IBCF-CHEM HALO DERIVATIVES Assignment by- Dr S B Sir (8077795180)

PART-1 MgBr

Q.1 Increasing order of electrophilic substitution for Q.6 ( 

 P, In the above reaction
i ) CO2
(ii) H3O
following compounds -
product 'P' is
CH3
CHO COOH

(I) (II)
(1) (2)

OCH3 CF3 OH
O
(III) (IV) (3) (4) C6H5–C–C6H5

(1) IV < I < II < III (2) III < II < I < IV Q.7 When CH3CH2CHCl2 is treated with NaNH2, the
(3) I < IV < III < II (4) II < III < I < IV product formed is :
(1) CH3–CH==CH2 (2) CH3–CCH
Q.2 In FCR, Toluene can be prepared by NH2 Cl
(3) CH3CH2CH (4) CH3CH2CH
(1) C6H6+CH3Cl (2) C6H5Cl+CH4 NH2 NH2
(3) C6H6+CH2Cl2 (4) C6H6+CH3COCl
Q.8 The correct order of reactivity towards the
electrophilic substitution of the compounds
Q.3 CH3–CH2–CH–CH3 , obtained by chlorination of aniline (I), benzene (II) and nitrobenzene (III) is
Cl
(1) III > II > I (2) II > III > I
n-butane, will be -
(3) I < II > III (4) I > II > III
(1) Meso form (2) Racemic mixture
Q.9 The treatment of benzene with isobutene in the
(3) d-form (4) -form presence of sulphuric acid gives
(1) Isobutyl benzene (2) t-butyl benzene
Q.4 An organic compound A(C4H9Cl) on reaction (3) n-Butyl benzene (4) No reaction

with Na/diethyl ether gives a hydrocarbon which Q.10 Which of the following compounds possesses the
C–H bond with the lowest bond dissociation
on monochlorination gives only one chloro
energy
derivative than, A is (1) Toluene. (2) Benzene
(1) t-butyl choride (2) Sec. butyl chloride (3) n-Pentane (4) 2, 2-Dimetyl propane

(3) Iso butyl chloride (4) n-butyl chloride Q.11 Among the following the most reactive towards
alcoholic KOH is
Q.5 Reactivity order of halides for dehydrohalogenation (1) CH2=CHBr (2) CH3COCH2CH2Br
(3) CH3CH2Br (4) CH3CH2CH2Br
is -
Q.12 Among the following, the one which reacts most
(1) R–F>R–Cl>R–Br>R–I
readily with ethanol is
(2) R–I>R–Br>R–Cl>R–F (1) p-nitro benzyl bromide
(2) p-chloro benzyl bromide
(3) R–I>R–Cl>R–Br>R–F
(3) p-methoxy benzyl bromide
(4) R–F>R–I>R–Br>R–Cl (4) p-methyl benzyl bromide
Q.13 Which of the following is least reactive in a
nucleophilic substitution reaction
(1) CH2=CHCl (2) CH3CH2Cl
ASSIGNMENT BY- DR S B SIR (8077795180) 11
IBCF-CHEM HALO DERIVATIVES Assignment by- Dr S B Sir (8077795180)

(3) CH2=CHCH2Cl (4) (CH3)3C–Cl

(1) Cl CH Cl
Q.14 The major product obtained on treatment of
CCl3
CH3CH2CH(F)CH3 with CH3O–/CH3OH is –
(1) CH3CH2CH(OCH3)CH3 Cl
(2) CH3CH=CHCH3
(2) Cl C Cl
(3) CH3CH2CH=CH2
(4) CH3CH2CH2CH2OCH3 CH2Cl

Q.15 Which of the following undergoes nucleophilic Cl

substitution exclusively by SN1 mechanism

(1) Ethyl choride (2) Isopropyl chloride

(3) Benzyl chloride (4) Chloro benzene
(3) Cl C Cl
Q.16 In a SN2 substitution reaction of the type H
R–Br + Cl DMF
 R–Cl + Br , which one
of the following has the highest relative rate ? OH
CH3 CH3 (4) Cl C Cl
(1) CH3–CH–CH2Br (2) CH3–C–CH2Br Cl

