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 3.1, Problem 3.3E

(a)

Interpretation Introduction

Interpretation: The C–C bond that has greater chances of cleavage out of ethane and 2,2-dimethylpropane should be identified.

Concept introduction: At extremely elevated temperature, the C–C bond and C–H undergoes homolytic cleavage. This process generates radicals. Greater will be stability of radicals generated more will be chances of cleavage of the particular bond. Bond dissociation value provides concrete evidence for the stability of radicals. If the energy is low that means stable radicals can be generated by very little energy and vive-versa.

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 to the radical carbon more is the stabilization. On the basis of this tertiary C–H bonds react 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.

(b)

Interpretation Introduction

Interpretation: The preferred product formed from attack of HO radical on 2-dimethylpropane should be written and explained.

Concept introduction: After the homolytic cleavage radicals may recombine with one another and result in variety of alkanes. For example, in pyrolysis of hexane occurs via homolytic fission of either C1–C2 or C2–C3 or C3–C4 . The radicals generated undergo combinations as illustrated below:

  Organic Chemistry: Structure and Function, Chapter 3.1, Problem 3.3E

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