EXERCISES

SECTION A: TOPICWISE QUESTIONS

5. Which of the following halide is 2°?

Methods of Preparatlon of Haloalkanes, Nomenclature,
Structure of Haloalkane (a) Isopropyl chloride (b) Isobutyl chloride
(c) n-propyl chloride (d) n-butyl chloride
1. CH Cl +AgF C,HF +AgCI 6. Benzene hexachloride is
The above reaction is called (a) 1,2, 3,4, 5, 6-hexachlorocyclohexane
(a) Hunsdiecker (b) Swart (b) 1, 1, 1,6,6, 6-hexachlorocyclohexane
(c) Strecker (d) Wurtz (c)1,6-phenyl-1, 6-chlorohexane
(d) 1, 1-phenyl-6, 6-chlorohexane
7. What is the final product of reaction?

SOCl Product. CH-C= CHNa CH-CH- Product

2 OH
HC6 CHs a ) CH, = C H - C H - C H ,

(b) CH,-CH, -C = C-CH, -CH,

ldentify the product (c) CH C -CH, - CH, - CH

H (d) CH, -C=C- CH, -CH,

8. The following reaction is known as
(a) (b) +HCI
Cl CH, CH,OH +SOC1,ndineC,H,CI+S0,
H.C
HC6 CH CH (a) Kharasch effect
H (b) Darzen's process
(c) Williamson's synthesis
(c) (d) (d) Hunsdiecker synthesis reaction
HSCH, H,c SH 9. What is the main product of the reaction between
-methy
- u

CH HC6 CH propene with HBr?

3. Gem-
dibromide is (a) 1-bromo butane
(a) (6) 1-bromo-2 methyl propane
CH,CH(Br)OH(Br)CH, (b) CH,CBr,CH,
() CH,Br)CH,CH, (c) 2-bromo butane
d) CH,BrCH,Br (d) 2-bromo-2 methyl propane
4.
Ethylidene dibromide is 10. Which one is the strongest nucleophilic sc
in
(a) CH,-CH, - Br (b) Br - CH, - CH, - Br
(c) CH,-CHBr, following species?
(d) CH CBr
=
 10.21
Organic Compounds Containing Halogens
classical
O 15. The reaction shown below goes through
of this reaction?
carbocation. What is the major product

Br

HBr P)

92 (a) trans-1, 3-dibromocyclohexane

(b) 2 (b) cis-1, 3-dibromocyclohexane

(a) (c) trans-1, 2-dibromocyclohexane
(c)3 (d) 4
(d) cis-1, 2-dibromocyclohexane
11. When ethyl alcohol (C,H,OH) reacts with thionyl
16. Decreasing order of reactivity of HX in the reaction
chloride, in the presence of pyridine, the product obtained is
ROH+HX> RX + H,O
(a)CH,CH,CI+HCI (a) HI> HBr> HC1> HF
b) C.H,Cl +HCI +SO,
(b) HBr> HCI > HI >HF
(c)CH,CHCI+ H,O + SO0,
(c) HCl> HBr> HI > HF
(d)CHCH,Cl+HC1+ SO (d)HF> HBr> HCI> HI
12. Preparation of alkyl halides in laboratory is least preferred 17. R-OH +HX> R- X+ H,0
by In the above reaction, the reactivity of different alcohols is
(a) Treatment of alcohols
(a)Tertiary> Secondary> Primary
(b) Addition of hydrogen halides to alkenes
(b) Tertiary < Secondary < Primary
(c)Halide exchange (c)Tertiary< Secondary> Primary
(d) Direct halogenation of alkanes
(d) Secondary < Primary < Tertiary
13. Which of the following organic compounds will give
a mixture of 1-chlorobutane and 2-chlorobutane on 18. In the Hunsdiecker reaction,
chlorination (a) Number of carbon atoms decrease
H b) Number of carbon atoms increase
(c) Number of carbon atoms remain same
(a) C H - C H - C H = CH, (b) H C = C - C = CH, (d) none of the above
19. The catalyst used in Raschig's process is
CH (a) LiAIH, (b) Copper chloride
) CH, =CH-CH = CH, (d) CH, =CH-CH-CH
(c) Sunlight (d) EthanolNa
14. Analyse the following reaction and identify the nature
20. In Finkelstein reaction, which reactants are used
of A and B
(a) Nal +C,H,OH (b) NaF + acetone
BHBr HBr A (c) NaBr+ CH,OH (d)Nal+C,H,Br
Bh
21. (A)C,h (B) -KOH (C) CH,CHO,
Br
Identify A, B and C.

