Solution

Class 12 - Chemistry

Haloalkane & Haloarene

1. (d) Electrophilic substitution reaction
Explanation: This is example of electrophilic aromatic substitution (EAS) reaction.Single Cl ion replaces
hydrogen atom and here FeCl3 acts as halogen carriers.

2. (a) Fluorine
Explanation: Certain fully fluorinated compounds are being considered as potential blood substitutes in
surgery. So fluorine is the element used in these blood substitutes.
3. (b) CH3CH2CH2CH2Cl
Explanation: The forces of attraction between the molecules of a compound get stronger as they get bigger
in size and have more electrons. Also, for a straight-chain compound, the points of interaction between the
molecules are more than for a branched compound having the same molecular formula. Thus
CH3CH2CH2CH2Cl has the highest melting point since it is the longest chain compound among the given
options.
4. (b) Chloramphenicol
Explanation: Chlorine containing antibiotics, chloramphenicol, produced by soil microorganisms is very
effective for the treatment of typhoid fever. Chloramphenicol is an antityphoid drug.
5. (d) 3-Bromopentane
Explanation: From the common name of the given compound, we can deduce there are two –C2H5 groups,
one –Br group bound to a CH4 molecule. Bromomethane would appear as CH3—Br. For
diethylbromomethane, two ethyl groups can be substituted for the hydrogens in the methyl molecule,
forming (C2H5)CH(C2H5)Br. To provide an IUPAC name, we need to identify the longest parent chain. CH3—
CH2—CH(Br)—CH2—CH3 is identified as the parent chain, and the –Br group from either side is attached to
the third carbon atom (3-bromo). The number of carbons in the parent chain are five ( which called pent),
so the compound is called 3-bromopentane.
6. (c) 2-Bromobutane
Explanation:

2-Bromobutane

It is a chiral molecule since it does not contain plane symmetry and centre of symmetry.
7. (b) (a) < (b) < (c) < (d)
Explanation: Alkyl halides are heavier in density than water. Their densities are based on the masses of
the halogen atoms and the number of halogen atoms, and also the carbon atoms. Simply putting, the
atomic mass of Br is 79u and that of Cl is 35u. From the molecules, (d) will have the heaviest mass as it
contains 2 Br, followed by (c), (b), and (a). Density is directly proportional to mass, hence the order will be
the same in terms of reducing densities.

8. (a) Mixture of and

Explanation:

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 The reaction of aromatic arenes with chlorine in the presence of Lewis acid catalysts like iron (III) chloride
gives ortho and para isomers of haloarenes by an electrophilic substitution reaction. Cl2 forms a

coordination complex with FeCl3, forming Cl+FeCl4- complex, which gives a slight positive charge to Cl, and

FeCl4- is negatively charged. This Cl+ then reacts with the aromatic double bonds of the toluene molecule to
form an addition product, followed by deprotonation to form a mixture of o- p- and m- isomers of the
chlorotoluene. The m- isomer is very unstable, so the product form is o-Halotoluene and p-Halotoluene.
9. (a) 1,2-dichloroethane
Explanation: Dihaloalkanes having the same halogen are classified as geminal halides or gem-dihalides
and vicinal halides or vic-dihalides. Gem-dihalides are molecules where halogen atoms are present on the
same carbon atom where Vic-dihalides are those dihaloalkanes where the halogen atoms are present on
two adjacent carbon atoms. In common naming system, the gem-dihalides are named as alkylidene
halides, vic-dihalides are named as alkylene dihalides. Dichloromethane contains only one carbon, so
adjacent halogen atoms cannot occur in the molecule. 1,2-dichloroethane contains two carbon atoms with
adjacent halogen atoms. Ethylidene chloride, as its common name states, is a gem-dihalide. Allyl chloride
contains only one chlorine atom.
10. (b) 1-Bromo-2-methylbutane
Explanation: First, we need to identify the longest carbon chain. Once we do that, the actual structure
should read CH3—CH2—CH(CH3)—CH2—Br. –Br, the functional halide group is attached to the first carbon
atom (1- Bromo), so we start the numbering from that position. The methyl group branch is bond to the
second carbon atom in the chain(2-methyl). The number of carbons in the unbranched parent chain is
four, thus giving the name butane. The IUPAC is named 1-Bromo-2-methylbutane.
11. (d) 1, 4 – dibromobutane
Explanation:
Of all the given options, it is possible with 1,4-dibromobutane to form cyclobutane as shown
by intramolecular wurtz reaction.

12. (a) All of these

Explanation: Since halogen atoms are more electronegative than carbon, the carbon-halogen bond of alkyl
halide is polarized; the carbon atom bears a partial positive charge whereas the halogen atom bears a
partial negative charge.

13. (b) a halogen atom bonded to an sp2-hybridized carbon atom of a carbon-carbon double bond.
Explanation: Vinylic halides are the compounds in which the halogen atom is bonded to an sp2-hybridized
carbon atom of a carbon-carbon double bond (C = C). For example CH2=CHBr.

