Problems and exercisesUsefulness of halogenation

1. A single product?

Which of these alkanes give a single monochlorinated derivative and are therefore good substrates for halogenation?

1. Ethane
2. Propane
3. Cyclohexane
4. 2,2-Dimethylpropane
5. Pentane

2. Avoiding polyhalogenation

Chlorinating methane also gives CH₂Cl₂, CHCl₃ and CCl₄. How can the formation of CH₃Cl be favoured?

3. Selective bromination

What major product is obtained by brominating 2-methylpropane with light? Why?

4. Initiators and reagents

What is benzoyl peroxide used for in a halogenation? What advantage do N-bromosuccinimide and sulfuryl chloride have over the halogens?