Q17-71E - Organic Chemistry (Mcmurry)

Question

A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate:

Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:

Step-by-Step Solution

Answer

The mechanism of the reaction is;

Step1: Use of ethyl acetate

One of the short-chain esters, ethyl acetate is frequently utilized in the food, beverage, and solvent industries. Currently, energy-intensive and unsustainable technologies based on natural gas and crude oil are used to produce ethyl acetate.

There have been significant attempts made to increase the synthesis of ethyl-acetate by engineering yeast strains since it is crucial for the flavor and fragrance of alcoholic drinks.

Step2: Mechanism to account for the formation of ethyl acetate

The mechanism of the reaction is;