14. (d) b, c
Explanation: Chiral molecules(the object which is non-superimposable on their mirror image) contains
one carbon atom surrounded by four non-identical species. All straight-chain molecules cannot be chiral
because of the presence of two or more identical groups like hydrogens. Even the carbons with double or
triple bonds to a group cannot be considered as a chiral carbon. An asymmetric carbon needs to be
surrounded by four species different from each other through covalent bonds. Hence, the atoms b and c
are asymmetric.

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15. (d)

Explanation: The compound is an enantiomer of compound (A) because the configuration of two groups,
i.e. CH3 and C2H5 in them is reversed at the chiral carbon.

16. (a) the force of attraction between the alkyl halide and water is weaker and cannot overcome the force of
attraction between alkyl halide and alkyl halide as also that of water and water molecules
Explanation: In alkyl halides, there exist dipole-dipole attractions whereas in water van der Waal's forces
or the hydrogen bonding exists. It is difficult for alkyl halides to break these hydrogen bonds, hence
making them almost insoluble in water.
17. (d) A is false but R is true.
Explanation: Haloalkanes react with AgCN to form alkyl isocyanides as the main product while KCN forms
alkyl cyanides as the chief product.
18. (a) Both A and R are true and R is the correct explanation of A.
Explanation: In chlorobenzene, due to resonance partial double bond character appears in the bond
between C & Cl atom and we all know that replacing partial double bond character is a bit difficult than
replacing the single bond as present in the C-Cl bond in chloroethane.
19. (a) Both A and R are true and R is the correct explanation of A.
Explanation: Nitro Group present on ortho and para position of haloarenes act as an electron-
withdrawing group and thus there is the deficiency of electrons makes it more reactive towards
nucleophilic substitution reaction.
20. (d) A is false but R is true.
Explanation: The —NO2 group is a meta-directing group by m-nitro chlorobenzene is not a stable
compound, and the products of the reactions contain nitro groups at o- and p- positions.
21. State True or False:
a) (b) False
Explanation: False
b) (a) True
Explanation: True
c) (b) False
Explanation: False
d) (a) True
Explanation: True
e) (b) False
Explanation: False
22. Fill in the blanks:
a) 1. sp2
b) 1. Iodoform
c) 1. Anhydrous
d) 1. Aryl halides
e) 1. AgNO3

23.

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24.

25. The chemical name of Iodoform is Triiodomethane. It has an antiseptic property because of its property of
release of free iodine but not due to iodoform itself.
26. The IUPAC name of CH3CH2C(CH3)2CH2I is 1-Iodo-2, 2-dimethylbutane.
It is a 1° alkyl halide as the halogen is attached to a primary C.
1 2 3 4 5

27. C H3 − C H − C H2 − C H − C H 3
| |
Br Cl

2−bromo−4−choloropen tan e

Numbering will be done in alphabetically manner

28. In allylic halides, the halogen is bonded to the sp3-hybridised carbon atom next to a carbon-carbon double
bond. Thus,

is an allylic halide.

29.

3-(4-chlorophenyl)-2-methylpropane

30.

3-bromo-2-methylprop-1-ene
F Cl

| |

31. F−
2
C H− C − F
1

Br

IUPAC Name: 1-Bromo-1-chloro-1, 2, 2-trifluoroethane

32. The IUPAC name of CH3C(C2H5)2CH2Br is 1-Bromo-2 ethyl -2- methylbutane.
It is a 1° alkyl halide as the halogen is attached to a primary C.
33. In writing the IUPAC name, we first count the number of C atoms in the longest C chain (parent chain) and
assign the locants according to the functional groups attached. Here as we can see the longest chain contains
4 C and it is an alkane, so we name it butane. The -Br (bromo) group is attached at position 1 and 3. So the
name of the compound is 1,3-dibromobutane.
4 3 2 1

34. C H3 − C = C − C H2 OH
| |

CH3 Br

2 - bromo - 3 - methyl - but - 2 - en - 1 - ol

35. 2, 3–dibromo-1-chloro-3-methylpentane
36. 1-Chloro-1-phenylethane
37. Hydrocarbon which gives only one monochlorination product is
CH3

H3 C − C − C H3
|

CH3

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 CH3

3 |

38. C H3 − 2
C − C H2 Br
|

CH3

1-bromo-2,2-dimethyl propane

39.

4-tert-butyl-3-iodoheptane
40. Ethyl chloride undergoes hydrolysis to form ethyl alcohol (through SN2 nucleophilic substitution).
C2 H5 C l+ K OH(aq) → C2 H5 OH + K C l
Ethylchloride Ethanol

41. The IUPAC name is (CH3)2CHCH(Cl)CH3 is 2-Chloro-3-methylbutane.

It is a 2° alkyl halide as the halogen is attached to a secondary C.

42.

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