When a chlorine atom is connected instead of OH bond in carboxylic acid it's called carboxylic acid chloride. In this tutorial we talk about preparing, reactions and physical properties of carboxylic acid chloride compounds.
Examples of 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 hydrolysis easily and in the water and give carboxylic acid and HCl as products. We know carboxylic acid is a weak acid and HCl is a strong acid.
Due to formation of strong acid and a weak acid, pH value of solution become a less value (below than 7).
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.This is the hydrolysis of carboxylic acid chloride. Next, these two acids react with NaOH and form salts of two acids (NaCl, CH3COO-Na+).
Carboxylic acid chloride reacts with ammonia or ammine and give amides. According to the amine types (primary, secondary or tertiary), type of amide is changed.
Carboxylic acid chloride and ammonia react and give amide.
Carboxylic acid chloride and primary amine react and give substituted amide.
Acid halide and secondary amine react and give substituted amide.
Carboxylic acid chloride and tertiary ammine do not react.
Carboxylic acid chloride reacts with excess grignard reagent and give tertiary alcohols. Two grignard molecules are added to the carbon atom which is in carboxylic acid chloride group. Water should be added after grignard applying. In this reaction, grignard acts as nucleophile.
Alkyl part of grignard attacks the carbon atom which is in carboxylic acid chloride group
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.