Amide formation
Ammonia attacks the carbonyl carbon and chloride leaves when the tetrahedral intermediate collapses. Deprotonation gives acetamide, while another ammonia equivalent neutralises the acid to form ammonium chloride.
- Reagents
- Excess NH3
- Conditions
- Controlled addition with ammonia
- Reaction class
- Amide formation
- Equation
- CH3COCl + 2NH3 -> CH3CONH2 + NH4Cl
Overview
Ammonia attacks the carbonyl carbon and chloride leaves when the tetrahedral intermediate collapses. Deprotonation gives acetamide, while another ammonia equivalent neutralises the acid to form ammonium chloride.
Transformation
- Equation
- CH3COCl + 2NH3 -> CH3CONH2 + NH4Cl
- Reactants
- Acetyl chloride + 2 Ammonia
- Products
- Acetamide + Ammonium chloride
- Reagents
- Excess NH3
- Environment
- Controlled addition with ammonia
- Reaction class
- Amide formation
- Mechanism
- nucleophilic addition-elimination
- Evidence level
- source-backed molecular example
Scope and limitations
- Scope
- Ethanoyl chloride gives ethanamide (acetamide).
- Limitations
- Water competes as a nucleophile; excess ammonia also neutralises the acid by-product.
Related reactions
- Amide hydrolysis: Acetamide → Ethanoic acid
Acid activates the amide carbonyl for water addition. Proton transfer makes nitrogen a better leaving group before C-N cleavage; the acyl fragment becomes ethanoic acid and the nitrogen ends as ammonium.
References
- A-level Chemistry 7405: Organic chemistryAQA · AQA specification
Checked 2026-09-16. Supports A-level topic coverage, including acid anhydrides, acylation and aspirin, amines, amino acids, polymers, synthesis and analysis. Coverage varies by examination board.