CPP FIITJEE ALKYL HALIDE

1. Which of the following statement is not correct?

(A) nucleophiles posses unshared pairs of electrons which are utilized in forming bonds with
electrophilic substrate
(B) The cyanide ions is an ambident nucleophile and caused nucleophilic substitution of alkyl
halides by either of its carbon atom or nitrogen atom
(C) The nitrite ions is an ambident nucleophile and causes nucleophilic substation of alkyl
halide by either of its oxygen atom or nitrogen atom
(D) strength of nucleophiles generally decreases on going down a group in the periodic table

2. Consider the following statement.

1. Bridgehead halide are inert to both SN1 and SN2 reactions.
2. The first step in both SN1 and E1 reactions is the same
3. SN2 reaction proceed with total retention of configuration
4. E2 eliminations are favored by the use of a solvent of low polarity and high concentration
of a strong base.
Which of the following above statement are correct?
(A) 1, 2 and 4 (B) 1 and 3 (C) 2, 3 and 4 (D) 1, 2, 3 and 4

3. Consider the following alcohols

CH2OH CH2OH CH2OH CH2OH

O 2N H2 N Br
(I) ( II ) ( III ) ( IV )
The order of decreasing relativities of these alcohols towards nucleohilic substation with HBr
is
(A) III > I > IV > II (B) III > I > II > IV (C) I > III > IV > II (D) I > III > II > IV

4. Consider the following nucleophiles

O O O
O
- - -
CF3 S O C 6H 5 S O CH3 C O
O O
(I) ( II ) ( III ) ( IV )
3
When attached to sp hybridised carbon there leaving group ability in nucleophilic
substitution reaction decreases in the order
(A) I > II > III > IV (B) I > II > IV > III (C) IV > I > II > III (D) IV > III > II > I

5. The reagent which reacts with I – chlorbutane to give a substitution product mainly is
(A) AlCl3 (B) KOH/MeOH
(C) NaCN (D) Mg/Et2O

6. The reaction of 4-bromobenzyl chloride with cyanide in ethanol leads to the formation of
(A) 4 – bromobenzyl cyanide (B) 4 – cyanobenzyl chloride
(C) 4 –cyanobenzyl cyanide (D) 4 – bromo – 2 – cyanobenzyl chloride.

7. Which one among the following carbocations has the lowest half-life

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 C
C
(A) (B)

C
CH3 C CH3
(C) (D)
CH3

8. Addition of KI accelerates the hydrolysis of primary alkyl halides because

(A) KI is soluble in organic solvents
(B) The iodide ions is a weak base and poor leaving group
(C) The iodide ion is a strong base
(D) The iodide ion is a powerful nucleophile as well as good leaving group

9. The compound which undergoes S N1 reaction most rapidly is

(A) Br (B) Br

(C) CH2Br (D) Br

10. Ethyl alcohol gives ethyl chloride on treatment with

(A) NaCl (B) Cl2 (C) SOCl2 (D) BeCl2

11. Consider the following sequence of reactions

HCl CH3C  CNa
  A  B
heat heat
The product B is

C C CH3
(A) (B) CH3CH  CH  C  C  CH3
(C) CH3CH2CH2C  CCH3 (D) CH3C  C  C  CH3

12. What is the order of reactivity of the following compounds towards nucleophilic substitution.

Cl Cl Cl

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

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 CH3

OH  aq
C2 H 5 Br  
13. C3 H 7
In the concentration of both the reactant is doubled than the rate if the reaction will
(A) remain unchanged (B) Reduce to the fourth
(C) quadruple (D) doubled

14. Which of the following will dehydrohalogenated most rapidly?

CH Cl Cl
(A) (B)
H2C CH2

Br
(C) (D) Br

15. Which of the following cannot undergo nucleophilic substitution under ordinary condition?
(A) allyl chloride (B) benzyl chloride (C) n-propyl chloride (D) vinyl chloride

AlCl3, 
16 (CH3)3 CCH2Cl X (predominant), X is
(A) (CH3)2 C CH2 CH3 (B) CH3 CH2 CH CH2 CH3
| |
Cl Cl
(C) CH3 CH2 CH2 CH2 CH2 Cl (D) none of the above.

