Chapter : Haloalkanes and haloarenes
1. Which of the following is an example of vic-dihalide?
(A) Dichloromethane (B) 1,2-dichloroethane (C) Ethylidene chloride (D) Allyl chloride
2. Toluene reacts with a halogen in the presence of iron(III) chloride giving ortho and para halo
compounds. The reaction is ______ .
(A) Electrophilic elimination reaction (B) Electrophilic substitution reaction
(C) Free radical addition reaction (D) Nucleophilic substitution reaction
3. The best reagent for preparation of haloalkanes from alcohols is
(A) Br2/red P (B) NaBr/H2SO4 (C) SOCl2 (D) PCl5
4. The optically active compound will be:
(A) 2-Chlorobutane (B) 1-Chlorobutane (C) 1-Chloropropane (D) Chloroform
5. The order of reactivity towards SN2 mechanism is :
(A) Primary halide<secondary halide<tertiary halide
(B) Secondary halide<primary halide<tertiary halide
(C) tertiary halide<secondary halide<primary halide
(D) primary halide<tertiary halide<secondary halide.
6. What is Saytzeff rule? Explain with the help of an example.
7. Show the mechanism of attack of sodium hydroxide on tert-Butyl bromide.
8. Write: (i) Fittig reaction (ii) Sandmeyer reaction
9. Write the following conversions:
(i) Chloroethane to butane
(ii) 2-Bromopropane to 1-bromopropane
(iii) Benzene to 4- bromonitrobenzene
10. Complete the following reactions:
(i) CH3-CH2OH + Br2/red P →
(ii) CH2=CH2 + Br2 (in the presence of CCl4 )→
(iii) CH3-CH=CH2 + Br2 (in presence of peroxide) →
11. What happens when
(i) bromobenzene is treated with alcoholic KOH.
(ii) methyl chloride is treated with KCN
(iii) ethyl chloride is treated with aqueous KOH
12. Give reasons:
(i) Grignard reagent should be prepared under anhydrous condition.
(ii) Reaction of alkyl halide with silver cyanide gives alkylisocyanide.
(iii) The dipole moment of alkyl halide is greater than aryl halide.
13. Substitution reactions involve the replacement of one atom or group (X) by another (Y):
RX + Y →RY + X
The halogenation of alkanes is a substitution reaction, in which a hydrogen atom is replaced by a
halogen atom.
Reactions of this type proceed by radical –chain mechanisms in which the bonds are broken and
formed by atoms or radicals as reactive intermediates. This mode of bond breaking , in which one
electron goes with R and the other with X , is called hemolytic bond fission.
(i) Which type of chemical species is formed by homolytic bond fission?
(ii) C6H5-CH3 + Cl2/sunlight→ ?
(iii) What is peroxide effect?
14. (a) Arrange each set of compounds in the order of increasing boiling points.
(i) Bromomethane, Bromoform, Chloroform, Dibromomethane
(ii) 1-Chloropropane, Isopropyl chloride, 1-Chlorobutane.
(b) Give reasons:
(i) n-Butyl bromide has higher boiling point than t-butyl bromide.
(ii) Racemic mixture is optically inactive.
(iii) The presence of nitro group at o/p positions increases the reactivity of haloarenes towards
nucleophilic substitution reactions.
15. (A) A hydrocarbon of molecular mass 72 g/mol gives a single monochloro derivative and two
dichloroderivatives on photochlorination. Give the structure of the hydrocarbon.
(B) Among all the isomers of molecular formula C4H9Br, identify
(i) the one isomer which is optically active.
(ii) the one isomer which is highly reactive towards SN2.
(iii) the two isomers which give same product on dehydrohalogenation with alcoholic KOH.
