Question

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

a) 1-Bromo-t-butylcyclohexane
b) 1-Bromo-4-t-butylcyclohexane
c) 1-Bromo-2-t-butylcyclohexane
d) 1-Bromo-3-t-butylcyclohexane

Answer 1

The major product obtained upon radical bromination of t-butylcyclohexane is 1-Bromo-4-t-butylcyclohexane (b).

Step-by-step explanation:

The major product obtained upon radical bromination of t-butylcyclohexane is 1-Bromo-4-t-butylcyclohexane (b).

When a radical bromination reaction occurs on a t-butyl group, the hydrogen atoms are abstracted from the tertiary carbon (C4) due to the high degree of stability of the resulting t-butyl radical. This results in the substitution of the hydrogen atom with a bromine atom.

Therefore, the major product will have the bromine atom attached to the C4 position of the cyclohexane ring, and there will be no other bromine substitutions on the ring.