Acyl Chlorides & Esters
Acyl groups
- Acyl groups can be built into many molecules using acyl chlorides or acid anhydrides (known as acylating agents)
- Acyl chlorides are derivatives of carboxylic acids by substitution of the -OH group by a chlorine atom
- Acyl chlorides are named by identifying the parent hydrocarbon chain and adding the suffix -oyl chloride
- They can also be named by removing the -oic acid from the carboxylic acid and adding -oyl chloride
- Acid anhydrides are also derivatives of carboxylic acids formed by substitution of the -OH group by an alkanoate
- Acid anhydrides are named by identifying the parent hydrocarbon chain and adding the suffix -oic anhydride
- They can also be named by removing the -oic acid from the carboxylic acid and adding -oic anyhydride
Ethanoic acid derivatives
Worked example
Draw the displayed formula for the following:
A. Butanoyl chloride
B. Butanoic anhydride
Answer:
- Acyl chlorides are reactive organic compounds that undergo many reactions such as nucleophilic addition-elimination reactions
- In nucleophilic addition-elimination reactions, the nucleophilic addition of a small molecule across the C=O bond takes place followed by elimination of a small molecule
- Examples of these nucleophilic addition-elimination reactions include:
- Hydrolysis
- Reaction with alcohols to form esters
- Reaction with ammonia and primary amines to form amides
Hydrolysis
- The hydrolysis of acyl chlorides results in the formation of a carboxylic acid and HCl molecule
- This is a nucleophilic addition-elimination reaction
- A water molecule adds across the C=O bond
- A hydrochloric acid (HCl) molecule is eliminated
- An example is the hydrolysis of propanoyl chloride to form propanoic acid and HCl
Acyl chlorides are hydrolysed to carboxylic acids
Formation of esters
- Acyl chlorides can react with alcohols to form esters
- The esterification of acyl chlorides is also a nucleophilic addition-elimination reaction
- The alcohol adds across the C=O bond
- A HCl molecule is eliminated
Acyl chlorides undergo esterification with alcohols to form esters
Formation of amides
- Acyl chlorides can form amides with primary amines and concentrated ammonia
- The nitrogen atom in ammonia and primary amine has a lone pair of electrons which can be used to attack the carbonyl carbon atom in the acyl chlorides
- The product is an amide (when reacted with ammonia) or N-substituted amide (when reacted with primary amines)
- This is also an example of a nucleophilic addition-elimination reaction as
- The amine or ammonia molecule adds across the C=O bond
- A HCl molecule is eliminated
Acyl chlorides undergo reactions with ammonia and primary amines to form amides