(a) Both Aand B are (a)Ethyl alcohol, Ethyl chloride and Ethane
(b) Ethane, Ethyl chloride and Ethyl alcohol
(6) Both Aand Bare (c) Propane Propyl chloride and Propyl alcohol
Br (d) All of the above
Br
22. Pick up the correct statement about
alkyl halides.
()Ai and Bis (a) They show H-bonding
Br (b) They are soluble in water
Br (c) They are soluble in organic solvent
(d) They do not contain any polar bond
(Ai Br
andBis
 10.22 Chemistry
23. Racemic mixture is obtained due to the halogenation of (b) More no. of alkyl group on the carbon atom
(b) n-pentane (c) Small groups on the carbon attached to tha
(a) isopentane
atom
(c) neopentane (d) Both (a) and (b)
(d) None of these
24. The reaction of SOCl, on alkanols to form alkyl chlorides
32. When ethyl bromide is treated with moist AgO,
gives good yields because
product is/are
(a) alkyl chlorides are immiscible with SOC (a) Ethyl ether (b) Ethanol
(b) the reaction does not occur via intermediate formation (c) Ethoxy ethane (d) All of the above
of an alkyl chlorosulphite
33. The reactivity of ethyl chloride is
(c) alcohol and SOCl, are soluble in water (a) More or less equal to that of benzyl chlonide
(d) the other products of the reaction are gaseous and (b) More than that of benzyl chloride
escape out
(c) More or less equal to that of chlorobenzene
25. How many chiral compounds are possible on (d) Less than that of chlorobenzene
monochlorination of 2-methy! butane?
34. The reactivities of methyl chloride, propyl chloride z
(a)8 (b) 2 chlorobenzene are in the order
(c) 4 (d) 6 (a) Methyl chloride > propyl chloride> chlorobenzu
26. Which branched chain isomer of the hydrocarbon with (b) Propyl chloride> methyl chloride> chlorobenaz
molecular mass 72u gives only one isomer of mono (c) Methyl chloride > chlorobenzene> propyl chlonik
substituted alkyl halide? (d) Chlorobenzene> propyl chloride> methylctione
(a) Tertiary butyl chloride (b) Neopentane 35. Reaction of -butyl bromide with sodium mehout
(c) Isohexane (d) Neohexane produces
27. The reaction conditions leading to the best yield of (a) Isobutane (b) Isobutylene
CHCl are: (c) Sodium -butoxide (d) -butyl methyl eber
(a) C,H (excess) +Cl Vight 36.
CH,-CH,-CI+KCN(aq) -> X+Y
dark
(b) C,H, +C Compounds X and Yare
room temperature
(a) CH,+KCI (b) CH CH,CN+KCI
(c) C.H,+C, (excess) UVlight (e)CH,CH,+ KCI (d) None of these
(d) CH,+C UVlight 37. Ethylidene chloride on treatment with aqueous
28. The chief reaction product of reaction between n-butane gives

and bromine at 130°C is: (a) Ethylene glycol (b) Acetaldehyde

(a) (c) Formaldehyde (d) None
CH,CHCH,CH,Br (b) CH,CH, CHBr
38. CH,Cl+KCN X Hydrolsis Y. Xr and"
CH3 (a) CH, and CH CN
(c) CH-CH Br (d) CH,CH, C Br, (b) C,H,CN and C,H
(c) CH,CN and C,H,CH,NH,
CH,Br CH3 (d) C,H CN and C,H,coOH ofhal
Propertles of Haloalkane and Nucleophillc 39. The set of compounds in which the reactivity
Substitutlon Reactlon atom in the ascending order is
29. The correct order of (a) Vinyl chloride, chloroethane, chlorobenze
dipole moment of alkyl halides is (b) Vinyl chloride, chlorobenzene, chloroetna
(a) RI> RBr < RCI> RF (b) RF> RCI > RBr>RI
() Chloroethane, chlorobenzene, vinyl che
(c) RCI> RF> RBr > RI (d) None of these (d) Chlorobenzene, vinyl chloride chloroetna
30. What would be the
product when neopentyl chloride 40. Vinyl chloride reacts with HCl to form
reacts with sodium ethoxide (a) 1, 1-dichloroethane
(a) 2-Methyl-2-butanol (b) Neo pentyl alcohol (b) 1,2- dichloroethane
(c) Both a and b (d) 2-Methyl-2-butene (c) Tetrachloroethylene
31. reaction is favoured (d) Mixture of 1, 2 and 1, 1-dichloroethane
Syl by:
o v e rnitratc,

41. When ethyl iodide is heated with sile

(a) Non-polar solvent
product obtained is
 Organic Compounds Containing
(a) CHAg (b) Ag-O-NO, Halogens 10.23
(a) Both the reactions take
(e) C,H,O-NO, (d) C.H,I -

NO (6) The first reaction takes

place at the same rate

Fora given alkyl group the densities of the halides follow place faster than second
42. reaction.
the order
b) RI < RCI < RBr (C) The second reaction takes
(a) RI<RBr> RCI place faster than first
reaction.
<RI < RCI (d) RCI< RBr < RI
() RBr (d) Both the reactions take place by
CH 48. Which of the Syl mechanism
following is the example of S2 reaction ?
-D H Product. (a) CH,Br+ OH- CH,OH +Br
3. OH (b) CH,CHCH, +OH-CH,CHCH, + Br
Br OH
Identify the major product:
CH3 (c) CH,CH,OH-20CH,= CH,
CH CH CH
(d) CH- ¢-CH, +OH>CH, - -0-CH,+ Br
Br
CH3 49. Tertiary alkyl halides are practically inert to SN2
mechanism because of.
(d D (a) Insolubility b) Instability
(c) Inductive effect (d) Steric hindrance
44. When alkyl halide is heated with dry Ag,0, it produces 50. The structure ofthe major product formed in the following
(a) Ester (b) Ether reaction:
c) Ketone (d) Alcohol CH,CI
NaCN
5. Alkyl halide can be converted into alkene by is
DMF
(a) Nucleophilic substitution reaction
6) Elimination reaction
(C) Both nucleophilic substitution and elimination CH,CN CH,CI
reaction (a) (b)
d) Rearrangement CN
Ihe increasing order of reactivity of the following CN
someric halides with AgNO, (H,O + alcohol) is: CH,CI CHCN
O H,-CH CH-CH, CH,-Cl
()cH-CH =CH- CH- CH3
= -

(
CI CN
(un)CH C =
CH-CH, CH -
51. A solution of ()-chloro-1-phenylethane in toluene
racemises slowly in the presence of a small amount of
CI SbCl, due to the formation of
(a) carbanion (b) carbene
CHs (c) carbocation (d) free radical
(V)CH C=CH=CH2 52. The order of reactivities of the following alkyl halides for
an Sy2 reaction is:
CI
(a) Il <IV <II<I (a) RF>RCI> RBr> RI (b) FR> RBr> RCI> RI
(b) I<III<IV<I (c) RCI>RBr>RF > RI (d)RI>RBr> RCI> RF
c Il<I<II<IV 53. The following compound on hydrolysis in aqueous
(d) I<which
der the following actions, II <IV< III out at
are carried
the same temperature acetone will give:
CH, CH, CH,
CH-Br+OH C H , - OH +BrQ ..)
CH-0
CH-Br+OH
whiiehch
of the
DMSO CH, -OH+BrQ (i) NO2
actions. following
wing statement is correct about these H CI CH,
 10.24 Chemistry

