Chapter 8, Problem 73PP

(a)

Interpretation Introduction

Interpretation:

Structural formula should be drawn for the molecular formula ${\text{C}}_{\text{5}}{\text{H}}_{\text{10}}$ that gives 2-methylbutane on hydrogenation reaction with 1 mole molecular hydrogen.

Concept introduction:

• Hydrogenation reaction: It is a process of adding hydrogen molecule across the double bond of alkene.  This process follows syn pathway. Hydrogen addition mechanism follows adsorption phenomenon.
• Generally, hydrogenation of alkenes proceeds in presence of transition metal catalysts like $\text{Pt, Pd, and Ni}$ etc.

(b)

Interpretation Introduction

Interpretation:

The compound with no chiral center is obtained when hydroboration-oxidation of compound X has to be identified.

Concept introduction:

Hydroboration:

Hydroboration is the addition of a hydrogen-boron bond to the Carbon-Carbon, Carbon-Nitrogen, and Carbon-Oxygen double bonds and Carbon-Carbon triple bonds.

When alkene undergoes hydroboration using alkyl borane and hydrogen peroxide followed by hydrolysis which yields the alcohol. The formation of alcohol is depends on the less hindered carbon of the double bond.