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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

Keywords: Alcoholysis Nucleophilic Acyl Substitution Acid Halides Esters Tetrahedral Intermediate Carbonyl Chloride Ion Proton Pyridine Sulfonyl Chlorides Sulfonic Acid Esters

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