How will you convert : (i) Ethanoic acid into methanamine (ii) He…

Question

How will you convert :
(i) Ethanoic acid into methanamine
(ii) Hexanenitrile into 1-aminopentane
(iii) Methanol to ethanoic acid
(iv) Ethanamine into methanamine

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Answer

(i) $\underset{\text { Ethanoic acid }}{ CH _3 COOH } \xrightarrow{ SOCl _2} \underset{\text { Ethanoyl chloride }}{ CH _3 COCl }$
$\xrightarrow{ NH _3 \text { (excess) }}$$\underset{\text { Ethanamide }}{CH _3 CONH _2}$
$\xrightarrow[\text { (Hoffmann bromide reaction) }]{ Br _2 / KOH }$$\underset{\text { Methanamined }}{CH _3 NH _2}$
(ii) $\underset{\text { Hexanenitrile }}{ CH _3\left( CH _2\right)_4 CN } \xrightarrow[\text { Hydrolysis }]{ H _3 O ^{+}}$$\underset{\text { Hexanoic acid}}{CH _3\left( CH _2\right)_4 COOH}$
$\underset{\text { Hexanoyl chloride }}{ CH _3\left( CH _2\right)_4 COCl } \xrightarrow{ NH _3 (excess)} CH _3\left( CH _2\right)_4 CONH _2$
$\xrightarrow[\text { (Hoffmann bromide reaction) }]{ Br _2 / KOH } \underset{\text { Pentanamine }}{ CH _3\left( CH _2\right)_4 NH _2}$
(iii) $\underset{\text { Methanol }}{ CH _3 OH } \xrightarrow{ PCl _5}$ $CHCl \xrightarrow{ KCN ( alc )}$ $\underset{\text { Ethanenitrile }}{ CH _3 CN}$
$\xrightarrow[\text { (Hydrolysis) }]{ H _3 O ^{+}} \underset{\text { Ethanoic acid }}{ CH _3 COOH }$
(iv) $CH _3 CH _2 NH _2 \frac{ HONO }{- N _2,- H _2 O } \rightarrow \underset{\text { Ethanol }}{ CH _3 CH _2 OH }$
$\xrightarrow[\text { (oxidation) }]{ K _2 Cr _2 O _7 / H _2 SO _4} \underset{\text { Acetaldehyde }}{ CH _3 CHO } \xrightarrow[\text { Oxidation }]{ K _2 Cr _2 O _7 / H _2 SO _4}$
$\underset{\text { Acetic acid }}{ CH _3 COOH } \xrightarrow{ NH _3}$$CH _3 COONH _4 \xrightarrow[- H _2 O ]{\Delta}$$CH _3 CONH _2$
$\frac{ Br _2 / KOH }{(\text { Hoffmann bromide reaction })} \rightarrow \underset{\text { Methanamine }}{ CH _3 NH _2}$

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