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Reactions of Acyl Chlorides
Reactions with –OH groups

Water
Acyl chloride + Water  Carboxylic Acid + Hydrochloric Acid

Ethanoyl chloride + Water  Ethanoic Acid + Hydrochloric Acid
HCl fumes are steamy and acidic
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Methanol
Acyl chloride + Methanol  Ester + Hydrochloric Acid
Ethanoyl chloride +Methanol  Methyl ethanoate + Hydrochloric Acid

Irreversible and occurs at room temperature- can more easily get a 100% conversion than the
alternative option using carboxylic acid and alcohol which requires heat, catalyst and is reversible
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Also ethanoic acid is produced rather than HCl
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g
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g
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Acid Anhydrides and Acyl Chlorides are bothe extremely reactive towards nucleophiles which have a
lone pair of electrons
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Both acid anhydrides and acyl chlorides will react with water, alcohols, ammonia and amines to give
a range of synthetically useful products
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1) Attraction; The δ+ carbon of the polar C=O bond attracts the lone pair of a nucleophile
2) Addition; Lone pair of nucleophile forms a new bond to carbon, producing a saturated ion
that has both positive and negative charges
3) Elimination; C-Cl of the acyl chloride or the C-O of the anhydride breaks, liberating a Cl- ion or
A- ion as the C=O bond simultaneously reforms
4) Deprotonation; new compound is formed by removal of a proton by basic ammonia
Generally Acid Anhydrides are better acylating reagents than Acyl Chlorides;
 Cheaper to produce
 Less reactive- Reactions more easily controlled
 Less corrosive as Acyl Chloride reactions produce a strong acid, HCl



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