Question 12 of 20advanced🔧 ApplyLong Answer5 marks

How will you convert: (i) Ethanoic acid into methanamine (ii) Hexanenitrile into 1-aminopentane (iii) Methanol to ethanoic acid (iv) Ethanamine into methanamine (v) Ethanoic acid into propanoic acid (vi) Methanamine into ethanamine (vii) Nitromethane into dimethylamine (viii) Propanoic acid into ethanoic acid?

(i)
Answer

Ethanoic acid is first converted to ethanamide by reaction with ammonia, then ethanamide is converted to methanamine by Hoffmann bromamide reaction (reaction with Br₂ and NaOH).

(ii)
Answer

Hexanenitrile is hydrolysed to hexanoic acid, which is then converted to hexanamide by reaction with ammonia. Hexanamide undergoes Hoffmann bromamide reaction to give 1-aminopentane.

(iii)
Answer

Methanol is oxidised to methanal (formaldehyde) using oxidising agents. Methanal is then converted to ethanoic acid through appropriate carbon-chain elongation reactions followed by oxidation.

(iv)
Answer

Ethanamine is converted to ethanamide by acylation. Ethanamide then undergoes Hoffmann bromamide reaction to yield methanamine (loss of one carbon atom).

(v)
Answer

Ethanoic acid is reduced to ethanol using LiAlH₄. Ethanol is converted to ethyl halide, which reacts with KCN to form propionitrile. Hydrolysis of propionitrile yields propanoic acid.

(vi)
Answer

Methanamine is treated with nitrous acid (HNO₂) to form methanol. Methanol is converted to methyl halide, which reacts with KCN to give ethanenitrile. Reduction of ethanenitrile yields ethanamine.

(vii)
Answer

Nitromethane is reduced to methanamine. Methanamine is then methylated using methyl iodide (CH₃I) or through reaction with formaldehyde and formic acid to give dimethylamine.

(viii)
Answer

Propanoic acid is converted to propanamide by reaction with ammonia. Propanamide undergoes Hoffmann bromamide reaction to give ethanamine. Ethanamine is treated with nitrous acid to give ethanol, which is oxidised to ethanoic acid.

Explanation

These conversions involve key organic reactions including Hoffmann bromamide reaction (which converts amides to primary amines with one less carbon), hydrolysis of nitriles, reduction reactions, oxidation reactions, and diazotisation. The Hoffmann bromamide reaction is particularly important for reducing carbon chain length by one carbon while converting amides to amines.