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2nd PUC Chemistry Question Bank Chapter

10 Haloalkanes and Haloarenes
December 9, 2019

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Karnataka 2nd PUC Chemistry Question Bank

Chapter 10 Haloalkanes and Haloarenes

2nd PUC Chemistry Haloalkanes and Haloarenes NCERT Textbook

Questions

Question 1.
Name, the following halides according to IUPAC system and classify 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)2CH3I
(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-CICH2C6H4CH2C(CH3)3
(xii) o-Br-C6H4CH(CH3)CH2CH3
Answer:

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Question 2.
Give the IUPAC names of the following compounds:
(i) CH3CH(CI)CH(Br)CHCH3
(ii) CHF2CBrClF
(iii) ClCH2C = CCH2Br
(iv) (CCl3)3CCl
(v) CHCH3C(p-ClCCH6HCH4)CH2CH(Br)CHCH3
(vi) (CH3)3CCH=ClCC6`H4I-p
Answer:
Question 3.
Write the structures of the following organic halogen compounds.
(i) 2-Chloro-3-methylpentane
(ii) p-Bromochlorobenzene
(iii) l-Chloro-4-ethylcyclohexane
(iv) 2-(2-Chlorophenyl)-l-iodooctane
(v) Perfluorobenzene
(vi) 4-tert-Butyl-3-iodoheptane
(vii) l-Bromo-4-sec-butyl-2-methyl- benzene .
(viii) l,4-Dibromobut-2-ene
Answer:
Question 4.
Which one of the following has the highest dipole moment?
(i) CH2Cl2
(ii) CHCl3
(iii) CCl4
Answer:
CCl4 is a symmetrical molecule. Therefore, the dipole moments of all four C-Cl bonds
cancel each other. Hence its resultant dipole moment is zero.

As shown in the above figure, in CHCl3, the resultant dipole moments of two C-Cl
bonds is opposed by the resultant dipole moments of one C-H and one C-Cl bond.
Since the resultant of one C-H and one C-Cl bond is smaller than the resultant of the
two C-Cl bonds dipole moments, the opposition is to a small extent. As a result
CHCl3 has a small net dipole moment.

On the other hand, in case of CH2,Cl2 the resultant of the dipole moments of two C-Cl
!"#$%&'
bonds !" resultant
()*$%&'by the
is strengthened # $of the dipole moments of two C-H bonds. As a
!"#$"%"&"
% CH2&Cl2 has
result, ' a higher
( )dipole moment. Hence CH2Cl2 has the highest dipole
'()%*++&,
moments among the three compounds.
Hence, the given compounds can be arranged in the increasing order of their dipole
moments as
CCl4 < CHCl3 < CH2Cl2

Question 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:
A hydrocarbon with molecular formula, C5H10 belongs to the group with a general
molecular form CnH2n. therefore, it may either be an alkene or a cycloalkane since
hydrocarbon does not react with chlorine in the dark, it cannot be alkene. Further, the
hydrocarbon gives a single monochloro compound, C5H9Cl by reacting with chlorine in
might sunshine since the formed compound is monochloro one all the C-H bonds
should be equivalent. Hence the compound should be a cycloalkane. Hence the
compound is C5H10 (cyclopentane).

Question 6.
Write the isomers of the compound having formula C4H9Br.
Answer:
There are four isomers of the compound having the formula C4H9Br. These isomers
are given by

Question 7.
Write the equations for the preparation of 1-iodobutane from
(i) 1-butanol
(ii) 1-chlorobutane
(iii) but-l-ene.
Answer:
Question 8.
What are ambident nucleophiles? Explain with an example.
Answer:
Ambident nucleophiles are nucleophiles having two nucleophilic sites. Thus ambident
nucleophiles have two sites through which they can attack. For example, nitrite ion is
an ambident nucleophile.

Nitrite ion can attack through oxygen resulting in the formation of alkyl nitrites. Also, it
can attack through nitrogen resulting in the formation of nitroalkanes.

Question 9.
Which compound in each of the following pairs will react faster in SN2 reaction with
OH?
1. CH3Br or CH3I
2. (CH3)3CCl or CH3Cl
Answer:
1. In the SN2 mechanism the reactivity of halides for the same alkyl group increase in
the order. This happens because as the size increases the halide ion becomes a better
leaving group.
R-F << R-Cl < R – Br < R-I
Therefore, CH3I will react faster than CH3Br in SN2 reaction with image 17.

2. The SN2 mechanism involves the attack of the nucleophile at the atom bearing the
leaving group. But, in case (CH3)3 CCl, the attack of the nucleophile at the carbon
atom is hindered by the presence of the bulky substituents on that carbon atom
bearing-the leaving group in CH3Cl. Hence CH3Cl reacts faster than (CH3)3 CCl in SN2
reaction with

Question 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:
1. 1-Bromo-l-methylcyclohexane
2. 2-Chloro-2-methylbutane ,
3. 2,2,3-Trimethyl-3-bromopentane.
Answer:
1.

