CPP FIITJEE ALKYL HALIDE

Single Correct Choice Type

1. Which of the following is not expected to be intermediate of the following reaction?

OH
I
H2 O

(A) (B)

OH2

(C) (D)

CH3

Br H
 NaI  product; SN 2 product of the reaction is
Acetone
2. H CH3

CH2 - CH3
CH3 CH3

I H H I
(A) (B)
H CH3 H CH3

CH2 - CH3 CH2 - CH3

CH3 CH3

I CH3 I H
(C) (D)
H CH3 CH3 H

CH2 - CH3 CH2 - CH3

3. Rate of SN2 will be negligible in:

Br Br

(A) (B)
 Br Br

(C) (D)

4. What is the major product obtained in the following reaction?

CH2 - Br
NH3
  product
EtOH
Br
CH2 - NH 2 CH2 - Br

(A) (B)
Br NH2

CH2 - NH 2 CH2 - NH 2

(C) (D)
NH2

5. H Acetone
F  NaI 1 mole    A  ; Major product of this reaction is :
 major 
Br H
(A) H F (B) I F
I H H H

(C) H I (D) H
H
Br H Br I

6. Which of the following alkyhalide undergo rearrangement in SN1 reaction?

CH3 Cl

(A) CH3 - C - CH - CH3 (B)

CH3 I CH3

I
(C) (D) All of these

7. Arrange the following three chlorides in decreasing order towards SN1 reactivity.
(1)
Cl (2) (3)
Cl Cl
(A) 1 > 2 > 3 (B) 2 > 3 > 1
(C) 2 > 1 > 3 (D) 3 > 2 > 1
8. Which compound undergoes nucleophilic substitution with NaCN at the fastest rate?

Br
(A) Br (B)

Br
(C) Br (D)

9. Rank the following in order of decreasing rate of solvolysis with aqueous ethanol (fastest 
slowest).
CH3 CH3 Br
H2C = C - Br Br CH3 - CHCH2CH(CH3)2
(1) (2) (3)
(A) 2 > 1 > 3 (B) 1 > 2 > 3
(C) 2 > 3 > 1 (D) 1 > 3 > 2

10. The reaction of 4-bromobenzyl chloride with sodium 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

11. Which of the following reactant will not favour nucleophilic substitution reaction?

(A) (B) Ph – Br

Br

CH3
(C) CH3 - C - CH2 - Br (D) All the above
CH3

14
C labelled

12. OTs
RCO2H
  product; Pr oduct of this reaction is
no label

OCOR OCOR
(A) (B)

(C) Both A & B (D) None of these

 OH

13.
TsCl LiAlH4

Pyridine
 A    B  ; Pr oduct B  of this reaction is

(A) (B)

Cl

(C) (D)

14. Which of the following is most reactive towards SN2 reaction?

Cl
Cl

(A) (B)

CH3

Cl Cl

(C) (D)

Cl NO2

15 The reaction
H OH H Cl
SOCl2 SO2 HCl

Proceeds by the ……………..mechanism

(A) SNi (B) SN2
(C) SE2 (D) SN1

16 Consider the following anions

O O O O
CF3 - S - O C6 H5 - S - O CH3 -C - O
O O
(I) (II) (III) (IV)
When attached to sp3- hybridized carbon, their 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
 CH3

SO2Cl2 NBS KSH


h
  A    B     C  , Pr oduct B  is :
17.

SH SH

(A) (B)
Br Cl

Br Br

(C) (D)
SH

18 Br2 /h Alcoholic HBr

  Major  x  
KOH/ 
 Major  Y  
Peroxide
 Major  Z 

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

Br

CH3

NBS  2 mole  KCN

19  A  
1 mole   
  B , Pr oduct B  is :

CH2 - CH3
Br CN CN

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

CN Br
20. The decreasing order of reactivity of the compounds given below towards solvolysis under
identical conditions is:
Cl Cl Cl

CH3 - C - CH3 CH3 - C - CH3 CH3 - C - CH3

Cl

CH3 - C - CH3

H3C CH3 CH3

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

OH

21.
H2SO4
  A
 Major 

Major product A is:

(A) (B)

(C) (D)

Ph
OH
H3PO4
22.   Major product obtained by dehydration of given alcohol


is:

Ph Ph

(A) (B)

Ph Ph

(C) (D)

23. Out of the following which is polar aprotic solvent?

CH3

(A) S=O (B) CH3CH2OH

CH3
 COOH CH3 C CH3
(C) (D)
COOH OH

24. Out of the following which is correct order of nucleophillicity in polar aprotic solvent?
       
(A) F  Cl  Br  I (B) I  Br  Cl  F
       
(C) Br  Cl  I  F (D) Cl  Br  F  I

25. Out of the following which don’t show SN2, E2, SN1 & E1 reaction?
CH2Cl Cl

(A) (B)

CH3 Cl
Cl
(C) (D)

26. In which of the following reaction resonance stabilized product will form:
CH2 - OH OH
H
  H
(A)  (B)  


CH3

(C) OH H
(D) All of these
 


27. Which of the following is least reactive towards nucleophilic substitution with aqueous KOH?
Cl Cl

(A) (B)

NO2 OH
Cl Br
NO2

(C) (D)

NO2 NO2

28. Which of the following will give acetophenone as a product?

CH3COCl
 
 CH3CO2 O
(A) AlCl3 (B) 
AlCl3

 Cl
aq.KOH
C - CH3 
(C)  (D) All the above
Cl

29. Best method of preparing alkyl halide is:-

(A) ROH  SOCl2  (B) ROH  PCl5 
anhy.ZnCl
(C) ROH  PCl3  (D) ROH  HCl 
2


30. CH3

NaOEt
  Major product of the reaction is:
E2 reaction
Cl

CH3 CH3

(A) (B)

