Radical Selectivity Practice Problems

Use the bond-dissociation energies from the given table to determine whether the chlorination of propane would be selective or not.

For the synthesis of 2-halopropane, would it be better to perform chlorination or bromination of propane? Explain.

The relative rate of formation of a tertiary, a secondary, and a primary alkyl radical by a chlorine radical is 5 : 3.8 : 1 at room temperature. However, the relative rates for the formation of these radicals decrease when we increase the reaction temperature. Explain this decrease in the degree of regioselectivity.

Show the major products of free-radical bromination for each of the compounds given below. Keeping in mind that the bromination is highly selective towards the stable radical formation.

a. Methylcyclohexane
b. Cyclopentane

Show the major products of free-radical bromination of the given compound below. Keeping in mind that bromination is highly selective towards the stable radical formation.

iso-Propyl benzene