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14.11: Acid Halides to Esters: Alcoholysis

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JoVE Core
Organic Chemistry

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Acid Halides to Esters: Alcoholysis
 
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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.

Figure1

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.

Figure2

Tags

Acid Halides Esters Alcoholysis Nucleophilic Acyl Substitution Reaction Alcohol Alcohol As Nucleophile Mechanism Tetrahedral Intermediate Carbonyl Chloride Ion Ester As Final Product H3O+ Byproduct Pyridine Base Sulfonyl Chlorides Sulfonic Acid Esters

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