UNIT – 10 HALOALKANES AND HALOARENES

SAMPLE QUESTIONS

1. Give reasons for the following:

i) Chloroethane is insoluble in water.

ii) Thionyl chloride method is preferred for preparing alkyl chlorides from alcohols.
iii) Chloroform is stored in closed dark coloured bottles completely filled so that air
is kept out.
iv) C – Cl bond length in chlorobenzene is shorter than C – Cl bond length in CH 3 – Cl
v) SN1 reactions are accompanied by racemisation in optically active alkylhalides.
vi) Benzyl chloride is highly reactive towards the SN1 reaction.
vii) 2-bromobutane is optically active but 1-bromobutane is optically inactive.
viii) Electrophilic reactions in haloarenes occur slowly.
ix) The treatment of alkyl chloride with aqueous KOH leads to the formation of
alcohol but in the presence of alcoholic KOH , alkene is the major product.
x) The presence of NO2 group at o/p position increases the reactivity of haloarenes
towards nucleophilic substitution reactions.
xi) N-Butyl bromide has higher boiling point than t-butyl bromide.
xii) Racemic mixture is optically inactive.
xiii) P-dichlorobenzene has higher melting point than those of o- and m- isomers.

2. Out of SN1 and SN2 , which reaction occurs with

a) Inversion of configuration
b) Racemisation
3. What happens when bromine attacks CH2 = CH - CH2-C ≡ CH
4. Out of chlorobenzene and cyclohexyl chloride, which one is more reactive towards
nucleophilic substitution reaction and why?
5. Why is t-butyl bromide more reactive towards SN1 reactions as compared to n-butyl
bromide?
6. Explain why:
1. the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride?
2. Grignard reagents should be prepared under anhydrous conditions?
7. An optically active compound having molecular formula C 7H15Br reacts with aqueous KOH
to give a racemic mixture of products. Write the mechanism involved in this reaction.
8. Following compounds are given to you:
2-bromopentane, 2-bromo-2-methylbutane, 1-bromopentane
i) Write the compound which is most reactive towards SN2 reaction.
ii) Write the compound which is optically active.
iii) Write the compound which is most reactive towards beta elimination reaction.

9. Among all the isomers of molecular formula C 4H9Br, identify

a) the one isomer which is optically active.
b) the one isomer which is highly reactive towards SN2
c) the two isomers which give same product on dehydrohalogenation with
alcoholic KOH.

10. Among the isomeric alkanes of molecular formula C 5H12, Identify the one that on
photochemical chlorination yields

a) A single monochloride
b) Three isomeric monochlorides
c) Four isomeric monochlorides

11. Which one of the following compounds is more easily hydrolysed by KOH and why?

CH3CHClCH2CH3 or CH3CH2CH2Cl

12. Although chlorine is an electron withdrawing group, yet it is ortho, para directing in
electrophilic aromatic substitution reactions. Why?