Question

Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a solvent, or by distilling off the product as it forms. Draw curved arrows to show the movement of electrons in this step of the mechanism.

Answer 1

Answer:

See attachment for mechanism.

Explanation:

The Fischer esterification reaction is a nucleophilic substitution in the acyl group of a carboxylic acid, catalyzed by an acid.

1) The protonation of the oxygen of the carbonyl group activates the carboxylic acid...

2) ... against a nucleophilic attack by the alcohol, and produces a tetrahedral intermediate.

3) The transference of a proton from an oxygen atom to another produces a second tetrahedral intermediate and converts the -OH into a good leaving group.

4) The loss of a proton and the expulsion of H₂O regenerates the acid catalyzer and gives an ester as a product.