Chapter 11.6, Problem 11.7P

Interpretation Introduction

Interpretation:

Mechanism for the given reaction has to be proposed.

Concept Introduction:

Acid-catalyzed cleavage of ethers: Cleavage of ether requires both a strong acid and good leaving group. Mechanism of acid-catalyzed cleavage of dialkyl ethers depends on the nature of the carbons bonded to oxygen.

Step 1: Add proton (proton transfer from the acid catalyst to the oxygen atom of ether gives oxonium ion.

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation). Nucleophilic attack and the elimination of leaving group occurs simultaneously forming stable carbocation.