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There are two stereoisomers of

Chapter 8, Problem 8.52

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QUESTION:

There are two stereoisomers of 1-tert-butyl-4-chloro-cyclohexane. One of these isomers reacts with sodium ethoxide in an E2 reaction that is 500 times faster than the reaction of the other isomer. Identify the isomer that reacts faster and explain the difference in rate for these two isomers

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QUESTION:

There are two stereoisomers of 1-tert-butyl-4-chloro-cyclohexane. One of these isomers reacts with sodium ethoxide in an E2 reaction that is 500 times faster than the reaction of the other isomer. Identify the isomer that reacts faster and explain the difference in rate for these two isomers

ANSWER:

Step 1 of 2

For an E2 reaction to occur on a cyclohexane molecule, the H atom and leaving group (LG) must be in anti, axial positions. Below are the two stereoisomers of 1-tert-butyl-4-chlorocyclohexane.

     

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