Q43E - Organic Chemistry (Mcmurry)

Question

How could you convert butanoic acid into the following compounds?
 Write each step showing the reagents needed.
 (a) 1-Butanol (b) 1-Bromobutane (c) Pentanoic acid
(d) 1-Butene (e) Octane

Step-by-Step Solution

Answer

The conversion of butanoic acid into the following compounds can be explained.

Step 1: Conversion of butanoic acid into 1-Butanol

The hydrolysis with acids can happen when treated with LiAlH₄, there is a reduction of butanoic acid to 1-Butanol. The steps involved are,

${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CO}}_2\mathrm{H}\underset{2.{\mathrm{H}}_3{\mathrm{O}}^{+}}{\overset{1{\mathrm{LiAlH}}_4}{\to }}{\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{OH}$

Step 2: Conversion of butanoic acid into 1-Bromobutane

The hydrolysis with acids can happen when treated with LiAlH₄, there is a reduction of butanoic acid to 1-Butanol. Treat it with PBr₃, there is a conversion of alcohol into 1-bromobutane. The steps involved are,

${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CO}}_2\mathrm{H}\underset{2.{\mathrm{H}}_3{\mathrm{O}}^{+}}{\overset{1{\mathrm{LiAlH}}_4}{\to }}{\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{OH}\stackrel{PB{r}_2}{\to }{\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_{2}C{\mathrm{H}}_2\mathrm{Br}$

Step 3: Conversion of butanoic acid into Pentanoic acid

The hydrolysis with acids can happen when treated with LiAlH₄, there is a reduction of butanoic acid to 1-Butanol. Treat it with PBr₃, there is a conversion of alcohol into 1-bromobutane. The butanenitrile hydrolysis with aqueous acids results in pentanoic acid formation.The steps involved are,

${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CO}}_2\mathrm{H}\underset{2.{\mathrm{H}}_3{\mathrm{O}}^{+}}{\overset{1{\mathrm{LiAlH}}_4}{\to }}{\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{OH}\stackrel{PB{r}_2}{\to }{\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_{2}C{\mathrm{H}}_2\mathrm{Br}\underset{2.H_3{O}^{+}}{\overset{1.NaCN}{\to }}{\mathrm{CH}}_3{\mathrm{CH}}_2$

Step 4: Conversion of butanoic acid into 1-Butene

The hydrolysis with acids can happen when treated with LiAlH₄, there is a reduction of butanoic acid to 1-Butanol. Treat it with PBr₃, there is a conversion of alcohol into 1-bromobutane. Treatment of 1-bromobutane with KOH, eliminates HBr to get 1-butene.The steps involved are,

${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CO}}_2\mathrm{H}\underset{2.{\mathrm{H}}_3{\mathrm{O}}^{+}}{\overset{1{\mathrm{LiAlH}}_4}{\to }}{\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{OH}\stackrel{{\mathrm{PBr}}_2}{\to }{\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{Br}\stackrel{\mathrm{alcoholicKOH}}{\to }{\mathrm{CH}}_3{\mathrm{CH}}_2\mathrm{CH}$

Step 5: Conversion of butanoic acid into Octane

The hydrolysis with acids can happen when treated with LiAlH₄, there is a reduction of butanoic acid to 1-Butanol. Treat it with PBr₃, there is a conversion of alcohol into 1-bromobutane. The conversion of 1-bromobutane into lithiumdibutylcopper in addition to octane. The steps involved are,

${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CO}}_2\mathrm{H}\underset{2.{\mathrm{H}}_3{\mathrm{O}}^{+}}{\overset{1{\mathrm{LiAlH}}_4}{\to }}{\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{OH}\stackrel{{\mathrm{PBr}}_2}{\to }{\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{Br}\stackrel{2 \mathrm{Ll}}{\to }2{\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2{{\mathrm{CH}}_2}^{-}{\mathrm{Li}}^{+}$