Halogen Derivatives

(Choose the correct option. One or more than one are correct)

Q.1 Which are possible products in following

moist Ag O


2


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

Q.2 SN1 & SN2 is not favourable in

(A) H2C = CH–Cl (B) Ph–CH2–Cl (C) Ph–Cl (D) H2C=CH–CH2–Cl

Q.3 SN1 & SN2 product are same in (excluding stereoisomer)

(A) (B) (C) (D) Ph  CH  CH  CH 3

| |
CH 3 Cl

Q.4 Which of the following statements is / are true?

(A) CH3–CH2–CH2–I will react more readily than (CH3)2 CHI for SN2 reactions.
(B) CH3–CH2–CH2–Cl will react more readily than CH3–CH2–CH2–Br for SN2 reaction.
(C) CH3–CH2–CH2–CH2–Br will react more readily than (CH3)3C–CH2–Br for SN2 reactions
(D) CH3–O–C6H4– CH2Br will react more readily than NO2–C6H5–CH2Br for SN2 reaction

Q.5 A solution of (R)-2-iodobutane, [] = –15.9° in acetone is treated with radioactive iodied, until 1.0% of
iodobutane contain radioactive iodine, the specific rotation of recovered iodobutane is found to be
–15.58°, which statement is correct about above information.
(A) It has optical purity 96% (B) % of R in solution is 99%
(C) Racemic mixture is 2% (D) Final solution is dextrorotatory

Q.6 In which of the following case configuration about chiral C* is retained:

SOCl CH ONa
(A) 
Na
3
CH Br
(B) 2  3


(C) 
PCl
3  3
CH ONa
(D) H/ 

MeOH

Q.7 Which of the following will react with AcOAg

(A) R–NH2 (B) R–OTs (C) R–N3 (D) R–Br

Halogen Derivatives [14]

Q.8 Consider the given reaction
CH 3
|
H  C  OTs NaCN
 CH 3CH 2CH  CN
|
C 2 H 5 (S) |
CH 3
which of following statements are correct for above reaction.
(A) Product formation takes place due to the breaking of O–Ts
(B) The reaction is S 2
N
(C) The reaction is S
N1
(D) Configuration of product is (R)

Q.9 Benzoyl chloride is less reactive than acetyl chloride for nucleophilic acyl substitution reaction because
O
||
(A)  C  group of benzoyl chloride is in conjugation with benzene ring. This makes benzoyl chloride
more stable than acetylchloride.
( B )

3– group of acetyl chloride make C–Cl bond stronger due to the +I effect.
C H

(C) C6H5– group of benzoyl chloride make C–Cl bond weaker due to +R effect.
(D) Carbonyl carbon in benzoyl chloride is less electron deficient than acetyl chloride

Q.10 SN2 reaction will be negligible in

Br

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

Q.11 Rate of SN2 depends on

(A) Conc of Nucleophile (B) Conc of substrate
(C) Nature of leaving group (D) Nature of solvent

Q.12 Correct statement(s) for the product(s) of following reaction.

CH2 = CH – CH2 – Ph Cl  
/ 500C
2
(A) Four different products are formed
(B) Two optically active products are formed
(C) The optically active compound formed here can also be made by the reaction of HCl
(D) The reaction path is free radical substitution.
Q.13 In the given pair in which pair the first compound is more reactive than second to SN2 reaction.

Cl
(A) Cl CH2Cl (B)
Cl

Cl Cl

(C) (D)
Cl Cl

Halogen Derivatives [15]

Q.14 A gem dichloride is formed in the reaction :
(A) CH3CHO and PCl5 (B) CH3COCH3 and PCl5
(C) CH2 = CH2 and Cl2 (D) CH2 = CHCl and HCl

Q.15 Incorrect about alkyl halides is / are:

(A) Tertiary alkyl halides undergo SN2 substitutions
(B) Alkyl iodides on exposure to sunlight gradually darken
(C) Alkyl chlorides do not give beilstein test
(D) A nucleophilic substitution is most difficult in alkyl iodides

Q.16 Which of the following statement is / are correct ?

