8-7b - Organic Chemistry (Mcmurry)

Question

What products would you expect from oxymercuration-demercuration of the following alkenes?

a) 

b) 

Step-by-Step Solution

Answer

b) The product obtained from oxymercuration-demercuration of alkene is,

Oxymercuration-Demercuration procedure

Oxymercuration in an electrophilic addition reaction in which  to an alkene, when alkene is treated with $\mathrm{Hg}{\left(\mathrm{OAc}\right)}_2$ . This intermediate organomercury compound is further treated with  and the last step involves the demercuration to form an alcohol.

The product obtained from oxymercuration-demercuration of alkene

b) In this alkene, oxymercuration results in the Markovnikov addition of to an alkene. Here, the OH is added to that carbon which is more substituted, and H is added to that carbon which is less substituted.

The product obtained from oxymercuration-demercuration of alkene