How will you convert:

Ethanamine into methanamine

Ethanamine into methanamine (ethylamine to methylamine)



Explanation: The structure of ethanamine is CH3CH2NH2. To convert ethanamine into methanamine (the number of carbon atoms is decreasing from two carbon atoms to one carbon atom), first we need ethanamide ( amide group- RCONH2) and we can get acetamide from acetic acid. By oxidation of ethanol, we can get ethanoic acid.


Step 1: Convert Ethanamine into ethanol with the help of diazonium salt


Ethanamine (CH3CH2NH2)reacts with NaNO2 and HCl to give Diazonium salt (R--N2+Cl-) which undergoes hydrolysis to form ethanol.


Note: The diazonium salts or diazonium compounds are the class of organic compounds with general formula R−N2+X where X is an organic or inorganic anion (for example, Cl, Br, BF4, etc.) and R is an alkyl or aryl group. Hence, they have two nitrogen atoms with one being charged. Example - Benzenediazonium chloride (C6H5N2+Cl)



Step 2: Convert ethanol to ethanoic acid by oxidation


Ethanol (CH3CH2OH) undergoes oxidation in the presence of strong oxidizing agent KMNO4 to form ethanoic acid (CH3COOH)


Step 3: Convert ethanoic acid into ethanamide (amide group)


Ethanoic acid (CH3COOH) is treated with ammonia (in excess) to form ethanamide (CH3CONH2)


Step 4: Convert ethanamide into methanamine by Hoffman Bromamide Reaction


Ethanamide (CH3CONH2) is treated with alc.NaOH or KOH in the presence of bromine, it gives methanamine (CH3NH2 - final product) which has one carbon atom less than the ethanamide.


6