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 27P

(a)

Interpretation Introduction

Interpretation: The isomeric products obtained after monobromination of propane should be drawn.

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.

(b)

Interpretation Introduction

Interpretation: The approximate ratio of products obtained, major product of monobromination and whether the selectivity exhibited by bromine is sufficient enough for formation of isomeric products in good yields should be drawn.

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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