CH3 CH3

(C) (D)

31. Arrange the following compounds in decreasing order of reactivity towards nucleophilic
substitution reaction through bimolecular mechanism.
Cl O O O

Cl

O O Cl O

(I) (II) (III)

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

32. Arrange the following compounds in decreasing order of reactivity through SN1
mechanism?
 CH3 3 CCl  C2H5 3 CCl Ph3CCl
I II III
(A) I > II > III (B) II > I > III
(C) III > II > I (D) III > I > II
33. OH

OH
 i NaOH 1eq  X
  
 ii CH3Br

Product(X) in the above reaction is:

OH OMe

OMe OH
(A) (B)

OMe OH

(C) (D)

34. Which of the following compounds will not undergo elimination reaction in presence of
C2H5ONa and C2H5OH in normal conditions?
CH3 CH3

Br Br
(A) (B)

CH3 CH3
CH3 CH3

Br Br
(C) (D)

CH3 CH3

35. CH2Br
KCN H2 / Pt
  X   Y
C2H5 OH
Br
Product(Y) in the above reaction is:
CH2CN CH2CH2NH2

(A) (B)
CN CN
CH2CH2NH2 CH2CH2NH2

(C) (D)
CH2NH2 Br

36. H Br
CH3 D

H alc.KOH
H  Pr oduct

The major organic product obtained in the above reaction is:

 OH
D
CH3 D
(A) (B)

CH3 D

(C) (D) H

Section – II (More than one option may be correct)

37. Cl
OH
NaOH


X X
In the above reaction, ‘X’ can be
(A) NO2 (B) N2
(C) CH3 (D) CN

38. Which of the following graph(s) represent(s) SN2 reaction?

(A) rate (B) rate

CH3Br C2H5Br (CH3)2CHBr (CH3)3CBr CH3 I CH3Br CH3CI CH3F

rate
(C) rate (D)

CH3Br C2H5Br (CH3)2CHBr (CH3)3CBr CH3F CH3Cl CH3Br CH3 I

39. Which of the following compound(s) is/are more reactive than C2H5Cl towards hydrolysis by
SN2 mechanism under identical conditions?
(A) C2H5Br (B) CH3CH2CH2Cl
(C) CH3Br (D) CH3Cl

40. Which of the following compound(s) react(s) with HCl to form benzyl chloride?
CH2OH CH2NH2

(A) (B)

CH2CN CH2OCH3

(C) (D)
41. Which of the following compound(s) react(s) with Zn to form cyclic compound(s)?
CH3CHCH2CH2CH2CH2 Cl
(A) CI  CH2 CH2CH2CH2 CH2CH2  CI (B)
Cl
CH3CH2CHCH2CH2CH2Cl CH3CH2CH2CHCH2CH2Cl
(C) (D)
Cl Cl

Subjective type
X
E2 reaction
42.  

(Hoffmann product) (Saytzeff product)

(i) In the above reaction, maximum saytzeff produce will obtained when:
(A) X = – I (B) X = – Cl
(C) X = – Br (D) X = – F
(ii) In the above reaction, Hoffmann product is major when X is:
(A) – I (B) – Cl
(C) – Br (D) – F

43. Find missing species A and B

AgCN Reduction
(i) RX  ' A '  RNC (ii) C2H5Br   ' A '   'B '

44. Write major product with the proper mechanism

(i)Br2 ,h
C6H5 C2H5 
(ii)NaCN


45. Chloromethane reacts with KCN to form Ethan nitrile as main product and with AgCN to form
methyl isocyanide as main product. Why?

46. Convert CH3  CH  CH2 int oCH3CH2CH2I

Br O
47. Compound undergoes intramolecular nucleophilic substitution of the
type ………… giving ……………..

48. Explain the following:

(i) Ethyl bromide reacts with KNO2 to yield a mixture of two isomeric substitution products.
(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
(iii) Chlorobenzene is unreactive towards SN reaction.

PI3 KCN Hydrolysis

49. CH3 OH    A    B    C

Numerical Type

50. CH3

2 5 C H O
CH3 CH CH CH CH3   Pr oducts
H2O
Ph Cl
How many alkenes are formed in the above elimination reaction if we consider that reaction
passes through E1 path (without differentiating between optical isomers)?
51. CH3

2 5 C H O
CH3 CH CH CH CH3   Pr oducts
H2O
Ph Cl
How many alkenes are formed in the above elimination reaction if we consider that reaction
passes through E1 path (without considering stereoisomers )?

52. I

I
 NBS H2O
   X     Y    products
Zn

How many possible monohydric alcohols are formed in the above reaction?

ANSWERS
1. A 2. B 3. C 4. A
5. B 6. D 7. B 8. A
9. C 10. A 11. D 12. C
13. C 14. D 15 A 16 B
17. B 18. C 19. B 20. D
21. C 22. C 23. A 24. A
25. D 26. D 27. B 28. D
29. A 30. B 31. C 32. D
33. B 34. B 35. D 36. C
37. A 38. AD 39. ACD 40. ABD
41. ABCD
42. (i) A (ii) D
43. (i) AgCN
(ii) C2H5NC, C2H5NHCH3

NC CH CH3

44.

46. (i) HBr, ROOR, (ii) P + I2 47. SN2, Pyron

48. Hint:
(i) SN1 reaction
(ii) Hybridization of C in chlorobenzene is SP2
(iii) It does not undergo either SN1 or SN2 mechanism
49. CH3I, CH3CN, CH3COOH 50. 7 51. 5 52. 3