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Organic Chemistry | 9th Edition | ISBN: 9780321971371 | Authors: Leroy G. Wade, Jan W. Simek
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Predict the elimination products of the following reactions, and label the major

Chapter 7, Problem PROBLEM 7-28

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QUESTION:

Predict the elimination products of the following reactions, and label the major products. (a) cis-1-bromo-2-methylcyclohexane + NaOCH3 in CH3OH (b) trans-1-bromo-2-methylcyclohexane + NaOCH3 in CH3OH

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QUESTION:

Predict the elimination products of the following reactions, and label the major products. (a) cis-1-bromo-2-methylcyclohexane + NaOCH3 in CH3OH (b) trans-1-bromo-2-methylcyclohexane + NaOCH3 in CH3OH

ANSWER:

Step 1 of 2

The solvent methanol means the elimination proceeds through  E1. Thus, the stereochemistry of the substrate does not affect the stereochemistry of the product.

Thus, a diastereomer is obtained.

indicates these reactions occur viaEl, therefore stereochemistry of theeliminating halogen and adjacent hydrogen is not an issue. Both reactions yield a mix of diastereomeric alkenes (the E and Z alkene form for both reactions).

                                                       

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