Problems and exercisesHalogenation

1. Monochlorination products

How many different monochlorinated derivatives (not counting stereoisomers) are obtained by chlorinating each alkane?

1. Propane
2. Butane
3. 2-Methylpropane
4. 2,2-Dimethylpropane

2. Calculate the proportions

The relative reactivity of hydrogens towards chlorine is primary : secondary : tertiary = 1 : 4 : 5. Calculate the proportions of 1-chloropropane and 2-chloropropane in the chlorination of propane.

3. Chlorination of butane

With the same data, predict the proportions of 1-chlorobutane and 2-chlorobutane and compare them with the experimental ones (28% and 72%).

4. Chlorine versus bromine

In 2-methylbutane, chlorine gives four products in similar proportions, whereas bromine gives almost only (94%) 2-bromo-2-methylbutane. Which halogen is more selective? Why?