CH, CH, CH, CH

CH
(K) CH,-0- O NO,
56. CHC-CI NaOHla4) CH-C-OH
CHn)
H HO CH The product obtained will be CHa
(a) d-form (b) -form
CH, CH, CH, (c) racemic mixture mainly (d) none of these
57. Which is the correct reaction coordinatediam
(L)CH- NO following solvolysis reaction?
CH CH
OH H CH HO
NBr OH
CH, CH, CH
(M) CH-0- O AG AG
(a) (b)
H CH, OH
(a) Mixture of (K) and (L) (b) Mixture of (K) and (M) Reaction Coordinate Reaction Coordimae
(c) Only (M) (d) Only (K)
54. The major product of the following reaction is
AG
Me B r
(d) AG

Ph S Na Reaction Coordinate Reaction Coordne

dimethylformamide 58. Rate limiting Sl following the sequence

NO2 R-BrRB-B -
Me SPh SPh (a) (6)
Me
The statement about sequence on the basis of asung
F
that R contains 3 different groups is:
(a) (b) (a) more stable carbocation greater is in the propa
of racemization
ras

NO, (b) the more nucleophilic the solvent the greaie

NO proportion of inversion
Me Br Me SPh
a
C)In above sequence (b) represent separaley s
SPh SPh pair of ions
c) (d) (d) All of these

mpoun

NO, NO, Ellminatlon Reactlon and Polyhalogen CO

55. KI in acetone, undergoes S2 reaction with each of
R and S. The rates of the reaction
P, Q. 59. Ethyl chloride+aq. KOH gives the produe
vary as
(a) CHCH,OH (b)CH-CH

CI
(c) CH=CH (d) CH,CHOK presenr

CI 60.When ethyl alcohol and Ki reacted

P Na,CO. yellow crystals of.. refome
Q R S
(a) P>Q>R>S (a) CHI b) CHI
(b) S> P>R>Q
(c) P>R>Q>S (d) R>P>S>Q ()CH (d) CHI a n db l e n d

61. In preparation of
CHCI, from ethano
powder, the latter provides
 Halogens 10.25
Organic Compounds Containing
NaOH to form
(b) C, 68. Acetone reacts with I, in presence of
(a) CafOH), (b) CH2
(b) (d) None of these (a) CH
Both (a) and (d) CH,I
(c) (c) CHI,
Which
oneof the following compounds undergoes
62. 69. In the given reaction,
reaction most readily?
Br
CH C-CH, X
(a) CH - CH2-CH,
Br
CH
the elimination products
X] as the major product among
b) C H , C H , - C H , - B r
()CH,-CH,-CH,-I iS
CH
CH -CH, (b) C-CH
( (a)
(d) CH C - CH2-CH3 CH
CH,
the following processes does not occur -CH3
63. Which one of
during formation of CHCI, from C,H,OH
and bleaching (C) -CH
powder?

(a) Hydrolysis (b) Oxidation CH for iodoform

(c) Reduction (d) Chlorination 70. Which of the following is responsible
reaction?
64. Chloroform can be obtained from (b) Methanol
(a) Formalin
(a) Methanol (b) Methanal
(c) Acetic acid (d) Ethanol
(c) Propanol-1 (d) Propanol-2 reaction?
71. Which of the following cannot undergo E,
65. Which compound does not form iodoform with alkali and
iodine? (b)
(b) Ethanol (a) Br
(a) Acetone
(c) Diethyl ketone (d) Isopropyl alcohol

66. Which of the following will be most reactive for E,

(d) none of these
(c) Br
reaction?
Br 72. Reaction of ethyl chloride with sodium leads to
(a) Ethane (b) Propane
( C-CH2CH3 (c) n-butane (d) n-pentane
73. 2CHCl +0 2COC1, +2HCI
A Br
In the above reaction, X stands for
(a) An oxidant (b) A reductant
(6) CH-CH- Br (c) Light and air (d) None of these

Br 74. Phosgene is the common name for

(a) CO, and PH (b) Phosphoryl chloride
(c) CH,-CH-CH-CH
Br
(c) Carbonyl chloride (d) Carbon tetrachloride

(d) CH-CH-C-CH,
75. Reaction C,HI+CH,l+ 2Na
CH-CH +2Nal is called

.
CH
Which compound gives yelow ppt. with iodine and
(a) Hoffmann's reaction
(b) Dow's reaction
alkali? (c) Wurtz reaction
(a) 2-hydroxy propane (b) Acetophenone (d) Riemer-Tiemann's reaction
(c) Methyl acetone (d) Acetamide
10.2610.26 Chemistry
80. Which of the following compound
d will mamake
MeO KxX Major most readily with AgN0,?
will
yrecn
(a) CCLCHo (b) CHCI
76. CHCH-C(Br)CH (c) CH CHCI (d) CK
81. CCI, cannot give precipitate with AgNO, de
CH CH Y Major (a) Formation of complex with
Et,COK AgNO,
b) Evolution of Cl, gas
X and Y are respectively:
(c) Chloride ion is not formed
CH ,CH, (CH,),CH H
(a))C-C
CH CHcC
CH
and
CH
c=C(
82.
(d) AgNO, does not give silver ion
E, cB reaction is given by which of the followin
(CH,),CH ,H CH3 ,CH
CCH (a) CF-CHCL, (b) CH,-CH-CR
(6)

