Q8- 24E - Organic Chemistry (Mcmurry)

Question

The following alkene undergoes hydroboration–oxidation to yield a single product rather than a mixture. Explain the result, and draw the product showing its stereochemistry.

Step-by-Step Solution

Answer

BH unit may attack to double bond either above or below the plane but in which BH attacks only attacks sterically hindrance side so only one product is possible.

Step1: Hydroboration–oxidation reaction

An alkene can become alcohol through a two-step hydration reaction called the hydroboration-oxidation reaction. In the process, the double bond is replaced by the simultaneous addition of hydrogen and a hydroxyl group.

Step2:Explain the result, and draw the product

BH unit may attack to double bond either above or below the plane but in which BH attacks only attacks sterically hindrance side so only one product is possible.