Problem 725

Problem # 725

A chemist carried out a Fischer esterification using methanol that was isotopically labeled with ¹⁸O (indicated with an asterisk).

Which one of the esters below (A-D) was formed?

Solution

To answer this problem, you must be familiar with the nucleophilic acyl substitution mechanism.

In this mechanism, the nucleophile (methanol) becomes the -OCH₃ group in the ester.

At least 80% of second semester organic chemistry is two mechnanisms: nucleophilic acyl addition and nucleophilic acyl substitution. It's worth your time to become familiar with these mechanisms. See problems 705 (basic conditions), 706 (acidic conditions), 707, and 708.