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14.10: Acid Halides to Carboxylic Acids: Hydrolysis

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JoVE Core
Organic Chemistry

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Acid Halides to Carboxylic Acids: Hydrolysis
 
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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. 

Figure1

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.

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Keywords: Acid Halides Carboxylic Acids Hydrolysis Nucleophilic Acyl Substitution Tetrahedral Intermediate Carbonyl Carbon Halide Ion Strong Acid Base Catalyst Pyridine Pyridinium Chloride

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