QUESTION BANK (Haloalkanes and Haloarenes)

1 What are ambident nucleophiles? Give an example. 2

2 In the following pairs of halogen compounds, which compound undergoes faster SN1 2
reaction?

3. Explain SN2 and SN1mechanism. 5

4. Draw the structures of major monohalo products in each of the following reactions: 6

5. Write the structure of the major organic product in each of the following reactions: 8

6. What happens when 6

(i) n-butyl chloride is treated with alcoholic KOH,
(ii) bromobenzene is treated with Mg in the presence of dry ether,
(iii) chlorobenzene is subjected to hydrolysis,
(iv) ethyl chloride is treated with aqueous KOH,
(v) methyl bromide is treated with sodium in the presence of dry ether,
(vi) methyl chloride is treated with KCN?
7. How the following conversions can be carried out? 5
(i) 1-Bromopropane to 2-bromopropane
 (ii) 2-Bromopropane to 1-bromopropane
(iii) Propene to 1-nitropropane
(iv) Toluene to benzyl alcohol
(v) Benzene to diphenyl
8. Primary alkyl halide C4H9Br (a) reacted with alcoholic KOH to give compound (b). 3
Compound (b) is reacted with HBr to give (c) which is an isomer of (a). When (a) is
reacted with sodium metal it gives compound (d), C8H18 which is different from the
compound formed when n-butyl bromide is reacted with sodium. Give the structural
formula of (a) and write the equations for all the reactions
9. Illustrate giving suitable example: 8
(i) Sandmeyer’s reaction
(ii) Finkelstein reaction
(iii) Swarts reaction
(iv) Wurtz reaction
(v) Fittig reaction
(vi) Wurtz fittig reaction
(vii) Friedel-Crafts reaction (Alkylation as well as acylation)
(viii) Saytzeff rule.
10. Accounts for the followings/ Explain why 10
(i) p-Dichlorobenzene has higher m.p than those of o- and m-isomers.
(ii) Dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.
(iii) Under SN1 conditions C6H5CHCl C6H5 gets hydrolysed more easily than
C6H5CH2Cl
(iv) Allylic and benzylic halides show high reactivity towards the SN1 reaction.
(v) Haloalkanes react with KNO2 to form alkyl nitrite as main product while
AgNO2 forms nitroalkane as the chief product.
(vi) The treatment of alkyl chorides with aqueous KOH leads to the formation of
alcohols but in the presence of alcoholic KOH, alkenes are major products.
(vii) Haloalkanes react with KCN to form alkyl cyanides as main product while
AgCN forms isocyanides as the chief product. Explain.
(viii) Haloarenes are extremely less reactive towards nucleophilic substitution
reaction than haloalkanes.
(ix) Alkyl halides, though polar, are immiscible with water?
(x) Grignard reagents should be prepared under anhydrous conditions.