CH
CH cCH and

CHs
CH
CH NO
NO,

(C)
CHa
)C-C and c=C (d) All of these

CH CH CH, CHs OcOCH,

(CH) CH ,CH
83. Ethyl bromide reacts with lead-sodium alloy to fom
C C H

and c-c (a) Tetraethyl lead (b) Tetraethyl bromie

CH CH CH (c) Both (a) and (b) (d) None of the above
77. The dehydrobromination of 2-bromobutane gives 84. Iodoform heated with Ag powder to form
CH,CH CHCH. The product is (a) Acetylene (b) Ethylene
(a) Hofmann product (c) Methane (d) Ethane
(b) Saytzeffproduct 85. 1-chlorobutane reacts with alcoholic KOH to fom
(c) Hoffimann-Saytzeff product
a) 1-butene (b) 2-butane
d) Markownikoff product
(c) 1-butanol (d) 2-butanol
78. Which of the following statements about chloroform is
alse? 86. By heating mixture of CHC1, with silver powdz 3
a

(a) It is a colourless, sweet-smelling liquid compound formed is

(b) It is almost insoluble in water (a) Acetylene (b) Silver acetate

(c)It is highly inflammable (c) Methanol (d) None of these

(d) It can be used as an inhalational anaesthetic agent 87. Chloropicrin is
79. In which of the following reaction, regioselectivity can be (a) Trichloro acetaldehyde (b) Nitrochloroform
observed. (c) 2,4,6-trinitro phenol (d) None of these
CH 88. AgNO, does not give precipitate with CHC1,
*
ecaus

(a) CH-C-CH,-CI alc.KOHA (a) CHC1, does not ionise in water

H (b) AgNO, does not reacts with CHCl
CH3 () CHCI, is chemically inert

(b)CH-C-CH alc.KOH/A (d) None of these ethane

89. When (1R, 2R)-1, 2-Dibromo-1, 2-dipheny

CI mo
treated with alcoholic solution of KOH, the
CH3
product would be:
(c) CH-C-CH,-CH, cKOHA, (a) trans-1, 2-diphenyl ethene
CI (b) A mixture of cis, trans alkenyl bromide
CH (c)cis-alkenyl bromide
Veld"
(d) CH-¢-CH,-CI as.KOHA, (d) trans-alkenyl bromide
90. The correct order of S2 / E, ratio for n
CH product of the following halide is
 Organic Compounds Containing Halogens 10.27

Ph (b) These are difficult to synthesise

(c) They deplete ozone layer
( P)
) C H - C H h - C - C H ,

(d) None of these

97. What is the increasing order of reactivity of the following
CH-CH-CH in an E, reaction with ethanolic KOH solution?
CH Br
Ph
I. I.
(R) CH C H , - I

(S)C H - C H - C H - C H ,
Br

II. IV.

(b) R>Q>S>P Br
(a)R> S>Q>P
(a) I<II< III < IV (b) I< II <IV< III
(c)P>R>S>Q (d) Q>P>R>S (c) III<I< II < IV (d) IV< I I < II <I

reaction, alkyl halides react with

91. In Wurtz 98. Freon (dichlorodifluoro methane) is used
Sodium in ether b) Sodium in dry ether
(a) (a) As local anaesthetic
(c) Sodium only (d) Alkyl halide in ether (b) For dissolving impurities in metallurgical process
92. Chloroform reacts
with concentrated HIN0, to give (c) In refrigerator
(a) Water gas (b) Tear gas (d) In printing industry
(c) Laughing gas (d) Producer gas 99. Which of the following is known as freon which is used
of
93. Two percent of ethanol is added during the oxidation
as a refrigerant?

chloroform to stop the formation of carbonyl chloride. In b) CHC1,

(a) CCLF2
this reaction ethanol acts as
(c) CH,F2 (d) CF
(a) Auto catalyst (b) Negative catalyst 100. Which plastic is obtained from CHCIl, as follows
(c) Positive catalyst (d) None of these CHC E X 300CYPolymensationPlastic
94. Provide the structure of the major organic product which SbF3
results in the following reaction. (a) Bakelite (b) Teflon

(c) Polythene (d) Perspex

101. The incorrect statement concerning the given reaction is/
CH,ONa, CH,OH are (X = F, CI, Br, I))

H
CH3 CH
Br C,HONa
H,C CH, CH,OH
X
(a) CH CH
CH CH
H,C I.
CH +HC II.
~CH
(a) (1) is the major elimination product
()
CH CH (b) (II) is formed at faster rate than (I)
(c) (1) is formed at faster rate than (I)
5. In the following reaction X 1s (d) increasing order of reactivity with different X is

CHNH+X+ KOHCH,NC (highly oftensive

odour) F <Cl< Br <I

(b) CHC 102. An isomer of C,H,Cl, on boiling with aqueous KOH

(a) CHC
(d) CCI gives acetone. Hence, the isomer is
(c)CH,CI should not (a) 2, 2-dichloropropane (b) 1, 2-dichloropropane
These compounds
CFCI [Where x + 4].
=
y
be used because
(c) 1, 1-dichloropropane (d) 1, 3-dichloropropane
(a) These are fluorocarbons
 Organic Compounds Containing Halogens 10.29
Cl
(a) Raschig process (b) Wurtz-Fittig reaction
(b) (c) Friedel-Crafts reaction (d) Grignard reaction
125. CH, +
Br Cl2LgN Product. In above reaction
product is
(d) (a) CC CHO
(b)CH,CI,
10. The reagent(s)
for the following conversion. (c) CH,C1, d) CH,C,
is/are CI
Br Br
(a) alcoholic KOH
b) alcoholic KOH followed by NaNH, 126. Diazonium salts+Cu,Cl, +HCI| thereaction
(c) aqueous KOH followed by NaNH is known as
(a) Chlorination (b) Sandmeyer's reaction
d) Zn/CH,OH
121. Select the formula representing the major product of (c)Perkinreaction (d) Carbyl amine reaction
the following reaction 127. m-Bromotoluene is prepared by
Br (a) Bromination of toluene
CH3CH2OK/CH3CH2OH (b) Friedel Craft's reaction of bromobenzene with CH,C
H CH3
(c) Bromination of nitrobenzene and subsequent
CH CH,CH replacement of -NO, group with methyl group
H CH (d) Bromination of aceto-p-toluidine followed by
hydrolysis and deamination
128. Toluene reacts with excess of Cl in presence of sunlight
CH, CHCH, to give a product which on hydrolysis followed by
reaction with NaOH gives
b) -CH3 COONa
H.
H,C
COOH

