Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 3, Problem 40P
Interpretation Introduction

Interpretation: The relative reactivity of hydrogens in 90 % CH3CH2CHBr2 , 8.5 % CH3CHBrCH2Br and 1.5 % BrCH2CH2CH2Br formed should be calculated and compared with similar results of bromination with propane.

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

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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