The possible products containing only one bromine has to be predicted. Concept Introduction: Free radical stability: As the number of carbon substituents increases, the stability of the free radical increases. Selectivity determining step: The selectivity determining step is the breakage of the C-H bond by a halogen radical. Only one H at a time is replaced, if allowed to react for a long enough time, all Hydrogen atoms will be replaced with halogens.

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Chapter 12, Problem 12.69CP

a)

Interpretation Introduction

Interpretation:

The possible products containing only one bromine has to be predicted.

Concept Introduction:

Free radical stability: As the number of carbon substituents increases, the stability of the free radical increases.

Selectivity determining step: The selectivity determining step is the breakage of the C-H bond by a halogen radical. Only one H at a time is replaced, if allowed to react for a long enough time, all Hydrogen atoms will be replaced with halogens.

b)

Interpretation Introduction

Interpretation:

The possible products containing two bromines that are not on the same carbon has to be predicted.

Concept Introduction:

Free radical stability: As the number of carbon substituents increases, the stability of the free radical increases.

Selectivity determining step: The selectivity determining step is the breakage of the C-H bond by a halogen radical. Only one hydrogen atom at a time is replaced, if allowed to react for a long enough time, all hydrogen atoms will be replaced with halogens.

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