(A) Carbonyl compounds of the general structure CH  C  R give a positive iodoform test
3
||
O
(B) All secondary alcohols give iodoform reaction
(C) Alkanols of the structure CH3CH(OH) – R (where R = H, alkyl or aryl) give iodoform reaction.
(D) The only aldehyde giving iodoform reaction is acetaldehyde.

Q.17 Match List I with List II and select the correct answer from the codes given below:
List I List II

(A) CH3–O–SO2CH3 + C 2 H 5 O (1) CH3–CH2–PH2
(B) CH3–CH2–I + PH3 (2) CH3–O–C2H5
 
(C) HC  C Na + CH3–CH2–Br (3) CH3–O–CH3

(D) CH3–Cl + CH3– O (4) CHC–CH2–CH3

Q.18 Match List-I with List-II for given S reaction & select the correct answer from the codes given below
N2

Z–CH2Br + CH3 O  Z–CH2–OCH3 + Br
List-I List-II (relative reactivity)
(A) H– (P) 0.1
(B) CH3– (Q) 3
(C) C2H5– (R) 1

(D) (S) 100

Q.19 In which product formation takes place according to Hoffmann's rule

 
t B u O K CH3CH 2 O K
(A) CH 3CH 2  CH  CH 3   (B) CH 3CH 2  CH  CH 3   
 
| |
Br Br

 
(C) O
H
 (D) CH 3CH 2CH  CH 3 O
H

 
|

S(CH 3 ) 2

Halogen Derivatives [16]

Q.20 Which of following will give syn-elimination
(A) CH3CH2CH2–OCOCH3 (B) CH 3CH 2CH  CH 3
|
Cl
CH 3
| 
(C) CH 3CH 2CH 2  O  C  S  CH 3 (D) CH 3CH 2CH 2 N  O
|| |
S CH 3

Q.21 Which of following are correct for given reaction




(A) Major product of reaction is (B) Major product is

(C) The reaction is thermal elimination reaction (D) The reaction is E2 reaction

Q.22 Which alkyl halide undergo E2 elimination

(A) (B)

(C) (D)

Q.23 Match the List I (reaction) with List II (reaction intermediate) and select the correct answer using the
codes given below the Lists.
List I List II
(A) CF3–CHCl2 alc /
.KOH

  CF2 = CCl2 (1) Transition state only

CH 3
| 
(B) CH  C  OH H
 CH 3  C  CH 2 (2) Carbocation
3
| |
CH 3 CH 3

(C) CH3–CH2–Br   CH2=CH2

alc.KOH
(3) Carbanion


Br
|
(D) CH 3  C  CH 3 aq
. KOH
 /
 CH 3  C  CH 2 (4) Free radical
| |
CH 3 CH 3

Halogen Derivatives [17]

Q.24 Match the List I with List II and select the correct answer using the codes given below the Lists.
List I List II
(A) E1CB (1) 3° Amine oxide
(B) Saytzeff alkene as major product (2) Xanthate
Cl
|
(C) E2 (3) CH 3  CH 2  CH  CH 3

(D) Ei (4) C 6 H 5  CH 2  CH  CH 3
|
F

Q.25 Match the following

List-I List-II


CH CH O
(A) 3 

2 (P) E1



CH3CH 2 O
(B)   
 (Q) E2
CH3CH 2OD

Ag O
(C) 
2
 (R) E1cb
moist

(D) alc
. KOH
 (S) Ei

Halogen Derivatives [18]

 ANSWER KEY

Q.1 A,B Q.2 A,C Q.3 B,C Q.4 A,C

Q.5 B,C Q.6 A,C Q.7 B,C,D Q.8 B,D
Q.9 D Q.10 A,B,C Q.11 A,B,C,D Q.12 A,B,D
Q.13 B,D Q.14 A,B,D Q.15 A,C,D Q.16 A,C,D
Q.17 (A) 2 ; (B) 1 ; (C) 4 ; (D) 3 Q.18 (A) S ; (B) Q ; (C) R ; (D) P
Q.19 A,C,D Q.20 A,C,D Q.21 A,C Q.22 A,B
Q.23 (A) 3 ; (B) 2 ; (C) 1 ; (D) 2 Q.24 (A) 4 ; (B) 3, 4 ; (C) 3 ; (D) 1, 2
Q.25 (A) Q ; (B) R ; (C) P ; (D) Q

Halogen Derivatives [26]