Carboxylic acid chloride preparing, reactions, physical properties

When a Cl atom is connected instead of OH bond in carboxylic acid it's called carboxylic acid chloride. In this tutorial we talk about preparing and reactions of carboxylic acid chloride compounds.


Examples of acid chloride

example of acid chloride

Chemical properties of Carboxylic acid chloride

Carboxylic acid chloride show different types of reactions such as an acid and to extend the carbon chain. But reactions of carboxylic acid chloride differ from carboxylic acids. The carbon atom which is linked with Cl atom is positively charged. Therefore carboxylic acid chloride mostly show Nucleophilic substitution reactions.

Carboxylic acid chloride and water

Carboxylic acid chloride hydrolysis easily and in the water and give carboxylic acid and HCl.

Carboxylic acid chloride and water


Carboxylic acid chloride aqueous solution

Carboxylic acid chloride aqueous solution


Strong aqueous bases and Carboxylic acid chloride

Some strong bases are NaOH and KOH. This reaction gives, salt of carboxylic acid, salt related to base and water. This rection release a large heat.
First, carboxylic acid chloride reacts with water and produce two acids, CH3COOH and HCl. Next, these two acids react with NaOH.

NaOH and acid chloride reaction


Carboxylic acid chloride and ammonia,ammine

Carboxylic acid chloride reacts with ammonia or ammine and give amides. According to the amine types, type of amide is changed.


With ammonia

Carboxylic acid chloride and ammonia react and give amide.

acid chloride and ammonia

With primary ammine

Carboxylic acid chloride and primary amine react and give substituted amide.

acid chloride and primary ammine

With secondary ammine

Acid halide and secondary amine react and give substituted amide.

acid chloride and secondary ammine

With tertiary ammine

Carboxylic acid chloride and tertiary ammine do not react.



With grignard reagent reaction

Carboxylic acid chloride reacts with excess grignard reagent and give tertiary alcohols. Two grignard moles are added to carboxylic acid carbon. Water should be added after grignard applying. In this reaction, grignard acts as nucleophile.

acid halide and grignard reaction


Questions of carboxylic acid chlorides


How to separate ethanoyl chloride and benzoyl chloride?

Ethanoyl chloride and benzoyl chloride are added to water separately. A white precipitate forms in one solution. The precipitate is benzoic acid. In other solution, ethanoic acid is given.


Ethanoyl chloride and water reaction

ethanoyl chloride and water reaction

Benzoyl chloride and water reaction

benzoyl chloride and water reaction


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