O bOJ
CHCH,
H CH,CH COONa
()
CH CH
oO Na
(d) None of these

Br 129. Which of the following will best convert nitrobenzene

H
into 3-fluorobromobenzene?
(d) HCO CH Br
NO
CH CH,CH
paratlon of Haloarenes
Properties F/AIC, Zn/HCI, NaNO,/HCI-0°C, CuBr
N= NBF (a)
(b) SnCl/HCI, Br,/FeBr, NaNO,/HBF,-0°C,
heat

(c) SnCL/HCI, NaNO,/HBF,-0°C, heat, Br,/FeBr

A (d) Br,/FeBr, SnCL/HCI, NaNO,/HBF,-0°C,
heat
of FeCl,
130. The reaction of toluene with Cl, in presence
he above process gives *Y'Thus,
a) Fluorobenzene product A is gives X and reaction in presence of light
c) 1,4-difluorobenzene (b) Benzene X and "Y" are:
-chlorotoluene
Y and (d) 1,3-difluorobenzene (a) X Benzyl chloride, Y =
m
alle

Zhave the value of as 1.78, 1.9 and 1.3D

Benzal chloride, Y
-chlorotoluene

a)pectively.
=
o

Which of the following could be X? (b) X =

o-chlorotoluene m-chlorotoluene, Y =
p-chlorotoluene
(c)X
A.e)Chlorp-chlorotoluene
=

(b) m-chlorotoluene Trichloromethyl

and p-chlorotoluene, Y
=

(d) Data insufficient (d) X =

o-

Zene is benzene
prepared commercially by
 10.30 Chemistry
has the 138. Which of the following is Wurtz-Fittig
131. Which one among the
highest dipole moment?
following compounds
(a) C,HI + 2Na ICH,>CH, CH,+Teact
2Na
ion?
(b) C,HI+ Cu +IC > CH-CH+Cul,
(a) o-bromochlorobenzene (b) o-dibromobenzene (c) CHI+2Na above
+ICH3>CH,-CH, 2Na
(c) m-dichlorobenzene (d) o-dichlorobenzene
(d) None of the
be synthesized in the 139. The best yield of given product can be obtained
132. Fluorobenzene (CH F) can
which set of reactants A and B respectively ned by ita
laboratory:
CH
(a) By heating phenol with HF and KF
(b) From aniline by diazotization
diazonium salt with HBF
followed by heating the A+BEther
CH-C-CH,
with
CH
(c) By direct fluorination of benzene F, gas chloride
with NaF solution (a) PhLi +Neopentyl
(d) By reacting bromobenzene (b)-Bu-MgBr+ Benzyl bromide
of FeCl, + Neopentyl bromide
133. The reaction of toluene with Cl, in presence (c) PhMgBr
chloride
(d) Benzylechloride t-Butyl
+
gives predominantly:
(b) Benzyl chloride obtained in the folonn
(a) Benzoyl chloride
140. What is the major product
(c) o- and p-chlorotoluene (d) m-chlorotoluene reaction?
aniline with: C H - Br
134. Chlorobenzene can be prepared by reacting
NH product
(a) hydrochloric acid

(b) cuprous chloride Br

aluminium chloride CH- NH, CH-Br
(c) chlorine in presence of anhydrous
with cuprous (a)
(d) nitrous acid followed by heating NH
Br
chloride.
CH-NH, CH-N
the presence of a
135. The reaction
of biphenyl with HOCI in
strong acid gives (major)
(c NH, (
Cl
NH nucleopu
halides are less reactive towards
-Cl 141. Aryl
substitution reactions as compared to alkyl halides due
carbanion
CI (a) The formation of less stable
C
bond
(b) Longer carbon halogen
-Cl (c) The inductive effect
attached to the halogen
(d)sp-hybridized carbon
of CH,CI, (1, 2, 3, 4, 5,
136. When the all-cis isomer 142. Which will give white ppt. with AgNO,?
the
6-Hexachlorocyclohexane) is heated with alc. KOH,
most probable product is:
CI
Cl
(a) -ci
and (©)
(d) Both (a)
CI ( -CH,CI
(b)
O C1 C 143. What are A and B in the following
reaction:

CI Br
CH,CHO,B
Mg'EtO, A) (ii) aq, NH,C
(c) (d)
MaCl CHOHCH
CI
Chemical Propertles of Haloarenes ( and Br
-Br
137. An aromatic compound of molecular formula CH,Br
CI Cl
was nitrated then three isomers of formula CgH,Br,NO,
were obtained. The original compound is
and
(a) o-dibromobenzene (b) m-dibromobenzene
(d) Both a and c
() MaBr
MgBr -CHOHCH
(c) p-dibromobenzene

