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14.10: Acid Halides to Carboxylic Acids: Hydrolysis

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Organic Chemistry

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Acid Halides to Carboxylic Acids: Hydrolysis

14.10: Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.

As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid as the substitution product. 


The reaction produces a very strong acid, HCl, as a by-product. Therefore, a base such as pyridine is used in the reaction, which reacts with HCl to form pyridinium chloride. This process neutralizes the acid and prevents undesired side reactions.


Acid Halides Hydrolysis Nucleophilic Acyl Substitution Reaction Carboxylic Acids Water Catalyst Mechanism Tetrahedral Intermediate Carbon-oxygen Bond Halide Ion Proton Transfer Substitution Product Strong Acid HCl By-product Base Catalyst Pyridine Pyridinium Chloride Neutralizes

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