In this compound, all β hydrogens are equivalent thus dehydrohalogenation gives only
one alkene.
2.

In the given compound, there are two different sets of equivalent P – hydrogen atoms
labelled as ‘a’ and ‘b’ thus dehydrohalogenation yields two alkenes.

Sayt zeff’s rule implies that in dehydrohalogenate reactions, the alkene having a
greater number of alkyl groups attached to a doubly bonded carbon atoms is
preferably produced.
Therefore, 2-methyl but – 2- ene is the major product in the reaction.

3.

In the given compound, there are two different sets of equivalent P – hydrogen atoms
labelled as ‘a’ and ‘b Thus dehydrogenation of the compound yields two alkenes.
2 -1 thyl – 3, 3 – demethyl but – tene
Again according to Saytzeff’s rule
3,4,4 – trimethylpent – 2- ene is the major product.

Question 11.
How will you bring about the following conversions?
(i) Ethanol to but-l-yne
(ii) Ethane to bromoethene
(iii) Propene to 1-nitropropane
(iv) Toluene to benzyl alcohol
(v) Propene to propyne
(vi) Ethanol to ethyl fluoride
(vii) Bromomethane to propanone
(viii) But-l-ene to but-2-ene
(ix) 1-ChIorobutane to n-octane
(x) Benzene to biphenyl.
Answer:
Question 12.
Explain why
1. The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride?
2. Alkyl halides, though polar, are immiscible with water?
3. Grignard reagents should be prepared under anhydrous conditions?
Answer:
1.

In chlorobenzene, the Cl-atom is linked to a sp2 hybridized carbon atom. In cyclohexyl

chloride, the Cl atom is linked to a sp3 hybridized carbon. Now, sp2 hybridized carbon
has more s-character than sp3 hybridized carbon atom. Therefore, the former is more
electronegative than the latter. Therefore, the density of electrons of C-Cl bond near
the Cl-atom is less in chlorobenzene than in cyclohexyl chloride. Moreover, the-R
effect of the benzene ring of chlorobenzene decreases the electron density of the C-
Cl bond near the Cl-atom. As a result, the polarity of C-Cl bond in chlorobenzene
decreases. Hence, the dipole moment of chlorobenzene is lower than that of
cyclohexyl chloride.

2. To be miscible with water, the solute-water force of attraction must be stronger than
the solute solute and water-water forces of attraction. Alkyl halides are polar
molecules and so held together by dipole-dipole interactions. Similarly, strong H-
bonds exist between the water molecules. The new force of attraction between the
alkyl halides and water molecules is weaker than the alkyl-halide- alkyl halide and
water-water forces of attraction. Hence, alkyl halides (though polar) are immiscible
with water.

3. Grignard reagents are very reaction. In the presence of moisture, they react to give
alkanes
R-Mg-X + H 2O → RH + Mg(OH)X
Therefore, Grignard reagents should be prepared in anhydrous conditions.

Question 13.
Give the uses of freon 12, DDT, carbon tetrachloride and iodoform.
Answer:
Uses of freon – 12:
Freon -12 (dichlorodifluoromethane, CF2Cl2) is commonly known as CFC. It is used as
a refrigerant in refrigerators and air conditioners. It is also used in aerosol spray
propellants such as body sprays, hair sprays etc. However, it damages the ozone layer.
Hence its manufacture is banned.

Uses of DDT:
DDT (p, p – dichlorodiphenylchloroethane) is one of the best known pesticides. It is
very effective against mosquito and lice. However, due to its harmful effects, its
manufacture is banned;
Uses of carbon tetrachlorides (CCl4):

It is used for manufacturing refrigerants and propellants for aerosol cans.

It is used as feedstock in the synthesis of CFCs and other chemicals.
It is used as a solvent in the manufacture of pharmaceutical products.
CCl4 was once widely used as a cleaning fluid, a degreasing agent in industries, a
spot remover homes, and a fire extinguisher.

Uses of iodoform (CHI3):

Iodoform was used as an antiseptic, but now it has been replaced by other
formulations containing iodine-due to its objectionable smell. The antiseptic property
of CHI3 is only due to the liberation of free iodine when it comes in contact with the
skin.

Question 14.
Write the structure of the major organic product in each of the following reactions:

Answer:
Question 15.
Write the mechanism of the following reaction:

Answer:
The given reaction is

The reaction is an SN2 reaction. In this reaction, CN– acts as the nucleophile and
attacks the carbon atom to which Br is attacked. CN– is an ambident nucleophile and
can attack through both C and N. In this case, it attacks through the C-atom.

