Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 8, Problem 8.21P

(a)

Interpretation Introduction

Interpretation:

A second chain propagation step in the given reaction has to be proposed.

Concept introduction:

Halogenation of alkanes: The replacement of one or more hydrogen atoms by halogen. When alkanes is heated or irradiated with the light of specific wavelength, the alkyl halide are formed by radical chain reaction.

Radical chain reaction:

Initiation reaction: Organic Chemistry, Chapter 8, Problem 8.21P , additional homework tip  1

Chain propagation: Organic Chemistry, Chapter 8, Problem 8.21P , additional homework tip  2

Chain termination:

Organic Chemistry, Chapter 8, Problem 8.21P , additional homework tip  3

(b)

Interpretation Introduction

Interpretation:

Heat of the reaction, ΔH0 for each propagation step has to be calculated.

Concept introduction:

Halogenation of alkanes: The replacement of one or more hydrogen atoms by halogen. When alkanes is heated or irradiated with the light of specific wavelength, the alkyl halide are formed by radical chain reaction.

Radical chain reaction:

Initiation reaction: Organic Chemistry, Chapter 8, Problem 8.21P , additional homework tip  4

Chain propagation: Organic Chemistry, Chapter 8, Problem 8.21P , additional homework tip  5

Chain termination:

Organic Chemistry, Chapter 8, Problem 8.21P , additional homework tip  6

Bond dissociation energy is a measure of bond strength in a chemical bond.

It is a change in enthalpy of a homolysis reaction at absolute zero where a molecule is broken down into two free radicals.

ΔH0=BDE(broken)BDE(formed)

(c)

Interpretation Introduction

Interpretation:

The energies and relative rates of the set chain propagation steps in section 8.5B with given reaction has to be compared.

Concept introduction:

Halogenation of alkanes: The replacement of one or more hydrogen atoms by halogen. When alkanes is heated or irradiated with the light of specific wavelength, the alkyl halide are formed by radical chain reaction.

Radical chain reaction:

Initiation reaction: Organic Chemistry, Chapter 8, Problem 8.21P , additional homework tip  7

Chain propagation: Organic Chemistry, Chapter 8, Problem 8.21P , additional homework tip  8

Chain termination:

Organic Chemistry, Chapter 8, Problem 8.21P , additional homework tip  9

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Compounds containing a phenol group may work as ANTIOXIDANTS to prevent free radical damage. This is accomplished when a free radical (or UV light) encounters a phenol group, turning the phenol group into a radical. However, contrary to typical radical behavior, the structure of the phenol radical can neutralize (or quench) the unpaired electron. Specifically, the phenol structure neutralizes (or quenches) the unpaired radical electron by doing the following: taking the electron and The correct name (or abbreviation) of an example compound (discussed in the lecture videos) containing a phenol group with antioxidant properties is:
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Describe the three stages (initiation, propagation and termination) of radical reactions. Provide also a sample diagram (illustration) for these reactions.
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