Topic B6: Carboxylic Acids
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Give 3 carboxylic acid derivatives
-esters -acyl chlorides -acid anhydrides
What is esterification?
reaction of an alcohol with a carboxylic acid to form an ester
Conditions of esterification
-warm alcohol and carboxylic acid (in water bath) -add conc. sulfuric acid (catalyst)
General equation for esterification
carboxylic acid + alcohol —> ester + water
What is hydrolysis?
chemical breakdown of a compound in the presence of water or an aqueous solution
Conditions for acid hydrolysis of esters
-heat ester under reflux -add dilute aqueous acid (acid = catalyst, water = breaks ester down)
Is alkaline hydrolysis reversible?
no
Conditions for alkaline hydrolysis
-ester is heated under reflux -add aqueous hydroxide ions
How do you prepare acyl chlorides?
carboxylic acid + SOCl2 (thionyl chloride)
Products of acyl chloride preparation
-acyl chloride -SO2 -HCl
Why are acyl chlorides important?
easily converted into carboxylic acid derivatives (e.g. esters, amides) and provides a good yield
Do acyl chlorides react with nucleophiles?
yes - by losing chloride ion and retaining C=O double bond
Acyl chloride + alcohol —->
ester + HCl
Acyl chloride + phenol —>
phenyl ester + HCl
Acyl chloride + water —>
carboxylic acid + HCl
Acyl chloride + ammonia —>
primary amide + ammonium chloride
Acyl chloride + primary amine —>
secondary amide
Observations of acyl chloride + water reaction
-dense, steamy hydrogen chloride fumes released -vigorous reaction