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Halo Alkanes and Halo Arenes
Halo Alkanes and Halo Arenes
benzene
Q1
(v)
1Chloromethyl3(2, 2dimethylpropyl)
1Bromo2(1methylpropyl) benzene
Answer
(vi)
(i)
1Bromo3, 3dimethyl1phenylbutane
(vii)
1chloro1(4iodophenyl)3,3dimethylbut1ene
(ii)
1Bromo2ethyl2methylbutane
Q2
4Bromo4methylpent2ene
MUKESH SHARMA
DPS JODHPUR
Q4
(ii)
1Bromo2methylpropane
Answer
Q3
Name the following compounds according to IUPAC
system.
(i)
(i)
(ii)
(ii)
Q5
(iii)
(i)
(iv)
(v)
(ii)
(vi)
(iii)
MUKESH SHARMA
DPS JODHPUR
(iv)
(v)
(v)
Answer1
(vi)
(vii)
Answer
(i)
(i) 2, 2, 4-Trimethylpentan-3-ol
(ii) 5-Ethylheptane-2, 4-diol
(iii) 1-Methoxy-2-methylpropane
(iv) 2, 6-Dimethylphenol
(v) 2-Ethoxybutane
(vi) 1-Phenoxyheptane
(vii) Ethoxybenzene
Q1
(ii)
(iii)
(iv)
(i)
(ii)
(v)
(iii)
(iv)
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DPS JODHPUR
(vi)
(vi)
Q2
Answer2
Answer 3
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Q4
(ii)
(iii)
Answer 5
(iv)
Answer 4
(i)
1bromo1methylcyclohexane
In the given compound, all -hydrogen atoms are equivalent.
Thus, dehydrohalogenation of this compound gives only one
alkene.
(i)
(ii)
(ii)
(iii) In the given compound, there are two different sets of
equivalent -hydrogen atoms labelled as a and b. Thus,
dehydrohalogenation of the compound yields two alkenes.
(iii)
(iv)
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DPS JODHPUR
2,2,3-Trimethyl-3-bromopentane
In the given compound, there are two
different sets of equivalent hydrogen atoms labelled as a and b.
Thus, dehydrohalogenation of the compound yields two
alkenes.
(i)
(ii)
(iii)
(iv)
(v)
(vi)
(vii)
(viii)
(ix)
(x)
(i)
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DPS JODHPUR
Ethanol to but-1-yne
Ethane to bromoethene
Propene to 1-nitropropane
Toluene to benzyl alcohol
Propene to propyne
Ethanol to ethyl fluoride
Bromomethane to propanone
But-1-ene to but-2-ene
1-Chlorobutane to n-octane
Benzene to biphenyl.
(v)
(ii)
(vi)
(iii)
(vii)
(iv)
(viii)
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DPS JODHPUR
(x)
(ii)
(iii)
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(iv)
(v)
(ix)
(vi)
(x)
(xi)
(vii)
(xii)
(viii)
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DPS JODHPUR
(xvi)
(xiii)
(xiv)
(xvii)
(xviii)
(xv)
(xix)
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(xx)
Q3
Answer
(i) If propene is allowed to react with water in the presence of an acid
as a catalyst, then propan-2-ol is obtained.
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Finkelstein
reaction.
2 Swarts Reaction Preparation of alkyl fluoride by reaction of
metallic fluoride such as AgF, Hg2 F2, CoF2, or SbF3 with alkyl
halides
3 Friedel-Crafts reactions
[1]FriedelCrafts Alkylation
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5 Wurtz-Fittig reaction:-
[ii]Friedel-Crafts Acylation
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Q2
Q1
Answer
hydrocarbon with the molecular formula, C5H10
belongs to the group with a general molecular formula C nH2n.
Therefore, it may either be an alkene or a cycloalkane.
Since hydrocarbon does not react with chlorine in the dark, it cannot
be an alkene. Thus, it should be a cycloalkane.