1
 Organic Compounds Containing Halogens 10.31

MgCl 150. Following equation illustrates

MgCI
CoHCI+2NaOH UCHONa + NaCl+ H,0
and 200 atm

Br CHOHCH (a) Dow's process (b) Kolbe's process

these
None of (c) Carbylamine test (d) Haloform reaction
(d)
When
lorine is passec through warm benzene in 151. Aryl halide is less reactive than alkyl halide towards
is
of the sunlight, the product obtained
144.
presence nucleophilic substitution because
(a) Benzotrichloride (b) Chlorobenzene
(a) Less stable carbonium ion
(c) G a m m e x a n e
(d) DDT
(b) Due to large C -Cl bond energy
CCl
(c)Inductiveeffect
(d) Resonance stabilization and sp>-hybridisation of C
1eqy. of Br, lFe A. Compounds Ais
attached to halide

CCl CCl 152. Which of the following reaction does not take place?
Br
Br

(a) CH, -OCH, KNH2

Br liq. NH3
CCl CC
C
(b) +aq. KOH
)
Cl
Br Br (c) +alc. KOH
Br
CI
146. Chlorobenzene is
(a) Less reactive than benzyl chloride NaOH +NaOH . 300°C
200 atm
(b) More reactive than ethyl bromide
153. Which of the following procedures would be best for
(c) Nearly as reactive as methyl chloride achieving the following reaction?
d) More reactive than isopropyl chloride
CH 0,N COOH
147. In presence
of AICl, benzene and n-propyl bromide react
in Friedel-Crafts reaction to form C1 CI Br
(a) n-propyl benzene (a) i. NBS in CCl, and heat, ii.
NaNO, ii. KMnO, and
(b) 1,2-dinomal propyl benzene heat

(c)1,4-dinomal propyl benzene (6) i. KMnO, and heat, ii. Br, +FeBr, ii. HNO, and
(d) Isopropyl benzene H,SO
(c) i. NBS in CCl and heat, i. KMnO, and heat, ii.
48. What is product of the
following reaction'? HNO, and H,SO,
(d) i. Br, +
FeBr. i. KMnO, and heat, ii. HNO, and
H,SO
154. Replacement of Cl of chlorobenzene
MeC Cl to give phenol
Br b MgBr requires drastic conditions but
4-dinitrochlorobenzene is readily replaced because
chlorine of 2.

(a) NO, make ring electron rich at ortho and para

(d) None of these
(6) NO, withdraws e from meta position
49.
Chloroben on fusing with solid NaOH gives (c) denotes e at meta position
(a) Benzene (b) Benzoic acid
(d) NO, withdraws e from ortho/para positions
(c) Phenol (d) Benzene chloride
155. What term describes the reactive intermediate formed in
the following reaction?
 10.32 Chemistry
p-bromotoluene, NaNH, NH, -33°C >CH,(CH,) 159. The reaction of chloroform with
with ale
alcoholic
NH, in a ratio 50% para isomer, 50% meta isomer.
p-toluidine forms: KOH
(a) Aryl radical (b) Benzyne formation
(a) H,C- O NHCHCl,
(c) Sigma complex (d) Benzo cation

156. 1,2 di-bromo cyclohexane on dehydrohalogenationgives (b) H,C NC

(a) (b) CN
(c) H,C-
(d) None of these (d) H,CO-N,CI
157. In the conversion of p-nitrofluoro benzene to
160. The compound formed on heating chlorobenzene
p-nitroanisole, intermediate X is involved. chloral in presence of conc. H,SO, is:
The true statements about the intermediate X is/are (a) Hexachloroethane (b) DDT
(I) the intermediate is aromatic. (c) Freon (d) Gammexane
(I1) the intermediate is resonance stabilized anion. 161. Compound (A), CgH,Br gives a yellow precipitate whe
(III) electron withdrawing group on the benzene ring
stabilize the intermediate.
warmed with alcoholic AgNO,. Oxidation of(A)gisg
acid (B), CH,O, (B) easily forms anhydride on
(a) II andII (b) Only 1I heia
Identify the compound (A).
(c) I and III (d) Only I
CH,Br CH
158. Select the correct statement about A and B

Cu, A A
O O Br
NO2 CH3
CH,Br
Me
CHBr
Cu,A B
OL NO2 CH
(a) B is optically active but A does not
CH
104. 1n he reaction of p-chlorotoluene with KNH, Is u
(b) A is optically active but B does not
(c) Both A and B are optically active because of the
NH, the major product is:
presence of chiral centres (a) o-Toluidine (b) m-Toluidine

(d) Both A and B are optically inactive because of the (c)p-Toluidine (d)p-Chloroaniline
presence of vertical plane of symmetry.

SECTION B: STATEMENT RASED OUISTI

 Organic Compounds Containing Halogens 10.33
4 Statement 1:m-butyl chloride has lower b.p. than n-butyl 13. Statement 1: Alkyl iodide can be prepared by treating
bromide
alkyl chloride/bromide with Nal in acetone.
ent 2: The b.p. increases with increase in molar
Statement
Statement 2: NaCINaBr are soluble in acetone while Nal
mass.
isnot.
Statement 1: RI is more reactive than
ment 1: RI RCI towards
N 14. Statement 1: In the E, elimination, B-H and leaving
reaction.

group should be antiperiplanar.

2: The rate of reaction for Sl
tatement

> RCI.
or
S2 Statement 2: In the E, elimination, base always abstracts
is RI
mechanism unhindered -H.
Statement
NBS is a specific reagent for allylic 1S. Statement 1: Bromobenzene upon reaction with Br/te
bromination.
gives 1,4-dibromobenzene as the major product.
Statement 2: Allylic bromination occurs through free Statement 2: In bromobenzene, the inductive effect
of
radical intermediates. the bromo group is more dominant than the mesomeric

7. Statement 1: n-Butyl loride has higher boiling point effecet in directing the incoming electrophile.
than n-butyl bromide. 16. Statement 1: CCI, and H,O are immiscible.
statement 2: C-Clbond is more polar than C- Br bond. Statement 2: CCl, is a polar solvent.
&Statement 1: CH,Br +AgCN>CH,NC+AgBr. 17. Statement 1: Styrene on reaction with HBr gives

Statement 2: CN" is an ambident ion. 1-bromo-1-phenylethane.

