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Consider the following two compounds. These compounds are

Chapter 5, Problem 5.48

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QUESTION:

Consider the following two compounds. These compounds are stereoisomers of 1,2,3- trimethylcyclohexane. One of these compounds has three chirality centers, while the other compound has only two chirality centers. Identify which compound has only two chirality centers and explain why

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QUESTION:

Consider the following two compounds. These compounds are stereoisomers of 1,2,3- trimethylcyclohexane. One of these compounds has three chirality centers, while the other compound has only two chirality centers. Identify which compound has only two chirality centers and explain why

ANSWER:

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The central carbon atom has what seem to be two of the same substituent on either side in both compounds. If they are the same substituent, this would make the central carbon achiral, leaving only two chiral centers. This is only possible if the two substituents also have the same chirality.

     

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