Further, the hydrocarbon gives a single monochloro compound,
C5H9Cl by reacting with chlorine in bright sunlight. Since a single
monochloro compound is formed, the hydrocarbon must contain
Hatoms that are all equivalent. Also, as all Hatoms of a cycloalkane
are equivalent, the hydrocarbon must be a cycloalkane. Hence, the
said compound is cyclopentane.
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A
p-Dichlorobenzene is more symmetrical than o-and misomers. For this reason, it fits more closely than o-and m-isomers in
the crystal lattice. Therefore, more energy is required to break the
crystal lattice of p-dichlorobenzene. As a result, p-dichlorobenzene
has a higher melting point and lower solubility than o-and m-isomers.
Q2 Why C-Cl bond is more polar than C-F bomnd
A2
Q3
Explain why
(i) the dipole moment of chlorobenzene is lower than that
of cyclohexyl chloride?
Q1
p-Dichlorobenzene has higher m.p. and lower solubility
than those of o- and m-isomers. Discuss.
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(i)
(ii)
Therefore, Grignard reagents should be prepared under anhydrous
conditions.
Q4 Out of C6H5CH2Cl and C6H5CHClC6H5, which is more easily
hydrolysed by aqueous KOH?
A4
Hydrolysis by aqueous KOH proceeds through the formation of
carbocation. If carbocation is stable, then the compound is easily
hydrolyzed by aqueous KOH. Now,
while
(iii)
A5
(i)
2-bromobutane is a 2
alkylhalide whereas 1-bromobutane is a 1 alkyl halide. The
approaching of nucleophile is more hindered in 2-bromobutane than in
1-bromobutane. Therefore, 1-bromobutane reacts more rapidly than
2-bromobutane by an SN2 mechanism.
forms 1-carbocation,
is hydrolyzed more
(ii)
by aqueous KOH.
Q5
Which alkyl halide from the following pairs would you
expect to react more rapidly by an SN2 mechanism? Explain your
answer.
(iii)
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DPS JODHPUR
Q6
In the following pairs of halogen compounds, which
compound undergoes faster SN1 reaction?
(i)
Q8
Which compound in each of the following pairs will react
faster in SN2 reaction with OH?
(ii)
A6
A8
(i) In the SN2 mechanism, the reactivity of halides for the same
alkyl group increases in the order. This happens because as the size
increases, the halide ion becomes a better leaving group.
RF << RCl < RBr < RI
Therefore, CH3I will react faster than CH3Br in SN2 reactions with OH.
(i)
(ii)
The alkyl halide (I) is 2 while (II) is 1. 2 carbocation is more stable
than 1 carbocation. Therefore, (I), 2chloroheptane, undergoes
faster SN1 reaction than (II), 1-chlorohexane.
Q9
Arrange the compounds of each set in order of reactivity
towards SN2 displacement:
Q7
Haloalkanes react with KCN to form alkyl cyanides as
main product while AgCN forms isocyanides as the chief
product. Explain.
A7
KCN is predominantly ionic and provides cyanide ions in
solution. Although both carbon and nitrogen atoms are in a position to
donate electron pairs, the attack takes place mainly through carbon
atom and
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A 9 (i)
(iii)
(ii)
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A12
Q11
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O
n the other hand, an alcoholic solution encourage removal of a
hydrogen from the -carbon of the alkyl chloride and form an alkene
by eliminating a molecule of HCl.
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(a) CH CH CH OH
ans b), CO bond is more stable in
resonance.
3
ans i) Compound A :
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(b) because of
:
DPS JODHPUR
Compound B
(ii) Compound B.
9. Write the structures and names of the compounds formed when
compound A with molecular formula, C H is treated with Cl in the
presence of FeCl .
ans.
7
11. Which of the following compounds will have the highest melting
point and why?
; 1-Bromo-2,2-dimethylpropane
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DPS JODHPUR
15. Which of the following haloalkanes reacts with aqueous KOH most
easily? Explain giving reason.
(i)
1-Bromobutane(ii) 2-Bromobutane(iii) 2-Bromo-2methylpropane
(iv) 2-Chlorobutane
ans (iii); The tertiary carbocation formed in the reaction is
stable.
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DPS JODHPUR
1.
2.
3.
4.