Q45P - Organic Chemistry (Mcmurry)

Question

How could you convert butanenitrile into the following compounds?

Write each step showing the reagents needed.

(a) 1-Butanol 

(b) Butylamine 

(c) 2-Methyl-3-hexanone

Step-by-Step Solution

Answer

The conversion of the butanenitrile into following compounds can be explained.

Step 1: Conversion of Butanenitrile into 1-Butanol

The conversion of butanenitrile into butanoic acid when base can hydrolyse. The treatment of butanoic acid with LiAlH₄ follows the acidification and reduced into 1-butanol. The steps involved are,

$C{H}_{3}C{H}_{2}C{H}_{2}CN\underset{H_{2}O}{\overset{NaOH}{\to }}C{H}_{3}C{H}_{2}C{H}_{2}C{O}_{2}H\underset{2.H_3{O}^{+}}{\overset{1.LiAl{H}_4}{\to }}C{H}_{3}C{H}_{2}C{H}_{2}C{H}_{2}OH$

Step 2: Conversion of Butanenitrile into Butylamine

The treatment of butanenitrile with LiAlH₄ follows the acidification and reduced into butylamine. The steps involved are,

$C{H}_{3}C{H}_{2}C{H}_{2}CN\underset{2.H_3{O}^{+}}{\overset{1.LiAl{H}_4}{\to }}C{H}_{3}C{H}_{2}C{H}_{2}C{H}_{2}N{H}_2$

Step 3: Conversion of Butanenitrile into 2-Methyl-3-hexanone

The treatment of butanenitrile with isopropylmagnesium in addition to Grignard reagent to triple bond. There is a formation of intermediate in hydrolysis using 2-methyl-3-hexanone. The steps involved are,

$C{H}_{3}C{H}_{2}C{H}_{2}CN\underset{2.H_3{O}^{+}}{\overset{1.{\left(C{H}_3\right)}_{2}CHMgBr}{\mathit{\to }}}C{H}_{\mathit{3}}C{H}_{\mathit{2}}C{H}_{\mathit{2}}\stackrel{\stackrel{\mathrm{O}}{\parallel }}{\mathrm{C}}\underset{\underset{C{H}_3}{|}}{\mathrm{C}}HC{H}_3$