8-8-b - Organic Chemistry (Mcmurry)

Question

From what alkenes might the following alcohols have been prepared?

b) 

Step-by-Step Solution

Answer

b) The alkene needed to produce given alcohol is,

Conversion of alkene to alcohol

When alkenes undergo oxymercuration-demercuration, it results in the formation of alcohol products. It occurs in two steps, the first step is the treatment of alkene with $\mathrm{Hg}{\left(\mathrm{AOc}\right)}_2$ , and the second step is the reduction with NaBH₄.

Preparation of alcohol from alkene

b) The given alcohol is prepared by using oxymercuration-demercuration reaction. When vinylcyclohexane is treated with  $\mathrm{Hg}{\left(\mathrm{AOc}\right)}_2$and in the second step, the product is treated with NaBH₄. The OH is added to that carbon which is highly substituted.

                    Formation of alcohol from alkene