Question

Predict the major product obtained upon radical bromination of t-butylcyclohexane.

3-bromo-1-tert-butylcyclohexane
4-bromo-1-tert-butylcyclohexane
2-bromo-1-tert-butylcyclohexane
1-bromo-1-tert-butylcyclohexane
1-bromo-1,1-dimethylethylcyclohexane

Answer 1

1-bromo-1-tert-butylcyclohexane

Step-by-step explanation:

The parent compound comprises of a cyclohexane to with a tertiary butyl carbon attached. We have been told that the reaction occurs by radical mechanism hence we must recall the order of stability of radicals: tertiary>a secondary> a primary. This implies that the reaction will occur at carbon 1 of the cyclohexane which is a tertiary carbon atom. This leads to the formation of a radical at the 1-position and bromination at that position hence the answer chosen above.