Login processing...

Trial ends in Request Full Access Tell Your Colleague About Jove

14.11: Acid Halides to Esters: Alcoholysis

JoVE Core
Organic Chemistry

A subscription to JoVE is required to view this content.
You will only be able to see the first 20 seconds.

Acid Halides to Esters: Alcoholysis

14.11: Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:

  1. First, the alcohol acts as a nucleophile and attacks the acyl carbon to form a tetrahedral intermediate.
  2. Next, the carbonyl re-forms with the loss of a chloride ion.
  3. Lastly, the positively charged intermediate loses a proton to give an ester as the final product along with H3O+, making HCl an overall byproduct of the reaction.


Pyridine is used as a base to neutralize the acidic reaction mixture.

Alcoholysis of sulfonyl chlorides follows a similar pattern and forms sulfonic acid esters.


Get cutting-edge science videos from JoVE sent straight to your inbox every month.

Waiting X
Simple Hit Counter