Unit - 10–Haloalkanes and Haloarenes

Section A:
I] Multiple Choice Questions:

1. Which of the following is most reactive towards SN1 reaction?

(a) C6H5C(CH3)C6H5Br
(b) C6H5CH2Br
(c) C6H5CH(C6H5)Br
(d) C6H5CH(CH3)Br
2. Which one of the following forms propane nitrile as the major product?
a) Propyl bromide + aq KCN b) Ethyl bromide + aq KCN
c) Propyl bromide + aq AgCN d) Ethyl bromide + aq AgCN
3. A hydrocarbon C6H12 does not react with chlorine in dark but gives a single monochloro
compound C6H11Cl in bright sunlight. The hydrocarbon is
a) Cyclohexene b) Cyclohexyne
c) Hexane d) Cyclohexane
4. The most common method for preparing haloarene is by
a) Swarts reaction b) Fittig reaction
c) Sandmeyer’s reaction d) Wurtz reaction
5. Two possible stereo-structure of CH3—CH(OH)COOH which are optically active are called (a)
mesomers (b) enantiomers (c) diastereomers (d) atropisomers
6. The synthesis of alkyl fluoride is best accomplished by
(a) Finkelstein reaction (b) Swarts reaction (c) Free radical fluorination
(d) Sandmeyers reaction
7. What is ‘A’ in the following reaction? 

II] Assertion-reason questions:

In the following questions, a statement of assertion followed by a statement of reason is given.
Choose the correct answer out of the following choices.
(a) Assertion and reason both are correct statements and reason is the correct explanation for
assertion.
(b) Assertion and reason both are correct statements and reason is not the correct explanation for
assertion.
(c) Assertion is correct statement but reason is wrong statement.
(d) Assertion is wrong statement but reason is correct statement.

8. Assertion: Tert-butyl bromide undergoes SN1 nucleophilic substitution readily than n-butyl
bromide.
Reason: It proceeds by the formation of stable carbocation.
9. Assertion: Haloalkanes are immiscible in water.
Reason: Haloalkanes have both dispersion forces as well as dipole-dipole interactions between
molecules.
10. Assertion (A) : Presence of a nitro group at ortho or para position increases the reactivity of
haloarenes towards nucleophilic substitution. Reason (R) : Nitro group, being an electron
withdrawing group decreases the electron density over the benzene ring

Section B:
III] Read the given passages and answer the questions that follow:
The polarity of C—X bond is responsible for the nucleophilic substitution reactions of alkyl halides
which mostly occur by SN1 and SN2 mechanisms. The rates of SN1 reaction are governed by the
stability of intermediate carbocations while that of SN2 reactions are governed by steric factors.
Chirality has a great role in understanding the mechanism of SN1 and SN2 reactions. SN1 reactions
of chiral alkyl halides are accompanied by racemisation. Whereas SN2 reactions are characterized by
inversion of configuration.
Answer the following:

11. What do you mean by chirality?

12. In the pair, (CH3)3 C—Br and CH3—CH2—Br, which one is more reactive towards SN2
reaction and why
13. What is meant by the term racemic mixture?
14. Write the structural formulae of the organic compounds ‘A’, B’, ‘C’, and ‘D’ in the following
sequence of reaction:
❑
CH 3−CH Br−CH 2−CH 3 alc. KOH A Br 2 B alc . KOH C
→ → →
15. Convert:
(i) Aniline to Bromobenzene
(ii) Benzene to Diphenyl
(iii) Methanol to ethanenitrile
16. Write the structure of the major organic product in each of the following reactions:
C 2 H 5 ONa
(i) ( CH 3 )2 CH −CH ( Br ) CH 2 CH 3 →
ethanol /heat
(ii) CH 3 CH 2 Cl +SbF 3 heat
→

(iii) CH 3 CH 2 CH =CH 2 + HBr peroxide

→

17. Give reason:

(i) Chloroethane is insoluble in water.
(ii) Thionyl chloride method is preferred for preparing alkyl chlorides from alcohol
18. An organic compound ‘A’ having molecular formula C 4 H 8 on hydration with dil. H 2 SO 4 gives
’B’. ’B’ on treatment with conc. HCl and anhydrous ZnCl2 gives ‘C’ which on treatment with
alcoholic NaOH gives back ‘A’. Identify the compounds ‘A’, ‘B’ and ‘C’ and write the equations
involved.
19. Explain the following with the help of chemical equations:
(a) Finkelstein reaction
(b) Fittig reaction
20. How do you convert the following:
(i) Prop-1-ene to 1-fluoropropane
(ii) Chlorobenzene to 2-chlorotoluene
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