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Chapter-10
Haloalkanes & Haloarenes
Class-XII
Subject-Chemistry
10.1 Name the following halides according to IUPAC system and classify them as
alkyl, allyl, benzyl (primary, secondary, tertiary), vinyl or aryl halides:
i.
(CH3)2CHCH(Cl)CH3
ii.
CH3CH2CH(CH3)CH(C2H5)Cl
iii. CH3CH2C(CH3)2CH2I
iv.
(CH3)3CCH2CH(Br)C6H5
v.
CH3CH(CH3)CH(Br)CH3
vi.
CH3C(C2H5)2CH2Br
vii.
CH3C(Cl)(C2H5)CH2CH3
viii. CH3CH=C(Cl)CH2CH(CH3)2
ix.
CH3CH=CHC(Br)(CH3)2
x.
p-ClC6H4CH2CH(CH3)2
xi.
m-ClCH2C6H4CH2C(CH3)3
xii.
o-Br-C6H4CH(CH3)CH2CH3
Answer 10.1
i.
l e a rcnb s e.i n
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iii.
l e a rcnb s e.i n
vii.
viii.
x.
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1Chloro4(2methylpropyl) benzene (Aryl halide)
xi.
xii.
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Answer 10.2
i.
2Bromo3chlorobutane
ii.
1Bromo1chloro1, 2, 2trifluoroethane
iii.
1Bromo4chlorobut2yne
iv.
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2 (Trichloromethyl) 1,1,1,2,3,3,3heptachloropropane
v.
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Answer 10.3
i.
2-Chloro-3-methylpentane
ii.
p-Bromochlorobenzene
iii.
1-Chloro-4-ethylcyclohexane
iv.
2-(2-Chlorophenyl)-1-iodooctane
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v.
Perfluorobenzene
vi.
4-Tert-Butyl-3-iodoheptane
vii.
1-Bromo-4-sec-butyl-2-methylbenzene
viii.
1,4-Dibromobut-2-ene
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10.4 Which one of the following has the highest dipole moment?
i.
CH2Cl2
ii.
CHCl3
iii. CCl4
Answer 10.4
CH2Cl2
= 1.60D
CHCl3
CCl4
= 1.08D
=0D
10.5 A hydrocarbon C5H10 does not react with chlorine in dark but gives a single
monochloro compound C5H9Cl in bright sunlight. Identify the hydrocarbon.
Answer 10.5
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C5H10 may either be an alkene or a cycloalkane. Also, we know that hydrocarbon does
not react with chlorine in the dark, it cannot be an alkene. Thus, it should be a
cycloalkane.
The reactions involved in the question are:
Cyclopentane (C5H10)
Answer 10.6
There are four isomers of the compound C4H9Br.
CH
CH
CH
CH
1Bromobutane
Br
2Bromobutane
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1Bromo2methylpropane
2Bromo2methylpropane
Answer 10.7
i.
CH
CH
CH
CH
ZnC l
2
OH HI
CH
1 -b u ta n o l
ii.
CH
CH
CH
CH
CH CH
CH
CH
CH
CH
CH
CH
CH
I H 2O
1 -io d o b u ta n e
CH
d r y a c e to n e
C l N a I C H
p e r o x id e
H B r
CH
CH
CH
CH
CH
CH
CH
I N aC l
N a I /d r y a c e to n e
B r
iii.
2
CH
I N aBr
Answer 10.8
Ambident nucleophiles: These are nucleophiles which have two nucleophilic sites through which they can
attack.
l e a r cnb s e.i n
When it attacks through oxygen, it forms alkyl nitrites and when it attacks through
nitrogen, it forms nitroalkanes.
10.9Which compound in each of the following pairs will react faster in SN2 reaction
with OH?
i.
CH3Br or CH3I
ii.
(CH3)3CCl or CH3Cl
Answer 10.9
i.
In the SN2 mechanism, the reactivity of halides for the same alkyl group
increases in the following order.
RF << RCl < RBr < RI
As size increases, the halide ion becomes a better leaving group. Thus, CH3I
will react faster than CH3Br in SN2 reactions with OH.
ii.
10.10 Predict all the alkenes that would be formed by dehydrohalogenation of the
following halides with sodium ethoxide in ethanol and identify the major
alkene:
i.
1-Bromo-1-methylcyclohexane
ii.
2-Chloro-2-methylbutane
iii. 2,2,3-Trimethyl-3-bromopentane.
Answer 10.10
i.
1bromo1methylcyclohexane
In this compound, all -hydrogen atoms are equivalent. Thus,
dehydrohalogenation of this compound gives only one alkene.
ii.
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In this compound, there are two different -hydrogen atoms. Thus,
dehydrohalogenation of the compound yields two alkenes.
2,2,3-Trimethyl-3-bromopentane
In the given compound, there are two equivalent -hydrogen atoms. Thus,
dehydrohalogenation of the compound yields two alkenes.
l e a cr b
n s.ei n
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Answer 10.11
i.