CH3 Q.20 In the following reaction

C6H5CH2Br   X,
1.Mg, Ether
(3) CH3–CH2Br (4) CH3–CH2–CH2Br 
2.H 3O

the product 'X' is -

Q.17 Which one of the following is most reactive
towards electrophilic attack ? (1) C6H5CH2OH
(2) C6H5CH3
NO2 OH (3) C6H5CH2CH2CH2C6H5
(1) (2) (4) C6H5CH2OCH2C6H5

Q.21 Which one is a nucleophilic substitution reaction

Cl CH2OH
among the following ?
(3) (4) (1) CH3CHO + HCN  CH3CH(OH)CN
H+ CH – CH – CH
(2) CH3–CH = CH2 + H2O 3 3
Q.18 Which of the following reactions is an example of
OH
nucleophilic substitution reaction ?
(3) RCHO + RMgX  R – CH – R
(1) RX + Mg  RMgX OH
(2) RX + KOH  ROH + KX CH3
(4) CH3 – CH2 – CH – CH2Br + NH3 
(3) 2RX + 2Na  R – R + 2NaX
CH3
(4) RX + H2  RH + HX CH3 – CH2 – CH – CH2NH2
Q.19 Trichloroacetaldehyde, CCl3CHO reacts with
chlorobenzene in presence of sulphuric acid and
produces -
Q.22 Which of the following compounds undergoes
nucleophilic substitution reaction most easily ?

ASSIGNMENT BY- DR S B SIR (8077795180) 2

IBCF-CHEM HALO DERIVATIVES Assignment by- Dr S B Sir (8077795180)
Cl Cl
(1) (2)
NO2
Cl Cl

(3) (4)
(CH3)2CH–CH2OC2H5 + Br–
CH3 OCH3 The mechanisms of reactions (i) and (ii) are
respectively :
Q.23 Consider the reactions : (1) SN 2 and S N1 (2) S N1 and SN 2
(i) (CH3)2CH–CH2Br  
 C2 H5OH
(3) S N1 and S N1 (4) SN 2 and SN 2
(CH3)2CH–CH2OC2H5 + HBr

(ii) (CH3)2CH–CH2Br C 
2H5O

PART-2

Q.1 Etheral solution of methyl iodide and ethyl iodide (3) HI > HCl < HF > HBr
in presence of metallic sodium gives - (4)HCl < HBr > HBr < HI
Q.6 Tertiary alkyl halides are practically inert to
(1) Methane (2) Propane
substitution by SN2 mechanism because of -
(3) Methanol (4) Propene
(1) instability (2) insolubility
Q.2 Which gives maximum yield of C2H5Cl (3) steric hindrance (4) inductive effect
Q.7 Alkyl halides react with dialkyl copper reagents
(1) C2H6 + Cl2  
 C2H5Cl + HCl
hv. light
to give -
(excess) (1) alkyl copper halides
(2) C2H6 + Cl2 light

hv
C2H5Cl + HCl (2) alkenes
(3) alkenyl halides
(excess) (4) alkanes
(3) C2H6 + Cl2 light

hv
C2H5Cl + HCl Q.8 Elimination of HBr from 2–bromobutane results
in the formation of –
(4) C2H6 + Cl2  C2H5Cl + HCl
Dark
(1) predominantly 2–butene
Q.3 The least reactive chlorine is present in - (2) equimolar mixture of 1 and 2–butene
(3) predominantly 2–butyne
(4) predominantly 1–butene
(1) Methyl chloride (2) Allyl chloride
(3) Ethyl chloride (4) Vinyl chloride Q.9 Among the following the one that gives positive
iodoform upon reaction with I2 and NaOH is –
Q.4 The reaction is a
(CH3)3 CBr + H2O  (CH3)3 COH + HBr
(1) C6H5CH2CH2OH
CH3
(1) Substitution reaction
(2) Debromination reaction (2) CH3–CHCH2OH
(3) Rearrangement reaction (3) PhCHOHCH3
(4) Elimination reaction (4) CH3CH2CH(OH)CH2CH3
Q.5 The correct order of the thermal stability of Q.10 Which of the following is the correct order of
hydrogen halides (H – X) is - decreasing SN2 reactivity ?
(1) HF > HCl > HBr > HI (1) RCH2X > R3CX > R2CHX
(2) HI > HBr > HCl > HF
ASSIGNMENT BY- DR S B SIR (8077795180) 33
IBCF-CHEM HALO DERIVATIVES Assignment by- Dr S B Sir (8077795180)

