JEE Main & Advanced Chemistry Nitrogen Containing Compounds Some important conversions

(1) Conversion of methylamine to ethylamine (Ascent)

\[\underset{\text{Methylamine}}{\mathop{C{{H}_{3}}N{{H}_{2}}}}\,\xrightarrow{HN{{O}_{2}}}\underset{\text{Methyl alcohol}}{\mathop{C{{H}_{3}}OH}}\,\xrightarrow{P{{I}_{3}}}\underset{\text{Methyl iodide}}{\mathop{C{{H}_{3}}I}}\,\]\[\xrightarrow{NaCN}\underset{\text{Methyl cyanide}}{\mathop{C{{H}_{3}}CN}}\,\xrightarrow{LiAl{{H}_{4}}}\underset{\text{Ethylamine}}{\mathop{C{{H}_{3}}C{{H}_{2}}N{{H}_{2}}}}\,\]

(2) Conversion of ethylamine to methylamine (Descent)

\[\underset{\text{Ethylamine}}{\mathop{C{{H}_{3}}C{{H}_{2}}N{{H}_{2}}}}\,\xrightarrow{HN{{O}_{2}}}\underset{\text{Ethanol}}{\mathop{C{{H}_{3}}C{{H}_{2}}OH}}\,\underset{{{{K}_{2}}C{{r}_{2}}{{O}_{7}}}/{{{H}_{2}}S{{O}_{4}}}\;}{\mathop{\xrightarrow{[O]}}}\,\underset{\text{Acetaldehyde}}{\mathop{C{{H}_{3}}CHO}}\,\]\[\underset{{{{K}_{2}}C{{r}_{2}}{{O}_{7}}}/{{{H}_{2}}S{{O}_{4}}}\;}{\mathop{\xrightarrow{[O]}}}\,\underset{\text{Acetaldehyde}}{\mathop{C{{H}_{3}}CHO}}\,\xrightarrow{[O]}\underset{\text{Acetic acid}}{\mathop{C{{H}_{3}}COOH}}\,\xrightarrow{SOC{{l}_{2}}}\underset{\text{Acetyl chloride}}{\mathop{C{{H}_{3}}COCl}}\,\]

\[\xrightarrow{N{{H}_{3}}}\underset{\text{Acetamide}}{\mathop{C{{H}_{3}}CON{{H}_{2}}}}\,\underset{KOH}{\mathop{\xrightarrow{B{{r}_{2}}}}}\,\underset{\text{Methylamine}}{\mathop{C{{H}_{3}}N{{H}_{2}}}}\,\]

(3) Conversion of ethylamine to acetone

\[\underset{\text{Ethylamine}}{\mathop{{{C}_{2}}{{H}_{5}}N{{H}_{2}}}}\,\xrightarrow{HN{{O}_{2}}}\underset{\text{Ethyl  alcohol}}{\mathop{{{C}_{2}}{{H}_{5}}OH}}\,\underset{{{H}_{2}}S{{O}_{4}}}{\mathop{\xrightarrow{{{K}_{2}}C{{r}_{2}}{{O}_{7}}}}}\,\underset{\text{Acetaldehyde}}{\mathop{C{{H}_{3}}CHO}}\,\underset{{{H}_{2}}S{{O}_{4}}}{\mathop{\xrightarrow{{{K}_{2}}C{{r}_{2}}{{O}_{7}}}}}\,\underset{\text{Acetic acid}}{\mathop{C{{H}_{3}}COOH}}\,\xrightarrow{Ca{{(OH)}_{2}}}\underset{\text{Calcium acetate}}{\mathop{{{(C{{H}_{3}}COO)}_{2}}Ca}}\,\]\[\underset{\text{Acetaldehyde}}{\mathop{C{{H}_{3}}CHO}}\,\underset{{{H}_{2}}S{{O}_{4}}}{\mathop{\xrightarrow{{{K}_{2}}C{{r}_{2}}{{O}_{7}}}}}\,\underset{\text{Acetic acid}}{\mathop{C{{H}_{3}}COOH}}\,\xrightarrow{Ca{{(OH)}_{2}}}\underset{\text{Calcium acetate}}{\mathop{{{(C{{H}_{3}}COO)}_{2}}Ca}}\,\] \[\xrightarrow{heat}\underset{\text{Acetone}}{\mathop{C{{H}_{3}}COC{{H}_{3}}}}\,\]

(4) Conversion of propionic acid to

(i) Ethylamine, (ii) n-Butylamine.

(i) \[\underset{\text{Propionic aicd}}{\mathop{C{{H}_{3}}C{{H}_{2}}COOH}}\,\xrightarrow{SOC{{l}_{2}}}\underset{\text{Propionyl chloride}}{\mathop{C{{H}_{3}}C{{H}_{2}}COCl}}\,\xrightarrow{N{{H}_{3}}}\]\[\underset{\text{Propionamide}}{\mathop{C{{H}_{3}}C{{H}_{2}}CON{{H}_{2}}}}\,\underset{KOH}{\mathop{\xrightarrow{B{{r}_{2}}}}}\,\underset{\text{Ethylamine}}{\mathop{C{{H}_{3}}C{{H}_{2}}N{{H}_{2}}}}\,\]

or \[{{C}_{2}}{{H}_{5}}COOH\underset{{{H}_{2}}S{{O}_{4}}(conc.)}{\mathop{\xrightarrow{{{N}_{3}}H}}}\,{{C}_{2}}{{H}_{5}}N{{H}_{2}}\]

(ii) \[\underset{\text{Propionic acid}}{\mathop{C{{H}_{3}}C{{H}_{2}}COOH}}\,\underset{Ether}{\mathop{\xrightarrow{LiAl{{H}_{4}}}}}\,\underset{n\text{-Propyl alcohol}}{\mathop{C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}OH}}\,\xrightarrow{PB{{r}_{5}}}\underset{\text{Propyl bromide}}{\mathop{C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}Br}}\,\xrightarrow{KCN}\underset{\text{Propyl cyanide}}{\mathop{C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}CN}}\,\]\[\underset{\text{Propyl bromide}}{\mathop{C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}Br}}\,\xrightarrow{KCN}\underset{\text{Propyl cyanide}}{\mathop{C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}CN}}\,\]

\[\underset{\text{o}r\,LiAl{{H}_{4}}}{\mathop{\xrightarrow{Na+{{C}_{2}}{{H}_{5}}OH}}}\,\underset{n\text{-Butylamine}}{\mathop{C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}N{{H}_{2}}}}\,\]

(5) Conversion of ethylene to 1, 4-diaminobutane

\[\underset{\text{Ethylene}}{\mathop{C{{H}_{2}}=C{{H}_{2}}}}\,\underset{CC{{l}_{4}}}{\mathop{\xrightarrow{B{{r}_{2}}}}}\,\underset{\text{Ethylene bromide}}{\mathop{C{{H}_{2}}Br.C{{H}_{2}}Br}}\,\xrightarrow{NaCN}\underset{\text{Ethylene cyanide}}{\mathop{NCC{{H}_{2}}C{{H}_{2}}CN}}\,\xrightarrow{LiAl{{H}_{4}}}\underset{\text{1,4-Diaminobutane}}{\mathop{N{{H}_{2}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}N{{H}_{2}}}}\,\]\[\underset{\text{Ethylene cyanide}}{\mathop{NCC{{H}_{2}}C{{H}_{2}}CN}}\,\xrightarrow{LiAl{{H}_{4}}}\underset{\text{1,4-Diaminobutane}}{\mathop{N{{H}_{2}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}N{{H}_{2}}}}\,\]