
H H
O acetolysis (SN)
36..
Cl
S. No. SN1 / SN2 /E1/E2
D
37. H Br NaN3
D H DMF
CH3

38. Nal
Cl Acetone

Nal
39. Cl MeOH

40. CH3CO2H
Br

41. O
O Ethanol
F + S
25ºC
O

42.
 Br
C

⊕
43. ONa + I

44. NaI/Acetone + Cl

I
45. DMSO
NaSH +

DMF
46. NaN3 + I

MeOH
47. Cl
Cl

Cl
48 . NaCN
DMSO
Cl
49..
H2O
S. No. SN1 / SN2 /E1/E2

50. Br
1. One eq. NaCN
¾¾¾¾¾¾®

Br
51.
nBuBr + KCN nBuCN

OCH3
Me
CH3 C
H
52. Br NaOH NaH CH3I
(P) (Q)
DMSO

Aq. KOH
53.

Br
54. Me
–
MeO Na+
H Cl C
D
CH3
55. AgCN
CH3–C–Cl
CH3
Cl
56. Moist
CH3 Ag2O


57. CH 3OTs 
AgCN
 CH 3 N  C
58.
 Nucleophilic Substitution of Alkyl Halides (R–X)

Reagent Nucleophile Substitution Class of main

(Nu–) product R–Nu product
NaOH (KOH) HO– ROH Alcohol
H2O H2O ROH Alcohol

NaOR¢ R¢O– ROR¢ Ether

NaI I– R—I Alkyl iodide
NH3 NH3 RNH2 Primary amine
R¢NH2 R¢NH2 RNHR¢ Sec. amine
R¢R¢¢NH R¢R¢¢NH RNR¢R¢¢ Tert. amine
KCN RCN Nitrile
(cyanide)
AgCN Ag-CN: RNC Isonitrile
(isocyanide)
KNO2 O=N—O R—O—N=O Alkyl nitrite
AgNO2 Ag—Ö—N=O R—NO2 Nitroalkane
R¢COOAg R¢COO– R¢COOR Ester
LiAlH4 H RH Hydrocarbon
R¢ M
– +
R¢ –
RR¢ Alkane
1. Which of following compound will not undergo nucleophilic substitution reaction
Cl Cl Cl Cl

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

2. Most reactive toward SN2

O

(A) (B) Cl (C) Cl (D) Ph – C – CH2 – Cl

Cl

3. R–I R – Br R – Cl R–F
(a) (b) (c) (d)
rate of SN2 is
(A) a > b > c > d (B) b > a > c > d (C) a = b = c = d (D) d > c > b > a
4. R–I R – Br R – Cl R–F
(a) (b) (c) (d)
rate of SN1–
(A) a > b > c > d (B) b > a > c > d (C) a = b = c = d (D) d > c > b > a

Cl Cl

H2O reaction ––(1) H2O

reaction ––(2)
5.

reacton (1) & reaction (2) are

(A) SN1, SN1 (B) SN1, SN2 (C) SN2, SN1 (D) SN1, no reaction

Cl

H2O reaction ––(1)

6. Cl ; reaction -(1) & reaction-(2) are

H2O
reaction ––(2)

(A) SN1, SN1 (B) SN1, SN2 (C) SN2, SN1 (D) SN1, no reaction
Br

NaI
7. acetone (A)

Type of reaction is
(A) SN1 (B) SN2 (C) E2 (D) E1

Cl CH3ONa
8. (A)
(50°C)
(A) SN1 (B) SN2 (C) E2 (D) E1
 Br
CH3OH
9.

(A) SN1 (B) SN2 (C) E2 (D) E1

10. Most reactive towards SN1

(A) Me – O – CH2 – Cl (B) Me – NH – CH2 – Cl
O
(C) Me – C – CH2 – Cl (D) Me – CH2 – CH2 – Cl

11. Most reactive towards SN1

Me

(A) Me – O – CH2 – CH3 (B) Me – CH 2 – O – CH – Me

Me

(C) Me – CH2 – O – C – Me (D) Me – O – C

Me

CH3 EtOH
(A)
low temp
C–Br
12.
CH3 EtOH (B)
high temp.
Type of mechanism of above reaction is
(A) A = SN1 B = SN2 (B) A = SN2 B = SN1
(C) A = SN1 B = E1 (D) A = E1 B = SN1

13. Which of following reaction is SN21

(A) R2 CuLi + H2C = CH – CH2 – Cl (B) RMgX + H2C = H2C – CH2 – Cl
14 14
(C) NaI + CH3 – Cl (D) Br EtOH
HBr
14. H2C = CH – CH2 – OH   (A) , Product (A) is -
14 SN11

14
(A) H2C = CH – CH2 – Br (B) H2 C = CH – CH2 – Br
14
14
(C) CH2 – CH = CH2 (D) CH 3 – CH – CH 2 – OH
|14 |
Br Br

Cl LiBr / DMSO
15.      ?
N S 2 conditions
Cl
The reaction outlined above should yield which of the following as its major product ?

Br Cl Br Cl
(A) (B) (C) (D)
Cl Br Br
16. Correct order of leaving group.

CH2 CH2
O O
(A) > (B) I <N N (C) CH3 – C – O < CH3 – S – O (D) All
O
NO2
17. Matrix
I

(A)
CH3OH (P) SN1 reaction

(B)
CH3O (Q) SN2 reaction

(C) KSH (R) E2 reaction

OH

(D) 14 SOCl2 (S) SNi reaction

18. Reactivity : Circle the reaction that reacts FASTER by SN2 in each pair :

(1) NaOCH3 (2) H O (3) NaOH

Cl   
 I  2
 Cl  

NaOCH3 NaOH NaOH

Br   I  
Cl

19. Encircle whichever of the following :

Br
|
(a) undergoes an SN2 reaction more rapidly, CH3 – Br or CH3 – CH – CH3
Br
|
(b) undergoes an SN1 reaction more rapidly, CH3–Br or CH – CH – CH
3 3

Br
(c) undergoes an SN2 reaction more rapidly, or
Br
(d) undergoes an SN1 reaction more rapidly, (CH3)3C – Br or (CH3)3C – I
Br
Br
(e) undergoes an SN1 reaction more rapidly, or
 Answer Key of DPP No.-39
1. D 2. D 3. A 4. A 5. D 6. D 7. B
8. B 9. A 10. B 11. D 12. C 13. A 14. B
15. B 16. D 17. A  P, B  R, C  Q, D  S

18. 3 (i) Br (ii) I (iii) Cl

Br Br
|
19. 5 (a) CH3–Br (b) CH3 – CH – CH3 (c) (d) (CH3)3C – I (e)
Br
 (A) SN1 (Substitution nucleophilic unimolecular)
TOTAL PRODUCTS
S.No. Compound Excluding Stereo isomer Including Stereo isomer

H2O/Acetone
Ph SN1
1.
Cl

Cl
H2O
2. SN1

EtOH
Ph – CH – CH2 — — OCH3
3. | SN1
Cl

R2
H2O
R1 Br
4. SN1
R3

CH3
H Cl H2O
5. H CH3 SN1
Ph

Cl H2O
6.
SN1

Cl
H2 O
7.
SN1

Et Cl
H2O
8.
SN1

CH3
H Cl H2O
9. D CH3 SN1
Ph

Cl

H2O
10.
SN1
O
 Answers Key -46
Excluding Stereo Including Stereo
1. 2 4
2. 2 3
3. 2 4
4. 1 2
5. 2 4
Excluding Stereo Including Stereo
6. 2 4
7. 2 3
8. 2 4
9. 2 6
10. 2 4