• 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