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Consider the structure of the following compound: (a) When

Chapter 11, Problem 11.41

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QUESTION:

Consider the structure of the following compound:

(a) When this compound is treated with bromine under conditions that favor monobromination, two stereoisomeric products are obtained. Draw them and identify whether they are enantiomers or diastereomers.

(b) When this compound is treated with bromine under conditions that favor dibromination, three stereoisomeric products are obtained. Draw them and explain why there are only three products and not four.

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QUESTION:

Consider the structure of the following compound:

(a) When this compound is treated with bromine under conditions that favor monobromination, two stereoisomeric products are obtained. Draw them and identify whether they are enantiomers or diastereomers.

(b) When this compound is treated with bromine under conditions that favor dibromination, three stereoisomeric products are obtained. Draw them and explain why there are only three products and not four.

ANSWER:

Step 1 of 5

The bromination of substituted cyclohexane follows a radical pathway. The stable product formed depends on the intermediate radical’s stability.

The radical stability follows the order \(1^{0}<2^{0}<3^{0}\).

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