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Organic Chemistry | 9th Edition | ISBN: 9780321971371 | Authors: Leroy G. Wade, Jan W. Simek
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In the presence of a small amount of bromine, the following light-promoted reaction has

Chapter 4, Problem 4-46

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QUESTION:

In the presence of a small amount of bromine, the following light-promoted reaction has been observed. hv H3C CH3 H3C CH3 CH3 Br H3C Br H Br + 2 + + HBr (a) Write a mechanism for this reaction. Your mechanism should explain how both products are formed. (Hint: Notice which H atom has been lost in both products.) (b) Explain why only this one type of hydrogen atom has been replaced, in preference to any of the other hydrogen atoms in the starting material.

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QUESTION:

In the presence of a small amount of bromine, the following light-promoted reaction has been observed. hv H3C CH3 H3C CH3 CH3 Br H3C Br H Br + 2 + + HBr (a) Write a mechanism for this reaction. Your mechanism should explain how both products are formed. (Hint: Notice which H atom has been lost in both products.) (b) Explain why only this one type of hydrogen atom has been replaced, in preference to any of the other hydrogen atoms in the starting material.

ANSWER:

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(a) In the presence of light photochemical reactions can be promoted. Bromine undergoes free radical dissociation. The mechanism of the reaction is as described below:

During the reaction, the H is abstracted selectively (faster than any other type in the molecule), forming an intermediate represented by two non-equivalent resonance forms.

The partial radical character on two different carbons of the allylic radical leads to two different products.

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