Me Me Me
17 - -
HO HO
HO H H Cl B + H OH
(II) (I)

Et Et Et

(B) (A)

steps I and II are

(A) both SN1 (B) both SN2 (C) I: SN1, II: SN2 (D) I: SN2, II: SN1

II I
18. (CH3)3C CH = CH2 (CH3)3 C CH CH3 (CH3)2C = C (CH3)2
|
Cl
In this reaction
(A) I is E1, II is E2 (B) I is E2, II is E1 (C) both E1 (D) both E2

19. Major product of the following SN1 reaction is

_
CH3 – CH – CH – CH3 + O C2H5 
| |
Br CH
3

(A) CH3 – CH  CH – CH3 (B) CH3 – CH  CH2 CH2 OC2H5

| | |
OC2H5 CH3 CH3
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 CH3
|
(C) CH3 CH2 C CH 3 (D) none is correct.
|
OC2H5

CH3
|
20 CH3 – C Cl + C2H5ONa  Major product of this reaction is
|
CH3
CH3
|
(A) CH3 – C OC2H5 (B) CH3 – C  CH2
| |
CH3 CH
3

(C) CH3 – CH – CH2 OC2H5 (D) none is correct.

|
CH
3

21 Br2 / H2O
CH2 A, A is

CH2Br CH2OH
(A) (B)

OH Br
CH2Br CH3
(C) (D)

Br OH

22. Which of the following is most rapidly hydrolysed by SN1 mechanism?

(A) CH3 CH = CH Cl (B) Cl CH2 CH = CH2

(C) CH2Cl (D) (C6H5)3CCl

CH3
|
CH3CH2O-Na+, CH3CH2OH CH3CH2OH
23. (b) CH3 – C Br (a), (a) and (b) are
|
CH3
CH3 CH3
| |
(A) CH3 – C OCH2CH3 in both cases (B) CH3 – C  CH2 in both cases
|
CH3
CH3 CH3 CH3 CH3
| | | |
(C) CH3 – C OCH2CH3 and CH3 – C (D) CH3 – C and CH3 – C OCH2CH3
| || || |
CH3 CH2 CH2 CH3

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24 H3C CH3
Cl FeCl3
(A) , A is
CH3NO 2, 00C
CH3
CH3
H3C CH3
CH3
(A) (B)

CH3 CH2CH3

(C) both are correct (D) none is correct.

25. Which of the following compound has highest dipole moment?

(A) CH3 Cl (B) CH2 Cl2 (C) CH Cl3 (D) CCl4

26. Which of the following is an organometallic compound

(A) lithium methoxide (B) lithium acetate (C) lithium di methyl amide (D) methyl lithium.

27. Inversion of configuration is observed when the reaction proceeds through

(A) SN1 mechanism (B) E2 mechanism
(C) SN2 mechanism (D) Rearrangement

28. Cl CH2 CH2 CH2 – I + KCN  P (major), P is

(A) NC – CH2 CH2 CH2 – I (B) Cl – CH2 – CH2 CH2 CN
(C) CH2 = CH CH2 I (D) Cl CH2 CH = CH2

29. Which of the following alcohol will react most rapidly with H+?
H O
O
O
H3C
H3C CH3
CH3
OH
(I) (II) H
O O

OH H3C
H3C CH3
(iv)
(III)

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

30 CH3 Cl2/1 eq/h aq. KOH I2/NaOH

P P is

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 (A) Ph - CH (OI) CH3 (B) Ph CH3

COO
O
(C) CHI3 + (D) none

31. Which of the following free radical will be most stable?

CH3
CH3
CH3
H3C
CH H3C
CH
(I) (II)
CH3 CH3
CH3

H3C
H3C CH CH3
CH CH3
(III) (IV)

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

32. Which of the following alcohol shows fastest reaction with H+?
OH
OH
CH OH
(A) (B) EtOH (C) H2C (D)
CH2

33. Which of the following is most stable carbanion?

CHO CHO
H2 C H2C CHO H2C H2 C
Cl
(I) (II)
(III) (IV)

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

ANSWERS

1. D 2. A 3. A 4. B

5. C 6. A 7. D 8. D

9. C 10. C 11. C 12. B

13. D 14. D 15. D 16. A

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

21. A 22. D 23. A 24. B

25. A 26. D 27. C 28. B

29. A 30. C 31. B 32. D

33. A
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