Chapter 14.17, Problem 39P

Interpretation Introduction

Interpretation:

Mechanism for proton exchange of an alcohol in an aqueous base has to be proposed.

Concept introduction:

Proton exchange basically means the transfer of a proton from one place to another in a molecule.  An acid or a base catalyze the reaction of exchange of protons.  For example, the rate of proton exchange of an alcohol is increased if a small amount of an acid or base is added to it.  A rapidly exchanged proton does not cause splitting and is observed as a singlet in the ${}^{\text{1}}\text{H NMR}$ spectrum.