SO C l
2
C H 3C H 2O H
C H 3C H 2C l S O 2 H C l
p y r id in e
E th a n o l
C h lo r o e th a n e
H C C H N aN H
L iq u id N H
3
HC CNa
E th y n e
S o d iu m a c e ty lid e
C H 3C H 2 C l H C C N a C H 3C H 2 C C H N a C l
C h lo r o e th a n e
B u t-1 -y n e
ii.
C H 3C H
B r / U V ra ys
2o r
C H 3C H 2 B r H B r
heat
E th a n e
B r o m o e th a n e
C H 3 C H 2 B r
CH
A lc . K O H
B r o m o e th a n e
B rC H
CH
2 4
B rC H
E th e n e
C H 2 B r
CH
V ic -D ib r o m id e
CH 2Br
V ic -D ib r o m id e
A lc . K O H
Br /CCl
CHBr
B ro m o e t h a n e
iii.
C H 3C H C H
P
2H B r C H
P
AgN O
2
C H3 C H B 2r
CH
2
1 -B ro m o p ro p a n e
CH
C H N3 O A g B2r
1 -N itro p ro p a n e
iv.
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v.
vi.
CH 3 CH
PCl
AgF
O H 5
C H 3C H 2 C l
C H 3C H 2 F
E th a n o l
c h lo r o e th a n e
E th y l flo u rid e
vii.
K C N a lc
M gBr
3
CH 3 Br
C H 3 C N 3 C H 3 C C H 3 N M g B r
C H 3C O C H 3
CH
H O
viii.
C H 3C H 2 C H C H
B u t-1 -e n e
C H 3C H 2 C H
HBr
Br CH 3
2 -B ro m o b u ta n e
C H 3C H C H C H 3
lc K O H
B u t -2 -e n e
ix.
2 C H 3 C H 2C H 2 C H
1 -c h lo r d r u c ta n e
D ry e th e r
Cl 2Na
C H 3C H 2 C H 2C H 2C H 2C H 2C H 2C H
n -O c ta n e
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10.12 Explain why
i.
The dipole moment of chlorobenzene is lower than that of cyclohexyl
chloride?
ii.
Alkyl halides, though polar, are immiscible with water?
iii. Grignard reagents should be prepared under anhydrous conditions?
Answer 10.12
i.
iii.
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10.13 Give the uses of freon 12, DDT, carbon tetrachloride and iodoform.
Answer 10.13
Uses of Freon 12:
Uses of DDT:
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10.14 Write the structure of the major organic product in each of the following
reactions:
a c e to n e
C H 3 C H 2 C H 2 C l N aI
i.
heat
ii.
C H 3 3 C
Br KOH
h ea t
eth a n o l
B r C H 2C H 3
N aO H
w a ter
iii.
C H 3C H
iv.
C H 3 C H 2 B r K C N
v.
vi.
vii.
viii.
a q . e th a n o l
C 6 H 5O N a C 2 H 5C l
C H 3C H 2 C H 2 O H S O C l2
C H 3C H 2C H C H
p e r o x id e
H B r
C H 3C H C C H 3 H B r
2
Answer 10.14
i.
CH 3 CH
2C H
C l 2 N a I
C H
heat
a c e to n e
1 -c h lo ro p ro p a n e
CH
3 C H
I 2 N a C l
1 -Io d o p ro p a n e
ii.
iii.
C H 3C H
B r C H 2C H 3
N aO H
C H 3C H O H C H 2 C H 3 N a B r
w a te r
2 -b ro m o b u ta n e
b u ta n e -2 -o l
a q . e th a n o l
iv.
C H 3 C H 2 B r K C N C H 3 C H 2 C N K B r
b ro m o b u ta n e
v.
C 6 H 5O N a C 2 H 5C l C 6 H
c y a n o e th a n e
O C 2H
N aC l
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vi.
C H 3 C H 2 C H 2 O H S O C l 2 C H 3C H 2 C H 2 C l S O 2 H C l
1 -p ro p a n o l
vii.
C H 3 C H 2C H C H
1 -c h lo ro p ro p a n e
H B r
C H 3 C H 2C H 2 C H 2 B r
P e r o x id e
B u t-1 -e n e
1 -B r o m o b u ta n e
viii.
2
5
nBuBr + K CN
2 n B u C N
Answer 10.15
The given reaction is:
C H OH H O
2
5
nBuBr K C N
2 n B u C N
K CN
C H 3C H 2 C H 2 C H 2 B r C H 3C H 2 C H 2 C H 2 C N K B r
n -B u ty l b ro m id e
n -B u ty l c y a n id e
10.16 Arrange the compounds of each set in order of reactivity towards SN2
displacement:
i.
2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane
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ii.
iii.
Answer 10.16
i.
We know that, steric hindrance in alkyl halides increases in the order of 1 <
2 < 3.
Thus, compounds can be arranged in the increasing order of their reactivity as:
2-Bromo-2-methylbutane < 2-Bromo-3-methylbutane < 1-Bromo-3methylbutane
l e a r cnb s e.i n
C6H
CH
Cl C6H
B e n z y l c h lo r id e
C6H
CH
Cl
CH
1 -c a r b o c a tio n
C6H
C h lo r o d ip h e n y lm e th a n e
C6H
CH C6H
2 c a r b o c a tio n
0
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reactions, we can observe that benzyl chloride forms 1-carbocation,
while chlorodiphenylmethane forms 2-carbocation.
