Alkyl Halide Chemistry CAG

FIITJEE
003 Q20

1. Complete the following reactions

(I) H

CH 3 Br NaI / acetone
?
CH 3 OH

H
(II) Cl

NaI / acetone
?

2. The best leaving group is

(A) NH2  (B) OMe (C) Cl (D) Me

3. Which alkyl halide will give SN 2 reaction most easily?

(A) CH3 (B) CH3 Br
H3C C CH 2 Br H3 C C CH CH3
H3C H3C

(C) (D) CH3

Br
H3 C CH2 C Br
H3C CH CH3
CH3

4. Which alkylhalide will give SN1 reaction easily?

(A) CH3 (B) C2 H5
H3C C Br H3C C CH2 I

CH3 C3 H7

(C) Br (D) Ethyl iodide

H3C CH CH CH3
CH3

5. Arrange the following for reactivity order in SN 2

(I) 4 – bromo – 1, 1 – dimethyl cyclohexane
(II) 1 – bromo – 1, 4 – dimethyl cyclohexane
(III) 2 – bromo – 1, 3 – dimethyl cyclohexane
(A) (II) > (III) > (I) (B) (I) > (III) > (II) (C) (I) > (II) > (III) (D) none of these

6. Predict the product

O
ll
CH3-C-O-H

NH3
CH3–CH2–CH2–Mg–Br +
CH3SH

CH3  C  C  H

7. C6H5CH3 
Cl2
Fe
 A 
NBS
 B 
Mg
ether
 C 
ethylene
oxide 
 D Identify A, B, C and D.
H3O

FIITJEE CAG
 Alkyl Halide Chemistry CAG
FIITJEE
003 Q20

Mg / Et O
8. BrCH2CH2CHO 
2
 A   B, B is
H2O / acid, Heat

9. How are basicity and leaving group ability related?

(A) They are not related to each other.
(B) Good leaving groups are strong bases.
(C) Good leaving groups are weak bases.

10. What are the major products produced by heating the following isomeric alcohols with H2SO4 ?

11. What are the major products produced by heating the following isomeric alkyl bromides with NaOEt ?

12. The particular compound CH 3 is treated with methoxide ion. What could be correct regarding
this reaction?

Br
CH 3

(A) only elimination reaction will take place.

(B) only substitution reaction will take place
(C) ether formation will take place
(D) both elimination and substitution will take place

13. The decreasing order of reactivity of the compounds given below towards solvolysis under identical
conditions is
Cl Cl Cl Cl
H3C C CH 3 H3C C CH 3 H3C C CH3 H3C C CH 3

H3C H3C CH3

(IV)

(I) (II) (III)

(A) II > III > IV > I

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

FIITJEE CAG
 Alkyl Halide Chemistry CAG
FIITJEE
003 Q20

14. H Br
H3C D

H H AlC.KOH
A

Expected product of the reaction

(A) D (B) OH

H H3C D

(C) H3C (D) H C D

3

15. When 2-Bromo-2,3-dimethylbutane reacts with a base under E2 conditions, two alkenes (2,3-dimethyl-1-
butene and 2,3-dimethyl-2-butene) are formed. Which of the following bases would give the highest
percentage of 1-alkene?
(A) CH3 (B) CH3
- -
H3C C O H3C CH2 C O
CH3 CH2CH3
(C) H C - (D) CH3
3 CH2 O
-
H3C CH2 C O
CH3

16. Which of the following will not undergo aryne mechanism

(A) Me (B) Me Me (C)

Me Me Me Me
Me Me Br I
Br

17. Predict the number of products in following reactions.

(A) CH3 (B) CH3
Cl
KNH2 KNH2
Product(s) Product(s)
liq NH3 liq NH3
Cl
(C) CH3

KNH2
Product(s)
liq NH3

Cl

FIITJEE CAG
 Alkyl Halide Chemistry CAG
FIITJEE
003 Q20

18. Give the major elimination product obtained from an E2 reaction of each of the following alkyl halides with
hydroxide ion:
(a) CH3  CH
|
 CH2  CH3 (b) CH3  CH
|
 CH2  CH3
Cl F
CH3 CH3
| |

(c) CH3  CH CH

|
 CH2  CH3 (d) CH3  CH CH
|
 CH2  CH3
Cl F
(e) Br (f) Br

(g) CH3  CH
|
 CH2  CH  CH2
Cl

19. When 1-cyclohexylethanol is heated with aqueous HBr, the major product is 1-bromo-1- ethylcyclohexane.
Give a mechanism.

20. How will you convert these following

(A) H3C CH CH2 CH3 H3C CHBrCHBr CH3
OH

(B) OH

FIITJEE CAG
 Alkyl Halide Chemistry CAG
FIITJEE
003 Q20

Answers

1. (I) I (II) I
H3C H
H3C OH
H

2. –Cl

3. C

4. A

5. B

6. in all cases product is propane

7. CH3 CH 2Br

A= and o-isomer B=

Cl Cl
CH 2MgBr H2C CH 2 CH 2OH

C= D=

Cl Cl
O
||
OH
8. A  BrMgCH2CH2  C H
B=

9. C

10. in both cases CH3

11. CH3 CH3

and

12. B

13. D

14. C

FIITJEE CAG
 Alkyl Halide Chemistry CAG
FIITJEE
003 Q20

15. B

16. A, B, C

17. (a) CH3 CH3 (b) CH3

NH2

& & o & p-isomer

NH2 NH2
(c) CH3

& m-isomer

NH2

18. (a) CH3  CH  CH  CH3 (b) CH2  CH  CH2  CH3 (c)  CH3 2 C  CH  CH2  CH3
CH3
|

(d) CH3  C H  CH  CH  CH3 (e) (f)

(g) CH3  CH  CH  CH  CH2

FIITJEE CAG