Chapter 3.7, Problem 3.9TIY

Interpretation Introduction

Interpretation: The products and ratios obtained after monochlorination of $\text{3-methylpentane}$ at $25°\text{C}$ should be written.

Concept introduction: The chlorination performed with ultraviolet light proceeds via radical chain mechanism.

Tertiary $\text{C – H}$ bonds react in halogenations more readily than secondary those in turn are faster to react than primary. This can be attributed to stability of radical formed upon $\text{C – H}$ bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of $\text{σ}$ electrons into the partly vacant $p$ orbital lobes of radical carbon. More will be number of $\text{σ}$ orbital capable of donation of electrons more is the stabilization.