9Statement 1: Nucleophilic substitution on an optically
active alkyl halide gives a mixture of enantiomers.
Statement 2: The reaction occurs according to Sy2
mechanism.
10. Statement 1: Butene on reaction with HBr in the presence
peroxide produces 1-bromobutane.
ofa
Statement 2: It involves formation of a primary radical.
11. Statement 1: p-Dichlorobenzene is less soluble in
organic solvents than the corresponding o-isomer.
Statement 2: Benzyl radical is more stable than alkyl
radical.
18. Statement 1: Aryl undergoes nucleophilic substitution
with ease.
Statement 2: The carbon halogen bond in aryl halides
has partial double bond character.
19. Statement 1: Alkyl halides form alkenes when heated
above 300°C.
Statement 2: CH,CH,I react slowly with strong base
when compared to CD,CH,I.

Statement 2: 0-Dichlorobenzene is polar while 20. Statement 1: Nucleophilic substitution reaction on an

p-dichlorobenzene is non-polar. optically active alkyl halide gives a mixture of enantiomers.
Statement 2:The reaction occurs by Syl mechanism.
Statement 1: In ethyl chloride, it
12.
comparison to is 21. Statement 1: Addition of Br to cis-but-2-ene is
difñcult to carry out nucleophilic substitution on vinyl
stereoselective.
chloride
Statement 2: S2 reactions are stereospecific as well as
Statement 2: Vinyl group is electron-donating.
stereoselective.

SECTION C: PREVIOUS YEARS' EXAMINATION QUESTIONS

APMT/NEET Questions 2. What products are formed when the following

is treated with Br, in the presence of FeBr,?
compound
In the 2014
following sequence of reactions CH
4Br KCNAH;0BiAlH4_C
Ether
the end
product is |2012 CH
a) acetaldehyde (b) ethyl alcohol CH, CH,
(c) acetone (d) methane Br
(a and
cH CH
Br
10.34 Chemistry
7. The major product formed in the
the following teacian
followina
CH CH CH
Br CH-C-CH2-BrCHO
and CHOH
(b)
CH CH3 CH3
CH CH3
Br (a) CH-C-CH,OCH,
(c) and

CH CH3 (b) CH-CH-CH2 -CH,

Br OCH
CH CH CH3
and (c) CH-C=CH2
(d) CH CH3
CH Br
Br (d) CH-C-CH,
there is: [2015 Re]
3. In an Sl reaction on chiral centers,
(a) 100% retention OCH
(b) 100% inversion 8. Themajor product obtained on treatment ofCHCHCHA
(c) 100% racemization CH, with CH,O/CH,OH is [2011
(a) CH,CHCH(OCH,)CH, (6) CH,CH = CHCH,
(d) inversion more than retention leading to partial
racemization
(c) CH,CH,CH = CH,
(d) CHCHCH,CH,OCH,
be used for the
4. Which of the following reaction(s) 9. Which of the following is liquid at room temperature?
can

preparation of alkyl halides?

[2015 Re] (b) CH,Br 2013
(a) CHI
anh. Znl2 (d) CHF
(1) CH,CH,OH + HCI (c)C.H,CI af
(1I) CH,CH,OH +HCI 10. Which one of the following is the comrect formula
dichlorodiphenyl trichloroethane? 12013
(11)(CH,),cOH+HC1-
HC H CI
IV) (CH,),CHOH + HCIanh.
ZnClh_
(a) (IV) only (b) (III) and (IV) only
aO--a O - -
(c) T), II and (IV) only (d) () and () only

5. The compound C,H undergoes the following reactions:

CI
CH >A BRZaHC H
The product 'C' is
(a) m-bromotoluene
2018
(b) o-bromotoluene
(c) 3-bromo-2,4,6-trichlorotoluene
(d) p-bromotoluene
11. Which of the followingis used in fire extinguishers (2014

AlIMS Questlons (a) CH (b) CHCl

(c) CH,C1, (d) CCl, (201

6. 12. Which of the following is an anaesthetic?

Among the following, the one which reacts most
with ethanol is readily (a) CH b) CHC
(a) p-nitrobenzyl bromide [2011] (c) CH,CI (d) C,H,OH a r d sa l c o h o l

13. Among the following the most reactivetowa 05

(b) p-chlorobenzyl bromide
KOH is
(c) p-methoxybenzyl bromide (a) CH, = CHBr (b) CH,COCH,CH,Br

(d) p-methylbenzyl bromide (d) CH,CH,CH,Br

(c) CH,CH,Br
 Organic Compounds Containing Halogens 10.35
following reactions will yield (c)
Which
of the (d) CI
14. 2, 2-dibromopropane?
[2016]
(a) HC=CH +2HBr

(b)CH, -C =CH +2HBr Assertlon-Reasoning Questlons

(c) CH,-CH
=
CH, +HBr
Br +
HBr These questions consist of two statements each, printed as
(d) CH,-CH = CH- Assertion and Reason. While answering these questions you
reaction is faster in [2016
15. SI are required to choose any one of the following four responses:
CH
(a) CH,CH,CI CHCH-CI
(a) If both the assertion and reason are true and reason is a

true explanation of the assertion.

CH
(b) If both the assertion and reason are true but the reason is
(d) CH-CH-Cl
(c) CHC-CI not the correct explanation of assertion.

If the assertion is true but is false.

CH CH, (c) reason

(d) If assertion is false but reason is true.

