Reaction of Alcohols With Acyl Chlorides
- Acyl chlorides are reactive organic compounds with a -COCl functional group
- The carbonyl carbon is electron-deficient and has a partial positive charge
- It is therefore susceptible to nucleophilic attack
- The carbon-chlorine bond breaks and white fumes of hydrogen chloride, HCl, are formed
Reaction with alcohols and phenols
- Acyl chlorides react with alcohols and phenols to form esters in a nucleophilic substitution reaction
- The -OH group acts as a nucleophile and attacks the carbonyl carbon to substitute the chlorine atom
- Forming esters from acyl chlorides rather than carboxylic acids is more effective because::
- Acyl chlorides are more reactive (so it produces the ester faster)
- Acyl chloride reactions go to completion (so more of the ester is produced)
Reaction with alcohols
- The reaction of acyl chlorides with alcohols is vigorous and white fumes of HCl gas are formed
Acyl chlorides react vigorously with alcohols to form esters
Reaction with phenols
- For the reaction of acyl chlorides with phenols to occur, heat and a base are required
- The base is needed to deprotonate the phenol and form a phenoxide ion
- The phenoxide ion is a better nucleophile than the original phenol molecule and will be able to attack the carbonyl carbon
Acyl chlorides react with phenols when heated and in the presence of a base to form esters
A base is needed to form a phenoxide ion which is a better nucleophile than phenol; now, nucleophilic attack on the carbonyl carbon can more readily occur
