Question

Which of the following reaction can not produce $1^{\circ }$ amine as major product?

• A. $H_{3}C-C{H}_2-C\equiv N\underset{\left(\text{complete hydrolysis}\right)}{\overset{H^{+}/H_{2}O}{\to }}$
• B. $H_{3}C-C{H}_2-\stackrel{\stackrel{O}{||}}{C}-OH\stackrel{H{N}_3/H^{+}}{\to }$
• C. $\text{Phthalimide}\underset{ii.H_{3}CC{H}_{2}C{H}_2-I}{\overset{i.O{H}^{-}}{\to }}\stackrel{O{H}^{-}/H_{2}O}{\to }$
• D. $C{H}_3-C{H}_2-Br+N{H}_3\left(\text{excess}\right)\to$

Answer 1

The correct option is A $H_{3}C-C{H}_2-C\equiv N\underset{\left(\text{complete hydrolysis}\right)}{\overset{H^{+}/H_{2}O}{\to }}$

$a).H_{3}C-C{H}_2-C\equiv N\underset{\left(\text{complete hydrolysis}\right)}{\overset{H^{+}/H_{2}O}{\to }}{H}_{3}C-C{H}_2-C{H}_2-COOH$

$b).\text{Schmidt Reaction}{H}_{3}C-C{H}_2-\underset{\underset{O}{||}}{C}-OH\stackrel{N_{3}H/H^{+}}{\to }{H}_{3}C-C{H}_2-N{H}_2$

$c).\text{Gabriel Phthalimide Reaction}\text{Phthalimide}\underset{ii.H_{3}CC{H}_{2}C{H}_2-I}{\overset{i.O{H}^{-}}{\to }}\text{N-propylphthalimide}\stackrel{O{H}^{-}/H_{2}O}{\to }{H}_{3}CC{H}_{2}C{H}_2-N{H}_2$

$d).C{H}_{3}C{H}_2-Br+N{H}_3\text{(excess)}⟶Et-N{H}_2$