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Class 12 - Chemistry
Term 1 - Haloalkanes and Haloarenes - 01

1. Ethyl benzene cannot be prepared by ______.

a. Clemmensen reduction
b. Wurtz – Fittig reaction
c. Friedel – Crafts reaction
d. Wurtz reaction

2.

In the reaction, 2 – Bromopentane on heating with alcoholic KOH, forms two compounds: Pent – 1 – ene
and Pent – 2 – ene. Which one of the following statements is true?
a. Pent – 1 – ene is formed as a major product
b. Both in equal proportion
c. Pent – 2 – ene is formed as a major product
d. Sometimes Pent –1 – ene is the major product and other times Pent – 2 – ene
3. Benzylic halides contains:
a. sp3-hybridized carbon atom, next to an aromatic ring bonded to a halogen.
b. sp2-hybridized carbon atom next to an aromatic ring.
c. sp3-hybridized carbon atom next to carbon-carbon double bond.
d. a halogen atom bonded to an alkyl group.
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4. In the given reaction,

2 – Bromopentane on heating with alcoholic KOH, forms two compounds: Pent – 1 – ene and Pent – 2 –
ene. If one major and one minor product are formed, then:
a. there is formation of more than one alkenes due to the availability of more than one - hydrogen
atoms.
b. the minor product formed is Pent-1-ene which has the lesser number of alkyl groups attached to
the C=C.
c. the major product formed is Pent-2-ene which has the greater number of alkyl groups attached to
the C=C.
d. All of these
5. The iodine-containing hormone produced by our body is:
a. Progesterone
b. Insulin

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c. Thyroxine
d. Adrenaline
6. Arrange the following compounds in the increasing order of their densities.

a.

b.

c.

d.

a. (d) < (c) < (b) < (a)

b. (a) < (b) < (c) < (d)
c. (a) < (c) < (d) < (b)
d. (b) < (d) < (c) < (a)
7. C - Cl bond in chlorobenzene in comparison to C - Cl bond in methyl chloride is:
a. longer and stronger
b. shorter and weaker
c. longer and weaker
d. shorter and stronger
8. A halogen used in potential blood substitutes in surgery is:
a. Fluorine
b. Bromine
c. Iodine
d. Chlorine
9. The following
i. (CH3)2CHCH2CH2Cl
ii. (CH3)2CHCH(Cl)CH3

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iii. (CH3)2C(Cl)CH2CH3
iv. CH3CHCH2(Cl)CH2CH3

are the possible structural isomers expected to be formed if one of the hydrogen atoms is replaced by
chlorination. The original compound is
a. CH3(CH2)2CH2CH3
b. (CH3)2CHCH2CH3
c. (CH3)3CHCH2CH2CH3
d. (CH3)2CHCH3
10. The reaction RX + 2Na + RX R – R + 2NaX is called ________.
a. Fittig reaction
b. Williamson’s synthesis
c. Sandmeyer’reaction
d. Wurtz reaction

For question numbers 11-15, two statements are given- one labeled Assertion (A) and the other labeled
Reason (R). Select the correct answer to these questions from the codes (a), (b), (c) and (d) as given
below:
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a. Both A and R are true and R is the correct explanation of A.

b. Both A and R are true but R is not the correct explanation of A.
c. A is true but R is false.
d. A is false but R is true.

11. Assertion (A): Vinyl chloride is less reactive than alkyl chloride.
Reason (R): Stability of alkyl halide decreases as the strength of C-X bond decreases.
12. Assertion (A): Carbon-halogen bond in aryl halide has a partial double bond character.
Reason (R): Aryl halides undergo nucleophilic substitution easily.
13. Assertion (A): Aryl iodides can be prepared by reaction of arenes with iodine in the presence of an
oxidising agent.
Reason (R): Oxidising agent oxidises I2 into HI.
14. Assertion (A): Boiling point of alkyl halides increases with an increase in molecular weight.
Reason (R): Boiling point of alkyl halides is in the order RI > RB > RCl > RF.
15. Assertion (A): p-Dichlorobenzene has higher melting point than o-dichlorobenzene.
Reason (R): Stronger the van der Waals' forces of attraction, the higher is the melting point.

Question No. 16 to 20 are based on the given text. Read the text carefully and answer the questions:

A primary alkyl halide (A) C4H9Br reacted with alcoholic KOH to give compound (B). Compound (B) is
reacted with HBr to give compound (C) which is an isomer of (A). When (A) reacted with sodium metal, it
gave a compound (D) C8H18 that is different than the compound obtained when n-butyl bromide reacted
with sodium metal.