CH,
Nal in acetone and
19. Assertion: CHI, gives a precipitate with AgN0, solution
16. (R)-2-lodobutane is treated with on heating but CHCl, not.
allowed to stand for a long time. The product eventually
formed is [2017 Reason: C - I bond is quite weak as compared to C -
CI
bond. [2011]
(a) (R)-2-iodobutane b) (S)-2-iodobutane
(d) ( - 1 , 2-diiodobutane 20. Assertion: The reactivity order for SI reaction is Ar,CX
c) #H2-iodobutane
17. Decreasing order of reactivity in Williamson synthesis of >Ar,CHX>ArCH,X.
the following: [2017 Reason: More is the stability of carbocation, more readily
) Me CCH,Br (I) CH,CH,CH,Br it is formed. [2013
(III) CH, = CHCH,CI TV) CH,CH,CH,CI 21. Assertion: Trans-2-chloro propene has higher dipole
(a)II > II> IV>I (b) I>II >IV> III moment than cis-2-chloro propene.
(c) II> I1 >IV>I (d)I> II>II>IV Reason: The resultant vector sum of all the vectors
18. [2018] in trans-2-chloro propene is more than cis-2-chloro
propene. 2014]
HCL
22. Assertion: lodine is more soluble in CCI, than in water.
Reason: Non-polar solutes are more soluble in non-polar
(a) Cl (a) solvents. 2016
23. Assertion: Chlorination of allylic hydrogen is difficult
than vinylic hydrogen.
Reason: Allyl radical is stabilised by resonance.
2016
 Organic Compounds Containing Halogens
10.37
2. NaOH: 3.)
NaOH; 3. NaNO, H,SO,: 4. ethanol 29. When phenyl magnesium bromide reacts with tert-
HC 2.
c)
1Fe.
HC: 2 NaOH; 3. NaNO,. H,SO,;4. H,O, heat butanol, the product would be
1.F,
(dh
ntaining C,HI
conta.
CH,CH,I lost their original
and (a) Benzene (b) Phenol
elled
A and B for testing. A and B
labelle
There
were
(c) tert-butylbenzene (d) tert-butyl phenyl ether
els. taken in test tube and boiled with NaOH
Br
uere
separately

solution in each tube was made acidic NH2

ution.
end s
The
then some AgNO, solution was O NaNH
dilute HNO, and liq NH,
B gave a yellow precipitate. Which one
Substance
The reaction is
ed. statement is frue for the experiment:
pollowing
ofthefo
(a)B
was CH (a)Arsy
Addition fHNO, was unnecessary b) Ars2
(b)
CH,I (c) Nucleophilic substitution via benzyne formation
(o)A
was

CH,CH,I
d)A
was (d) none of these

ANSWERS KEY
SECTIONA
(a) 3. (b) 4. 5. (a) 6. d)
2. (a) 7. (d) 3. (b) 9. d) 10.

12. 6) 13. (d) 14. (c) 15. (a) 16. (a) 17. (a 20. (d)
18. (a) 19. (6)
22. (c) 23. (d) 24. (d) 25. (b) 26. (b) 27. (a) 28. (b) 29. (c) 30. (d)
1. (6)
32. (d) 33. (b) 34. (a) 35. (b) 36. (b) 37. (b) 38. (d) 39. (d) 40. (a)
J1. ()
42. (d) 43. (a) 44. (b) 45. (b)46. (c) 47. (o) 48. (a) 49. (d) 50. (d)
. (c)
52. (d) 53. (a) 54. (a) 55. (b) 56. (c) 57. (b) 58. (d) 59. (a) 60. (a)
S1. (c)
62. (d) 63. (c) 64. d) 65. (c) 66. (a) 67. (b) 68. (c) 69. (c)70. (d)
. (0)
TL) 72 ) 73. (c) 74. () 75. (c) 76. (a) 77. b) 78. (c) 79. (c) 80. (d)
82. (d) 83. (a) 84. (a) 85. (a) 86. (a) 87. b) 88. (a) 89. (d) 90. (a)
() 92. (b) 93. (b) 94. (b) 95. (b) 96. 97. b) 98. (c) 99. (a) 100. (b)
I0L. ) 102. (a) 03. b) 104. (a) 105. (b) 106. (a) 107. (c) 108. (6) 109. (c) 110. (c)
L ( 112. (6) 113. (c) 114. (b) 115. (d) 116. (a) 117. (b) 118. (d) 119. (d) 120. (b)
11. ) 122. (a) 123. (b) 124. (a) 125 6) 126. (b) 127. (d) 128. (6) 129. (d) 130. (d)
LBL() 132. (b) 133. c) 134. (d) 135. (b) 136. (b) 137. (b) 138. (a) 139. (b) 140. (a)
ML ( 142. (d) 143. (b) 144. () 145. (a) 146. (a) 147. (d) 148. (c) 149. (c) 150. (a)
151 152. (a) 153. (d) 154. (d) 155. (b) 156. (a) 157. (a) 158. (a) 159. (b) 160. (b)
161. () 162. (b)
SECTION B
L ( 2. (d) 3. (a) 4. (a) 5. (a) 6 (b) 7. (d) 8. b) 9. (c) 10. ()

)12. () 13. b) 14. (c) 15. (c) 16. (c) 17. (c) 18. (d) 19. (c) 20. (a)

ECTION C
() 2 (c) 3. (d) 4. (c) 5. (a) 6. c) 7. (d) 8. (b) .
(a 10. (a)
L12. 13. (d) 14. (b) 15. (c) 16. (b) 17. (c) 18. ) 19. (a) 20. (a)
) 22. (a) 23. (d)
TON D
2. (a) 3. (b) 5. (c) 6. (a) 7. (b) 8. (c) 9. (a) 10. (b)
(012.
22. 6)
a) 13. (a)
4.

14. (c)
(b)
15. (a) 16. (c) 17. (a) 18. (d) 19. (d) 20. ()

23. () 24. (a) 25. (a) 26. (b) 27. (d) 28. (c) 29. (a) 30. (c)