(2) RCH2X > R2CHX > R3CX CH3H CH3

(3) R3CX > R2CHX > RCH2X
(4) R2CHX > R3CX > RCH2X (A) MeO NO2
(X = a halogen)
H OHCH3
Q.11 The organic chloro compound, which shows
complete stereochemical inversion during a SN2 CH3H CH3
reaction , is -
(1) (CH3)3CCl (2) (CH3)2CHCl (B) MeO NO2
(3) CH3Cl (4) (C2H5)2CHCl
Q.12 The order of reactivity of the following alkyl OH H CH3
halides for a SN2 reaction is –
(1) RF > RCl > R–Br > R–I CH3H CH3
(2) R–F > R–Br > R–Cl > R–I
(3) R–Cl > R–Br > RF > RI (C) MeO NO2
(4) R–I > R–Br > R–Cl > R–F
Q.13 Identify the set of reagents/reaction conditions 'X' H CH3OH
and 'Y' in the following set of transformations
 Product
CH3CH2–CH2Br  CH3–CH–CH3
X Y (1) A & B (2) only B
Br (3) C only (4) A & C
(1) X = dilute aqueous NaOH, 20ºC ;
Y = HBr /acetic acid, 20ºC Q.16 The reagent in for the following conversion is/are
(2) X = concentrated alcoholic NaOH, 80ºC Br
?
Y = HBr/acetic acid, 20ºC Br H H
(3) X = dilute aqueous NaOH, 20ºC ;
Y = Br2/CHCl3, 0ºC (1) alcoholic KOH
(4) X = concentrated alcoholic NaOH, 80ºC (2) Alcholic KOH followed by NaNH2
Y = Br2/CHCl3, 0ºC
(3) aqueous KOH followed by NaNH2
Q.14 CH3MgBr (excess) + Ethyl ester  which can be
(4) Zn/CH3OH
formed as product.
CH2CH3 CH3

(1)HO CH2CH3 (2) HO CH2CH2CH3

Q.17 The major product of the following reaction is -
CH2CH3 CH2CH3
CH2CH3 CH3 Me Br
(3)HO CH2CH3 (4) HO CH3 
F PhSNa
?
CH3 CH3 Dimethylformamide
CH3 H CH3
NO2
Me Me SPh
Q.15 MeO NO2 SPh

F F
H Cl CH3
(1) (2)
on hydrolysis in presence of acetone ?
NO2 NO2

ASSIGNMENT BY- DR S B SIR (8077795180) 4

IBCF-CHEM HALO DERIVATIVES Assignment by- Dr S B Sir (8077795180)
Me Br Me SPh (1) 3 (2) 4 (3) 5 (4) 6
Q.20 By heating which mixture, propane nitrile will be
SPh SPh obtained ?
(3) (4) (1) Ethyl alcohol + KCN
(2) Propyl alcohol + KCN
NO2 NO2 (3) Ethyl chloride + KCN
(4) Propyl chloride + KCN
Q.18 Consider the following bromides
Q.21 Major product of the reaction
(CH3)3C – Cl + C2H5ONa 
would be -
(1) (CH3)2C–OC2H5 (2) (CH3)3C–C2H5
(3) (CH3)2C = CH2 (4) CH3–CH=CH–C2H5

C2H5Cl  3  'A'  
 'B'  
 'C'
NH C H Cl
2 5 2 5C H Cl
The correct order of S N 1 reactivity is Q.22
(1) A > B > C (2) B > C > A A, B and C respectively are -
(3) B > A > C (4) C > B > A (1) C2H5NH2, (C2H5)2NH, (C2H5)3N
(2) C2H5NH2, C2H5NH–Cl, C2H5–NCl2
Q.19 The total number of alkenes possible by (3) C2H5NH2, CH2=CH2, Cl–CH2–CH2–C2H5
dehydrobromination of 3-bromo-3 (4) C2H5NH2, (C2H5)3N, (C2H5)2NH
cyclopentylhexane using alcoholic KOH is.

ASSIGNMENT BY- DR S B SIR (8077795180) 55