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DPP- REACTION MECHANISM:SN1 AND SN2

1. Which one of the following has maximum nucleophilicity?
CH 3
 

|
(a) C H 3 (b) NH2 (c) CH3O (d) CH  C  O 
3
|
CH 3
2. Which one of the following has maximum nucleophilicity ?

(a) CH3S (b) C6H5 – O (c) Et3N (d) F

3. Correct arrangement of the following nucleophiles in the order of their nucleophilic strength is–
(a) C6H5O < CH3O < CH3COO < OH (b) CH3COO < C6H5O < CH3O < OH
   
(c) C6H5O < CH3COO < CH3O < OH (d) CH3COO < C6H5O < OH < CH3O

4. Decreasing order of relative nucleophilicity of the following nucleophiles in protic solvent is –

       
(a) SH  Ac O  Ph O  O H  H 2O (b) SH  O H  Ph O  Ac O  H 2 O
       
(c) SH  Ph O  O H  H 2 O  Ac O (d) O H  SH  Ph O  Ac O  H 2O

5. CH2-x CH2 CN


NaCN


In the given reaction rate is fastest, when (X) is :

O O
|| ||
(a) – OH (b) – NH2 (c) S  OCH 3 (d) O  S  CH 3
|| ||
O O
6. Which of the following is not expected to be intermediate of the following reaction ?
OH
I


H2O



 OH2
 

(a) (b) (c) (d)

7. What will be the major product of the following reaction?

H CH 3
| | CH3OH,30 C
CH 3  C  C  CH  CH 3  
| | |
H CH 3Br
H CH 3 CH 3 H CH 3 OCH3
| | | | | |
(a) CH  C  C  C  CH (b) CH  C  C  C  CH 3
3 3 3
| | | | | |
OCH 3 H H H CH 3 H

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H CH3 CH3 H CH 3 H
| | | | | |
(c) CH3  C  C  C  CH3 (d) CH3  C  C  C  CH 2
| | | | | | |
H OCH3H H CH 3 H OCH 3

8. Which one of the following compounds will give (d) and (l) form in SN1 reaction (as major product)
CH 3 H C2H5 H
| | | |
(a) CH3  C  Br (b) CH  C  Br (c) CH  C  Br (d) CH  CH  C  Br
3 3 3
| | | | |
CH 3 C2 H 5 C2H5 CH 3 CH 3
9. Which of the following will be most reactive for SN1 reaction ?
OH

OH
OH
CH OH |
(a) (b) | (c) CH  C  CH (d)
3 3
C6 H 5  CH  C 6 H 5 |
CH 3
10. Which describes the best stereochemical aspects of the following reaction ?
H3 C
H  Br
Et   Product
Ph
OH
(a) Inversion of configuration occurs at the carbon undergoing substitution.
(b) Retention of configuration occurs at the carbon undergoing substitution.
(c) Racemization occurs at the carbon undergoing substitution.
(d) The carbon undergoing substitution is not stereogenic.

11. CH3
D 
HI
 product
OH

Identify the major product

CH3
I
I D D D
I
(a) D (b) (c) I (d)

12. Br


H 2 O/Acetone
 (A); Product (A) is :

Br
Br OH OH
OH

(a) OH (b) OH (c) (d) Br


13. When the concentration of alkyl halide is tripled and the concentration of O H ion is reduced to
half, the rate of SN2 reaction increase by :
(a) 3 times (b) 2 times (c) 1.5 times (d) 6 times
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14. The decreasing order of rate of SN2 reaction is :

CH 3  C  CH 2  Cl CH 3  CH  CH 2  Cl
CH3 – Cl || | CH3 CH2 Cl
O CH 3
(i) (ii) (iii) (iv)
(a) IV > III > II > I (b) II > III > I > IV (c) II > I > IV > III (d) none

CH3(CH2)2 – CH2OH   X,NaBr,H SO

15. 2 4

Identify X and the mechanism of the reaction

(a) CH3 – CH2 – CH2 – CH2 – Br & SN1 (b) CH3 – CH2 – CH2 – CH2 – Br & SN2

CH 3  CH  CH 2  CH 3 &SN 1 CH 3  CH  CH 2  CH 3 &SN 2
(c) | (d) |
Br Br

16. In the given reaction : CH3 – CH2 – CH2 – O – CH2 – CH3 
HCl
[X] + [Y]

[X] and [Y] will respectively be :

(a) CH3 – CH2 – CH2 OH & CH3 – CH2 – Cl (b) CH3 – CH2 – CH2 – Cl & CH3 – CH2 – OH

(c) CH3 – CH2 – CH2 – Cl & CH2 = CH2 (d) CH3 – CH = CH2 & CH2 = CH2

17. Which one is the strongents nucleiphilic site in the following species ?
O O
4
 CH3
1O
 3

O S
O O
O2


(a) 1 (b) 2 (c) 3 (d) 4

18. SN1 reaction undergoes through a carbocation intermediate as follows :-

R – X (aq.) R+ (aq.) + X- (aq.)   ROH (aq.) + H+ (aq.)
H2O
fast
[R = t – Bu, iso – Pr, Et, Me] (X = Cl, Br, I)
The correct statements are
(i) The decreasing order of rate of SN1 reaction is t – BuX > iso – PrX > EtX > MeX
(ii) The decreasing order of ionization energy is MeX > EtX > iso – PrX > t – BuX
(iii) The decreasing order of energy of activation is t – BuX > iso – PrX > EtX > MeX

(a) I & II are correct (b) I & III are correct (c) II and III are correct (d) I, II & III are correct
ANSWER KEY
1(a) 2(a) 3(d) 4(b) 5(d) 6(a)

7(c) 8(b) 9(d) 10(c) 11(a) 12(a)

13(c) 14(c) 15(b) 16(a) 17(d) 18(a)

ALIGANJ/ AASHIYANA/ Hazratganj, Lucknow- 7231912196