Question 16.
Arrange the compounds of each set in order of reactivity towards SN2 displacement:
1. 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane
2. l-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 3-Bromo-2-methylbutane
3. 1-Bromobutane, l-Bromo-2, 2-dimethylpropane, l-Bromo-2-methylbutane, l-Bromo-
3-methylbutane.
Answer:
1.

An SN2 reaction involves the approaching of the nucleophile to the carbon atom to
which the leaving group is attached. When the nucleophile is sterically hindered, then
the reactivity towards SN2 displacement decreases. Due to the presence of
substituents, hindrance tp the approaching nucleophile increases in the following
order.
1- Bromopentane < 2-bromopentane < 2 – Bromo-2-methyl butane
Hence, the increasing order of reactivity towards SN2 displacement is
2- Bromo – 2- methyl butane < 2-bromopentane < 1-Bromopentane

2.

since steric hindrance in alkyl halides increases in the order of 1° <2° < 3°, the
increasing order of reactivity towards SN2 displacement is 3° < 2° <1°.
Hence, the given set of compounds can be arranged in the increasing order of their
reactivity towards
SN2 displacement as:
2-Bromo – 2- methyl butane < 3-bromo-2-methylbutane < 1-Bromo -3- methy
lbutane.

3.

The steric hindrance to the nucleophile in the SN2 mechanism increases with a
decrease in the distance of the substituents form the atom containing the leaving
group. Further, the steric hindrance increases in the increases with increase in the
number of substituents. Therefore, the increasing order of steric hindrances in the
given compounds is as below:
1- Bromobutane < l-Bromo-3-methylbutane < 1 -Bromo-2-methylbutane < 1 -Bromo-
2, 2- demethylbutane.
Hence, the increasing order of reactivity of the given compound towards SN2
mechanism is
l-Bromo-2, 2-dimethylbutane < 1 -Bromo-2-methyl butane < l-Bromo-3-methylbutane
< 1-Bromobutane.

Question 17.
Out of C6H5CH2Cl and C6H5CHClC6H5, which is more easily hydrolysed by aqueous
KOH?
Answer:
Question 18.
p-Dichlorobenzene has higher m.p. and solubility than those of o- and m-isomers.
Discuss.
Answer:

p-Dichlorobenzene is more symmetrical than o- and m- isomers. For this season, 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 higher mp and lower solubility than o- and m- isomers.

Question 19.
How the following conversions can be carried out?
(i) Propene to propan-l-ol
(ii) Ethanol to but-l-yne
(iii) 1-Bromopropane to 2-bromopropane
(iv) Toluene to benzyl alcohol
(v) Benzene to 4-bromonitrobenzene
(vi) Benzyl alcohol to 2-phenylethanoic acid
(vii) Ethanol to propanenitrile
(viii) Aniline to chlorobenzene
(ix) 2-ChIorobutane to 3, 4-dimethyIhexane
(x) 2-Methyl-l-propene to 2-chloro-2-methylpropane
(xi) Ethyl chloride to propanoic acid
(xii) But-l-ene to n-butyliodide
(xiii) 2-ChIoropropane to 1-propanol
(xiv) Isopropyl alcohol to iodoform
(xv) Chlorobenzene to p-nitrophenol
(xvi) 2-Bromopropane to 1-bromopropane
(xvii) Chloroethane to butane
(xviii) Benzene to diphenyl
(xix) tert-Butyl bromide to isobutyl bromide
(xx) Aniline to phenylisocyanide
Answer:
Question 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:
In an aqueous solution, KOH almost completely ionises to give OH– ions. OH– ions is a
strong nucleophile, which leads the alkyl chloride to undergo a substitution reaction to
form alcohol.

On the other hand, an alcoholic soln of KOH contains alkoxide (RO–) ion, which is a
strong base. Thus, it can abstract a hydrogen from the β – carbon of the alkyl chloride
and form an alkene by eliminating a molecule of HCl.

OH– ion is a much weaker base than RO– ion. Also, OH– ion is highly solvated in an
aqueous solution and as a result the basic character of OH’ ion decreases. Therefore,
it cannot abstract a hydrogen from β – carbon.

Question 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:
There are two primary alkyl halides having the formula C4H9Br. They one n-butyl
bromide and isobutyl bromide

Since (a) reacts with Na to give a compound C8H18 which is different from the
compound formed
when n – butyl bromide is reacted with Na, (a) has to be isobutyl bromide.

Question 22.
What happens when
(i) n-butyl chloride is treated with alcoholic KOH,
(ii) bromobenzene is treated with Mg in the presence of dry ether,
(iii) chlorobenzene is subjected to hydrolysis,
(iv) ethyl chloride is treated with aqueous KOH,
(v) methyl bromide is treated with sodium in the presence of dry ether,
(vi) methyl chloride is treated with KCN?
Answer: