Question Detail
Question
Predict the two most likely mechanisms which occur when 2-iodohexane is heated in ethanol.
Correct Answer
Option D is the correct answer.
Detailed Explanation
When 2-iodohexane is heated in ethanol (a polar protic solvent, weak nucleophile, weak base), it undergoes solvolysis via SN1 and elimination via E1. The weak nucleophile/base and formation of a carbocation intermediate favor both SN1 and E1.
Hint
What mechanisms are favored with a weak nucleophile and polar protic solvent?