QUIZ

ALKYL & ARYL HALIDES

FULL MARKS : TIME :

1. Neopentyl alcohol on treatment with HBr gives

a) Neopentyl bromide (b) 2-Bromo-2-methyl butane

c) 2-Methyl-2-butene (d) 2-Methyl-1-butene

2. Chlorine is most reactive towards NaOH in

a) CH 3Cl (b) CH 2 = CHCl (c) C6 H 5 Cl (d) C6 H 5 CH 2 Cl

3. A halide with formula C6 H 13 Br gave two isomeric alkenes A and B with formula C6 H 12 .
On reductive ozonolyis of mixture of A and B following compounds were obtained.
CH 3COCH 3 , CH 3CHO, CH 3CH 2 CHO and (CH 3 ) 2 CHCHO. The halide is

a) 2-bromohexane (b) 3-bromo-2-methyl pentane (c) 2-2-dimethyl-1-bromohexane (d) None

4. Which chloro derivative of benzene among the following would undergo hydrolysis most
readily with aqueous NaOH to furnish the corresponding hydroxy derivative?

a) NO2 Cl (b)

c) (d)

5. Isobutyl magnesium bromide with dry ether and absolute alcohol gives

a) (b)

c) (d)
 -2-

6. Tertiary pentyl alcohol on heating with KI and H 2 SO4 produces.

a) Tertiary pentyl chloride (b) 2-chloro-2-methyl butane

c) Isopentyl chloride (d) 2-methyl-2-butene

7. Which of the following is the correct order of increasing order of easiness of leaving group

a) R −  CH 3O −  OH −  CN −  CH 3COO −  C6 H 5 SO2 O −
b) CH 3O −  R −  CH 3COO −  CN −  OH −  C6 H 5 SO2 O −
c) R −  CH 3O −  CH 3COO −  CN −  C6 H 5 SO2 O −  OH −
d) None

8. Which of the following statements are correct for SN 2 reaction

a) CH 2 Cl is faster than Cl

b) I is faster than Cl

c) I is faster than
Cl
d) All are correct

9. An SN 2 reaction at any asymmetric carbon of a compound always gives

a) an enantiomer of the substrate (b) A product with opposite optical rotation

c) A mixture of diastereomers (d) a single isomer.

10. The rate of SN 1 reaction is fastest in solvents

a) Water (b) Alcohol (c) Acetone (d) Acetic acid (e) All

11. In the given reaction

H Br
NaI
H3C [X]
acetone
C2H5
[X] will be

H I H CH3
(a) H3C (b) I
C2 H5 C2 H5
H3C
(c) Mixture of (a) and (b) (d)
CH3
12. In the given reaction
CH3

H OH TsCl / Pyridine
[X]
H OH

CH3
[X] will be:

CH3 CH3 CH3

H O H OT s H
Ts O
H OH H OT s H

CH3 CH3 CH3 no reaction

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

13. In the given reaction

O
H+
OH [X]

[X] will be:

OH
OH OH
(a) (b)

OH OH

(c) (d)
O OH
OH
14. In the given reaction
Cl
Cl
CH3OH
[X]

O Cl
(excess)

Cl OCH3
Cl Cl
(a) (b)

O OCH3 O OCH3
Cl OCH3
OCH3 Cl
(c) (d)

O Cl O Cl

15. In the given reaction

TsO
CH3

H3C
(i) SH (one equivalent)
OTs [X]
(ii) KOH
[X] will be:

(a) OTs (b)

S
H3C
H3C

CH3
CH3
S
S
(c) CH3 (d) CH3

S S

CH3 CH3
16. Identify product D of the below mentioned reaction:
conc. NBS KCN H3O+
A B C D
OH H2SO4

(a) O (b) CH3

OH O

CH3 OH
(c) O (d) OH

OH O

O
CH3

OH

17. HO
Cl
OH
A A has maximum reactivity, A is ………

Cl

(a) Br (b) I

Cl Cl Cl Cl
(c) Cl (d) SO3 H

Cl Cl Cl Cl

18. Cl Cl
H3C CH
3 2
C
3 CH2
1
Cl CH CH2
2 1
(I) (II)

On addition of HOBr to (I) and (II), we get

(a) Br at C2 in both cases (b) Br at C2 in II and at C1 in I
(c) Br at C2 in I and at C1 in II (d) None of the above
19. Cl

OEt-
* The prouduct is
O

(a) Cl (b) Cl
* *
HO OEt EtO OH
(c) EtO (d) OEt
*

*
O O

Br  
20. A & Br ONa B
ONa
A and B are

O O
(a) O O & (b) O &

O
Br O CH3 n &
(c) O & O O (d)
O CH3
Br n

21. Cl

OEt-
* The prouduct is
O

(a) Cl (b) Cl
* *
HO OEt EtO OH
(c) OEt (d) EtO
*

*
O O
22. Identify the set of reagents/reaction conditions ‘X’ and ‘Y’ in the following set of
transformations.
H3C CH3
X Y
Product H3C
Br
Br
(A) X = dilute aqueous NaOH, 20°C; Y = HBr/acetic acid 20°C
(B) X = concentrated alcoholic NaOH, 80°C; Y = HBr/acetic acid 20°C
(C) X = dilute aqueous NaOH, 20°C; Y = Br2/CHCl3, 0°C
(D) X = concentrated alcoholic NaOH, 80°C; Y = Br2/CHCl, 0°C

23. Which of the following alcohols can be prepared by the action of a suitable Grignard
regent on an aldehyde or ketone followed by hydrolysis?
(a) Ethyl alcohol (b) Methanol
(c) Isopropyl alcohol (d) n-propyl alcohol

24 Identify product D of the below mentioned reaction:

conc. NBS KCN H3O+
A B C D
OH H2SO4

(a) O (b) CH3

OH O

CH3 OH
(c) O (d) OH

OH O

O
CH3

OH

25. on reaction with TsCl in acidic medium and then on reduction with
OH LiAlH4 forms

(a) (b) OTs

(c) (d) None of the above

26. Br

(i) Mg/ether
is reacted with
O (ii) CO2
(iii) H3O+
CH3 O
The final product is

(a) O OH (b) MgBr

CH3 H3C
O O

(c) O OH (d) None of the above

H3C

27.
is reacted with the following compounds in presence of AlCl3.

(i) O (ii) Cl
CH3
H3C S O

O
CH3
(iii) O (iv) Br
F3 C S O CH3

O
CH3
The correct order of reactivity is
(a) (i) > (iii) > (iv) > (ii) (b) (i) > (iii) > (ii) > (iv)
(c) (iii) > (i) > (iv) > (ii) (d) None of the above

28. The rate of hydrolysis of following compounds follows the order:

(i) CH3CH==CHCl (ii) ClCH2CH==CH2
(iii) Ph—CH2Cl (iv) Ph3CCl

(a) (i) > (ii) > (iii) > (iv) (b) (iv) > (iii) > (ii) > (i)
(c) (iii) > (iv) > (ii) > (i) (d) (ii) > (i) > (iv) > (iii)
29. A will give by E1 reaction.
Br
A

(a) CH2 (b) CH3

(c) CH2 (d) CH2

30. Which of the following react with water?

(a) CHCl3 (b) Cl3CCHO (c) CCl4 (d) ClCH2CH2Cl