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16. IUPAC name of compound (D) is

a. 2,5-dimethylhexane
b. 3,4-dimethylhexane
c. 2-methylheptane
d. n-octane
17. When compoound (C) is treated with alc. KOH and then treated with HBr in presence of peroxide, the
compound obtained is
a.

b.

c. CH3CH2CH2CH2Br

d.
18. Compound (A) is
a. CH3CH2CH2Br

b.

c.

d. CH3CH2CH2CH2Br
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19. Which type of isomerism is present in compound (A) and (C)?
a. Chain
b. Positional
c. Functional
d. Both positional and functional
20. Identify compound (B).
a.

b. None of these
c. CH3-CH=CH-CH3
d. CH3-CH2-CH=CH2

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Class 12 - Chemistry
Term 1 - Haloalkanes and Haloarenes - 01

Solution

Section A
1. (d) Wurtz reaction
Explanation: Alkyl halides react with sodium in dry ether to give hydrocarbons containing double the
number of carbon atoms present in the halide. This reaction is known as the Wurtz reaction.
2RX + 2Na R-R + 2NaX
So, C6H5CH2CH3 is not prepared by the Wurtz reaction.
2. (c) Pent – 2 – ene is formed as a major product
Explanation: Pent-2-ene is the major product as substituted alkene is formed in major quantity
according to Zaitsev (Saytzeff's) rule. The process is known as β− elimination as it involves the
elimination of β− Hydrogen.
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3. (a) sp3-hybridized carbon atom, next to an aromatic ring bonded to a halogen.
Explanation: Benzylic halides are the compounds in which the halogen atom is bonded to an sp3-
hybridized carbon atom next to an aromatic ring. For example C6H5CH2Cl.
4. (d) All of these
Explanation: Zaitsev (also pronounced as Saytzeff) formulated a rule: In dehydrohalogenation
reactions, the preferred product is that alkene which has the greater number of alkyl groups attached
to the double-bonded carbon atoms. So the major alkene will be the more substituted alkene i.e. Pent-2-
ene.
5. (c) Thyroxine
Explanation: Our body produces iodine-containing hormone, thyroxine, the deficiency of which
causes a disease called a goiter.
6. (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.
7. (d) shorter and stronger
Explanation: In chlorobenzene, the hybridization of carbon attached to Cl is sp2, and in methyl
chloride hybridization of C attached to Cl is sp3. In sp2 hybridization, s-character is 33% and in sp3 s-
character is 25%. The sp2 hybridized carbon with a greater s-character is more electronegative and can
hold the electron pair of C—X bond more tightly than sp3-hybridized carbon in haloalkane with less s-
character resulting in a short bond length of C-Cl bond. Since it is difficult to break a shorter bond than
a longer bond, means it is stronger. Also in chlorobenzene, the electron pairs on Cl atom are in
conjugation with π-electrons of the ring, so C—Cl bond acquires a partial double bond character due to
resonance which makes the bond stronger.
8. (a) Fluorine
Explanation: Certain fully fluorinated compounds are being considered as potential blood substitutes

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in surgery. So fluorine is the element used in these blood substitutes.

9. (b) (CH3)2CHCH2CH3
Explanation:

this is the original compound.

10. (d) Wurtz reaction
Explanation: The given name reaction is the Wurtz reaction. When 2 moles alkyl halide reacts with
sodium then it is called Wurtz reaction.
11. (b) Both A and R are true but R is not the correct explanation of A.
Explanation: Vinyl chloride itself shows resonance structure and thus stabilized.
As vinyl chloride has partial double bond character thus breaking of C-Cl bond is difficult which makes
vinyl chloride less reactive than alkyl chloride.

12. (c) A is true but R is false.

Explanation: Aryl halides undergo nucleophilic substitution with difficulty.
13. (c) A is true but R is false.
Explanation: Oxidising agents like HIO3 oxidise HI to I2 because, in their absence, the presence of HI
makes the aryl iodides go back to being arenes.
14. (b) Both A and R are true but R is not the correct explanation of A.
Explanation: The greater the molecular mass, the stronger the van der Waals' forces of attraction and
hence higher is the melting point/boiling point.
15. (b) Both A and R are true but R is not the correct explanation of A.
Explanation: Among dichlorobenzenes, the p-isomer being symmetrical, packs closely in the crystal
lattice and hence has much higher melting point than o- and m-isomers.
16. (a) 2,5-dimethylhexane

Explanation:

17. (d)

Explanation:

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18. (c)

Explanation: When compound (A) reacted with Na-metal, it gave a compound D(C8H18) which is
different from the compound obtained when n-butyl bromide reacted with Na metal and hence the
compound (A) must be isobutyl bromide.

2CH3CH2CH2CH2Br + 2Na CH3CH2CH2CH2CH2CH2CH2CH3

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19. (d) Both positional and functional

Explanation:

20. (a)

Explanation:

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