Q10P - Organic Chemistry (Mcmurry)

Question

What alkenes might be used to prepare the following alcohols by hydroboration-oxidation?

Step-by-Step Solution

Answer

Step 1: Introduction

Hydroboration-oxidation is a process that produce alcohols, involving two steps. Anti-Markonikov rule is followed in which hydrogen from ${\text{BH}}_{\text{3}}$  attaches itself to the more substituted carbon and boron attaches to the least substituted carbon in alkene double bond. Boron accepts two electrons from electron rich alkene,  in its empty p orbital. This Anti-Markonokov hydroboration mechanism is stereospecific (syn addition), in which the hydroboration takes place on the same face of the double bond leading to syn product

Step 2: Explanation

In order to find out what alkene might be used to generate, alcohols given in the question, we need to workout in a reverse manner of what we diid in hydroboration-oxidation reaction process. And following this we can get the answer easily.

 

 a)

b) 

c)