Acetyl chloride

Acetyl chloride

3D model of acetyl chloride

A 25 ml bottle of acetyl chloride

Acetyl chloride is an organic compound with the formula CH₃COCl. It is a colorless, corrosive, volatile liquid. Acetyl chloride is a member of the acyl chloride family and is used as an important reagent in organic synthesis.

Structure and properties

Acetyl chloride consists of a carbonyl group (C=O) attached to a methyl group (CH₃) and a chlorine atom. The molecule is planar, and the carbonyl carbon is sp² hybridized. Acetyl chloride is highly reactive due to the presence of the electron-withdrawing chlorine atom, which makes the carbonyl carbon more electrophilic.

Preparation

Acetyl chloride can be prepared by the reaction of acetic acid with thionyl chloride (SOCl₂):

CH₃COOH + SOCl₂ _ CH₃COCl + SO₂ + HCl

This reaction is commonly used in laboratories to produce acetyl chloride.

Reactions

Acetyl chloride is a versatile reagent in organic chemistry. It is used to introduce the acetyl group into alcohols and amines to form esters and amides, respectively. For example:

• Reaction with alcohols:

ROH + CH₃COCl _ CH₃COOR + HCl

• Reaction with amines:

RNH₂ + CH₃COCl _ CH₃CONHR + HCl

Acetyl chloride also reacts with water to form acetic acid and hydrochloric acid:

CH₃COCl + H₂O _ CH₃COOH + HCl

Safety

Acetyl chloride is a corrosive and lachrymatory liquid. It should be handled with care, using appropriate personal protective equipment such as gloves and goggles. It reacts violently with water and should be stored in a dry environment.

Related pages

• Acyl chloride
• Acetic acid
• Thionyl chloride
• Organic synthesis