Q49P - Organic Chemistry (Mcmurry)

Question

How would you carry out the following transformations?

Step-by-Step Solution

Answer

Methylidenecyclohexane can be transformed into 2-cyclohexylethanoic acid through the steps are

Methylidenecyclohexane can be transformed into 1-methylcyclohexanecarboxylic acid through the steps are

Step 1: Definition of transformations

The conversion of a substrate into a particular product, irrespective of reagents or mechanisms involved is defined as transformations.

Step 2: Explanations

Conversion of methylidenecyclohexane to 2-cyclohexylethanoic acid

Methylidenecyclohexane is subjected to hydroboration by treating it with $B{H}_3$ in THF followed by oxidation with $H_2{O}_2\mathit{,}\mathit{ }O{H}^{\mathit{-}}$. Addition of water to the double bond takes place following anti-Markovnikov regiochemistry to yield cyclohexylmethanol. Treatment of the alcohol with $PB{r}_3$converts it into bromomethylcyclohexane. When treated with NaCN, the bromide is converted into cyanomethylcyclohexane which upon hydrolysis with aqueous acids yields 2-cyclohexylethanoic acid.

Conversion of methylidenecyclohexane to 2-cyclohexylethanoic acid

Methylidenecyclohexane is treated with HBr, hen addition takes place to yield 1-methyl-1-bromocyclohexane. Treatment with Mg in ether converts the bromide to 1-methylcyclohexylmagnesium bromide. The Grignard when treated $C{O}_2$with followed by hydrolysis with aqueous acid produces 2-cyclohexylethanoic acid.

Methylidenecyclohexane can be transformed into 2-cyclohexylethanoic acid through the steps are

Methylidenecyclohexane can be transformed into 1-methylcyclohexanecarboxylic acid through the steps are