18-18-7P b - Organic Chemistry (Mcmurry)

Question

Predict the products of the following reactions:

Step-by-Step Solution

Answer

b) The product of the reaction is,

Ether cleavage reaction

In an ether cleavage reaction, if ether is present with only primary and secondary alkyl groups, the cleavage occurs by S_N2 attack of a nucleophile. This S_N2 attacks at the less hindered alkyl group.

The product of the reaction

b) 

The first step is the identification of the substitution pattern of the ether. A primary alkyl group is present on one side of the ether oxygen, and on the other side is the secondary alkyl group. The bromide ion attacks the less hindered primary group and forms bromopropane. The oxygen atom remains with the secondary alkyl group and forms secondary alcohol.