This is known that, 20 carbocation is more stable than 1-carbocation. Hence,
chlorodiphenylmethane is hydrolyzed more easily than benzyl chloride by
aqueous KOH.
10.18 p-Dichlorobenzene has higher m.p. and lower solubility than those of o- and
m-isomers. Discuss.
Answer 10.18
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l
xi.
xii.
xiii.
xiv.
xv.
xvi.
xvii.
xviii.
xix.
xx.
Answer 10.19
i.
CH 3 CH CH
P
2
CH
H B r / P e r o x id e
C H3 C H
1 -B ro m o p ro p a n e
K O qH
2 B r
C H
2
CH
CH
P ro p a n e -1 -o l
ii.
OH
3
iii.
C
1
C2 H
B
C
A
K l
Oc
H.
B
o
r
p
/
3
nP
er
C
o
p2
e-
C
r
nB
er
iv.
v.
vi.
vii.
r
CH 3 CH
p e
Bd
2O H 2
CH
C H3 B r A
C H
2 e th aqn o l
KCN
CH
C N3
viii.
ix.
x.
xi.
CH
CH
C l a
C H
q . e th a n o l
KCN
E th y lc h lo rid e
CH
/H O
C N K C l 2
CH
P ro p a n e n itrile
CH
COOH
P ro p a n o ic a c id
xii.
CH 3 CH
B u t-1 -e n e
xiii.
CH CH
CH
e r o x id e
HBr
CH
CH
1 -B ro m o b u ta n e
CH
B r D
C H
ry a c e to n e
N aI
CH
CH
n -B u ty lio d id e
CH
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CH
CH
Cl CH 3
KOH
a lc
CH
2 -C h lo r o p r o p a n e
CH
CH
CH
CH CH
HCl
CH
p e r o x id e
HBr
P ro p e n e
2
Br KOH
aq
CH
CH
CH
CH
Br
1 -B r o m o p r o p a n e
CH
OH
1 -P r o p a n o l
xiv.
CH 3 CH
O H CH 3
C rO
O
3
CH 3 CO CH
x id a tio n
Is o p ro p y l a lc o h o l
CH
N aO I
P ro p a n o n e
COONa CHI3
I o d o fo rm
xv.
xvi.
CH
CH
Br
CH
KOH
2 -B ro m o p ro p a n e
a lc
CH
CH CH
HBr
CH
p e r o x id e
HBr
P ro p e n e
CH
CH
1 -B ro m o p ro p a n e
xvii.
CH
CH
2 N a / D ry e th e r
Cl
CH
C h lo r o e th a n e
CH
CH
CH
2 N aC l
B u ta n e
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Br
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xviii.
xix.
xx.
10.20 The treatment of alkyl chlorides with aqueous KOH leads to the formation of
alcohols but in the presence of alcoholic KOH, alkenes are major products.
Explain.
Answer 10.20
In an aqueous solution, KOH ionizes & produces to give OH ions. OH ion is a
strong nucleophile, which undergo a substitution reaction & forms alcohol.
R C l K O H aq R O H K C l
In the alcoholic solution of KOH, it contains alkoxide (RO) ion, which is a strong
base than OH ion. Thus, it abstracts one hydrogen atom from the -carbon of the
alkyl chloride and forms an alkene & eliminates a molecule of HCl.
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l e a rcnb s .ei n
R CH 2 CH 2 Cl KOH
a lc
R CH CH
K C l H 2O
10.21 Primary alkyl halide C4H9Br (a) reacted with alcoholic KOH to give
compound (b).Compound (b) is reacted with HBr to give (c) which is an isomer
of (a). When (a) is reacted with sodium metal it gives compound (d),
C8H18 which is different from the compound formed when n-butyl bromide is
reacted with sodium. Give the structural formula of (a) and write the equations
for all the reactions.
Answer 10.21
C4H9Br exists in two structures: -
Now,
Compound (a) reacts with Na metal to give compound (b) of molecular
formula, C8H18, which is different from the compound formed when nbutyl
bromide reacts with Na metal. Thus, compound (a) must be isobutyl bromide.
l e a rc nb s .ei n
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Also, compound (b) reacts with HBr to give compound (c) which is an isomer
of (a). Thus, compound (c) is 2bromo2methylpropane.
Answer 10.22
i.
n -b u ty l c h lo rid e
ii.
C l a
C H 3 C H 2C H C H
lc . K O H
K C l H 2O
B u t-1 -e n e
l e a rcnb s .ei n
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iii.
iv.
aq
C H 3 C H 2 C l C H 3 C H 2 O H K C l
v.
When methyl bromide is treated with sodium in the presence of dry ether,
ethane is formed. This reaction is known as the Wurtz reaction.
d r y e th e r
2C H 3B r 2 N a
C H 3C H
vi.
2 N aBr
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