Chemistry

HALOALKANES AND HALOARENES

Class 12 - Chemistry

1. Read the text carefully and answer the questions: [5]

Haloarenes are less reactive than haloalkanes. The low reactivity of haloarenes can be attributed to
- resonance effect

sp2 hybridisation of C-X bond

- polarity of C-X bond
- instability of phenyl cation (formed by self-ionisation of haloarene)
- repulsion between the electron rich attacking nucleophiles and electron rich arenes.
Reactivity of haloarenes can be increased or decreased by the presence of certain groups at certain positions for

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example, nitro (-NO2) group at o/p positions increases the reactivity of haloarenes towards nucleophilc
substitution reactions.
(i)
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Aryl halides are less reactive towards nudeophilic substitution reaction as compared to alkyl halides due to

a) larger carbon-halogen bond b) resonance stabilisation

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c) the formation of less stable carbonium d) inductive effect.
ion
(ii) The reactivity of the compounds
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i. MeBr,
ii. PhCH2Br,
iii. MeCl,
u

iv. p-MeOC6H4Br
Ga

decreases as:

a) (iv) > (iii) > (i) > (ii) b) (i) > (ii) > (iii) > (iv)

c) (iv) > (ii) > (i) > (iii) d) (ii) > (i) > (iii) > (iv)
(iii) Which of the following aryl halides is the most reactive towards nucleophilic substitution?

a) b)

c) d)

(iv) Which chloro derivative of benzene among the followings would undergo hydrolysis most readily with
aqueous sodium hydroxide to furnish the corresponding hydroxy derivative?

a) b)

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 c) C6H5Cl d)

(v) Which one of the following will react fastest with aqueous NaOH?

a) b)

c) d)

2. Read the text carefully and answer the questions: [5]

A primary alkyl halide (A) C4H9Br reacted with alcoholic KOH to give compound (B). Compound (B) is

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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.
(i) IUPAC name of compound (D) is
ata
kh
a) 2,5-dimethylhexane b) 3,4-dimethylhexane

c) 2-methylheptane d) n-octane
(ii) When compoound (C) is treated with alc. KOH and then treated with HBr in presence of peroxide, the
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compound obtained is

a) C H3 C H2 C H2 C H − Br b) CH

|
3

|
CH C H3 − C − Br
u

3
|
CH
3
Ga

c) CH3CH2CH2CH2Br d)
CH
3

C H3 − C H − C H2 − Br

(iii) Compound (A) is

a) CH3CH2CH2Br b) CH

|
3

C H3 − C − Br
|
CH
3

c) C H3 C H − C H2 Br d) CH3CH2CH2CH2Br
|
CH
3

(iv) Which type of isomerism is present in compound (A) and (C)?

a) Chain b) Positional

c) Functional d) Both positional and functional

(v) Identify compound (B).

a) C H3 − C = C H2 b) None of these
|
CH
3

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 c) CH3-CH=CH-CH3 d) CH3-CH2-CH=CH2

3. The best method for the conversion of an alcohol into an alkyl chloride is by treating the alcohol with: [1]

a) SOCl2 in presence of pyridine b) PCl3

c) Dry HCl in the presence of anhydrous d) PCl5

ZnCl2

4. Molecules whose mirror image is non-superimposable over them are known as chiral. Which of the following [1]
molecules is chiral in nature?

a) 2-Bromopropan-2-ol b) 2-Bromopropane

c) 2-Bromobutane d) 1-Bromobutane
5. Toluene reacts with a halogen in the presence of iron (III) chloride giving ortho and para halo compounds. The [1]
reaction is

a) Nucleophilic substitution reaction b) Free radical addition reaction

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c) Electrophilic elimination reaction d) Electrophilic substitution reaction
6. IUPAC name of (CH3)3CCl is: [1]

a) n – butyl chloride

c) t – butyl chloride
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b) 3 – chloro butane

d) 2-chloro, 2-methyl propane

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7. The preparation of alkyl chloride is carried out by: [1]

a) constant boiling of alcohol with HCl. b) passing dry hydrogen chloride gas through a
solution of alcohol.
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c) heating alcohol with potassium chloride. d) heating alcohol with sodium chloride.
8. Which one of the following is a synthetic halogen compound? [1]
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a) Chloramphenicol b) Diphenyl hydramine

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c) Chloroquine d) Omeprazole
9. Which one of the following is employed as antityphoid drug? [1]

a) Diphenyl hydramine b) Chloramphenicol

c) Omeprazole d) Chloroquine
10. Racemisation occurs in: [1]

a) SN1 reaction b) SN2 reaction as well as SN1 reaction

c) Neither SN2 nor SN1 reactions d) SN2 reaction

11. In which of the following molecules carbon atom marked with an asterisk (*) is asymmetric? [1]

a.

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 b.

c.

d.

a) (b), (c), (d) b) (a), (b), (c)

c) (a), (b), (c), (d) d) (a), (c), (d)

12. Which branched chain isomer of the hydrocarbon with molecular mass 72u gives only one isomer of [1]
monosubstituted alkyl halide?

a
a) Tertiary butyl chloride b) Neohexane

tan
c) Isohexane d) Neopentane
13. Write the structure of the major organic product in the following reaction: [2]
water

C H3 C H(Br)C H2 C H3 + N aOH −−−→

ha
14. How will you bring the conversion? [2]
Propene to 1-nitropropane
vk

15. Convert 1 - butene to 1 — chlorobutane. [2]

16. Draw the structure of the major monohalo product in the following reaction : [2]
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17. Write balanced equation for the following: [2]

Ga

i. When chloroform is oxidized by air

ii. Chloroform reacts with chlorine.
[3]
18. a. Out of and

which one is more reactive towards SN2 reaction and why?

b. Out of and

which one is more reactive towards nucleophilic substitution reaction and why?

c. Out of and

which one is optically active and why?

19. Complete the following reaction: [3]

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 +
H , H2 O

A −−−−−→ B ​

20. Out of C6H5CH2Cl, and C6H5CHClC6H5, which is more easily hydrolysed by aqueous KOH? [3]

21. Discuss the role of Lewis acids in the preparation of aryl bromides and chlorides in the dark. [3]
22. Write the structures of the following organic halogen compounds. [3]
i. 2-(2-Chlorophenyl)-1-iodooctane
ii. 2-Bromobutane
iii. 4-tert-Butyl-3-iodoheptane
23. Diphenyls are potential threat to the environment. How are these produced from arylhalides? [5]
24. Explain why [5]
i. alkyl halides, though polar, are immiscible with water?
ii. Grignard's reagent should be prepared under anhydrous conditions?

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25. Why are aryl halides less reactive towards nucleophilic substitution reactions than alkyl halides? How can we [5]
enhance the reactivity of aryl halides?

ata
kh
u rav
Ga

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