PRACTICE QUESTIONS ON HALOALKANE:

1. A hydrocarbon C5 H12 gives only one monochlorination product. Identify the hydrocarbon.
2. Explain why is thionyl chloride method preferred for preparing alkyl chlorides from alcohols ?
3. How would you synthesize 1-bromobutane from but -1-ene in single step ?
4. Which is a better nucleophile – a bromide ion or an iodide ion ?
5. What happens when chlorine is passed through boiling toluene in the presence of sunlight ?
6. Under what conditions, 2 - methylpropene can be converted into isobutyl bromide by hydrogen
bromide ?
7. Suggest one convenient method for the synthesis of the following
• 1-Iodobutane from 1-butene
• sec-Propyl bromide from isobutyric acid
• Fluoroethane from ethanol
8. Explain why alcohols do not react with NaBr, but when H2SO4 is added, they form alkyl
bromides.
9. Explain why alkyl halides are generally not prepared in laboratory by free radical halogenation
of al- kanes.
10. Explain why free radical bromination of n-butane yield 2-bromobutane as the major product.
(a) What happens when
(i) Propene is treated with HBr in presence of peroxide,
(ii) N-Butane is reacted with HCl.
(iii) Chloropentane is treated with Na & Dry acetone in presence of NaI.
b) How can haloalkanes be prepared from
(i) alcohols
(ii) alkenes and
(iii) alkanes ?