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Chapter 14: Carboxylic Acid Derivatives Back To Chapter

14.11: Acid Halides to Esters: Alcoholysis

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Acid Halides to Esters: Alcoholysis

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14.10: Acid Halides to Carboxylic Acids: Hydrolysis

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Just like acid halides react with water to form carboxylic acids, they react with alcohol to produce esters in an analogous reaction called alcoholysis.

As acid halides are the most reactive acyl derivatives, alcoholysis does not require an acid or a base catalyst.

The first step of the mechanism involves a nucleophilic attack by the alcohol at the carbonyl carbon, forming a tetrahedral intermediate.

In the next step, the carbon–oxygen double bond is re-formed with the departure of a halide ion as the leaving group.

Lastly, deprotonation gives an ester as the final product.

With acid chlorides, HCl is formed as a by-product. So, pyridine is added to neutralize the HCl and prevent unwanted side reactions.

Additionally, the reaction outcome is influenced by steric factors. For example, if the alcohol has primary and secondary hydroxyl groups, the unhindered primary alcohol is selectively esterified over the hindered secondary alcohol.

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:

First, the alcohol acts as a nucleophile and attacks the acyl carbon to form a tetrahedral intermediate.
Next, the carbonyl re-forms with the loss of a chloride ion.
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.

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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