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 16P

(a)

Interpretation Introduction

Interpretation: Nature of below alkyl radical along with names and most stable radical should be described by orbital description.

  Organic Chemistry: Structure and Function, Chapter 3, Problem 16P , additional homework tip  1

Concept introduction: The carbon radical linked to one alkyl/carbon while other two H are termed primary alkyl radical.

The carbon radical linked to two alkyl/carbon atoms and one H is termed secondary alkyl radical. The carbon radical linked to three alkyl groups/carbons and no H is termed tertiary alkyl radical.

The various kinds of alkyl radicals are indicated below:

  Organic Chemistry: Structure and Function, Chapter 3, Problem 16P , additional homework tip  2

The tertiary radicals are most stable followed by secondary and least stable is primary methyl radical. This is because there is maximum stabilization through delocalization 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: Nature of below alkyl radical along with names and most stable radical should be described by orbital description.

  Organic Chemistry: Structure and Function, Chapter 3, Problem 16P , additional homework tip  3

Concept introduction: The carbon radical linked to one alkyl/carbon while other two H are termed primary alkyl radical.

The carbon radical linked to two alkyl/carbon atoms and one H is termed secondary alkyl radical. The carbon radical linked to three alkyl groups/carbons and no H is termed tertiary alkyl radical.

The various kinds of alkyl radicals are indicated below:

  Organic Chemistry: Structure and Function, Chapter 3, Problem 16P , additional homework tip  4

The tertiary radicals are most stable followed by secondary and least stable is primary methyl radical. This is because there is maximum stabilization through delocalization 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.

(c)

Interpretation Introduction

Interpretation: Nature of below alkyl radical along with names and most stable radical should be described by orbital description.

  Organic Chemistry: Structure and Function, Chapter 3, Problem 16P , additional homework tip  5

Concept introduction: The carbon radical linked to one alkyl/carbon while other two H are termed primary alkyl radical.

The carbon radical linked to two alkyl/carbon atoms and one H is termed secondary alkyl radical. The carbon radical linked to three alkyl groups/carbons and no H is termed tertiary alkyl radical.

The various kinds of alkyl radicals are indicated below:

  Organic Chemistry: Structure and Function, Chapter 3, Problem 16P , additional homework tip  6

The tertiary radicals are most stable followed by secondary and least stable is primary methyl radical. This is because there is maximum stabilization through delocalization via hyper conjugation. 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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Select all statements that are true  regarding tertiary radicals - Tertiary radicals are more stable than primary radicals due to increased hyperconjugation from attached alkyl groups.  - The CH bond that leads to a tertiary radical via homolysis has a higher bond dissociation energy that the CH bond leading to a primary radical - Tertiary radical hybridization geometry is best described as sp2 hybridization rather than sp3 hybridization - Radical chlorination reactions are more regioselective than radical bromination reactions when a tertiary radical can form.
Please draw the line structures of all of the C8H17+ carbocations that have the carbon-skeleton below. And circle the most stable carbocation of those drawn.
Define the Mechanism of the Radical Addition of HBr to an Alkene ?
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