Acyl chlorides
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What is an acyl chloride?
A derivative of carboxylic acids where the OH is replaced by Cl
How are acyl chlorides made?
Reacting carboxylic acid with thionyl chloride (SOCl2) —> Acyl chloride + sulfur dioxide + hydrogen chloride Observation: fumes of HCl CH3CH2COOH + SOCl2 —> CH3CH2COCl + SO2 + HCl
Why should water not be present when makig acyl chlorides?
Because acyl chlorides are very reactive and react with water to make carboxylic acids CH3CH2COCl + H2O —> CH3CH2COOH + HCL
What can acyl chlorides be used to make?
They are excellent chemicals for organic synthesis. - Esters, especially phenyl esters which can’t be made using carboxylic acids. - Carboxylic acids - Primary and Secondary amides
How do acyl chlorides make primary amides?
Acyl chloride + ammonia —> primary amide and HCl
How do acyl chlorides make secondary amides?
Acyl chloride + amine —> secondary amide + hydrogen chloride