Poor selectivity in the formation of the brominated products when equimolar mixture of Br 2 and Cl 2 compared to the case when Br 2 alone is taken should be explained. Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism. In general, tertiary 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 C – H bond cleavage via hyperconjugation. The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

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Chapter 3, Problem 38P

Interpretation Introduction

Interpretation: Poor selectivity in the formation of the brominated products when equimolar mixture of Br2 and Cl2 compared to the case when Br2 alone is taken should be explained.

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

In general, tertiary 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 C – H bond cleavage via hyperconjugation.

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

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