Ethanoic acid to methanamine
2 steps: condensation, then Hoffmann bromamide degradation
Ethanoic acidCH₃COOHCarboxylic acid - Step 1
NH₃, then heat
EthanamideCH₃CONH₂Amide - Step 2
Br₂ + NaOH(aq)
MethanamineCH₃NH₂Amine
Exam answer
- Step 1: Ethanoic acid to ethanamide: NH₃, then heat.
- Step 2: Ethanamide to methanamine: Br₂ + NaOH(aq).
Alternative routes (3)
- Ethanoic acid → Ethanoyl chloride → Ethanamide → Methanamine
- Ethanoic acid to ethanoyl chloride: SOCl₂.
- Ethanoyl chloride to ethanamide: NH₃.
- Ethanamide to methanamine: Br₂ + NaOH(aq).
- Ethanoic acid → Ethanoic anhydride → Ethanamide → Methanamine
- Ethanoic acid to ethanoic anhydride: conc. H₂SO₄ (or P₂O₅), heat.
- Ethanoic anhydride to ethanamide: NH₃.
- Ethanamide to methanamine: Br₂ + NaOH(aq).
- Ethanoic acid → Ethanoyl chloride → Ethanoic anhydride → Ethanamide → Methanamine
- Ethanoic acid to ethanoyl chloride: SOCl₂.
- Ethanoyl chloride to ethanoic anhydride: CH₃COONa (sodium ethanoate).
- Ethanoic anhydride to ethanamide: NH₃.
- Ethanamide to methanamine: Br₂ + NaOH(aq).
Reagent and reason, step by step
- Step 1: Ethanoic acid to ethanamide: NH₃, then heat The acid first forms ammonium ethanoate, which loses water on heating.
- Step 2: Ethanamide to methanamine: Br₂ + NaOH(aq) Hoffmann bromamide degradation: the amine has one carbon less than the amide.
Ethanoic acid to methanamine: quick answers
How many steps does it take to convert ethanoic acid to methanamine?
2 steps: Ethanoic acid, then ethanamide, then methanamine.
Which named reaction is used to convert ethanoic acid to methanamine?
Hoffmann bromamide degradation. An amide treated with bromine and aqueous or alcoholic NaOH gives a primary amine with one carbon atom fewer.
What is the reagent for step 1 of ethanoic acid to methanamine?
Ethanoic acid to ethanamide: NH₃, then heat. The acid first forms ammonium ethanoate, which loses water on heating.