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There are three diastereomers of 2-bromo-1,3-dimethylcyclohexane. (a) Using the orientation of the chair conformation shown below, draw all three diastereomers of 2-bromo-1,3-dimethyleyclohexane. Follow the numbering given when placing the positions of the two methyl groups and make sure that the bromine leaving group remains in the axial position as shown. 1 2 3 Br Diastereomer 1 Diastereomer 2 Diastereomer 3 (b) Only 2 of these diastereomers undergo an E2 reaction with HO-. Based on the nature of the required transition states for E2 reactions, indicate with an asterisks *, which of the ones you drew in part (a) above undergoes an E2 reaction? (c) The diastereomer that does not undergo an E2 reaction, reacts with HO to form the Sn2 product instead. Draw the structure of this Sn2 product.

There are three diastereomers of 2-bromo-1,3-dimethylcyclohexane. (a) Using the orientation of the chair conformation shown below, draw all three diastereomers of 2-bromo-1,3-dimethyleyclohexane. Follow the numbering given when placing the positions of the two methyl groups and make sure that the bromine leaving group remains in the axial position as shown. 1 2 3 Br Diastereomer 1 Diastereomer 2 Diastereomer 3 (b) Only 2 of these diastereomers undergo an E2 reaction with HO-. Based on the nature of the required transition states for E2 reactions, indicate with an asterisks *, which of the ones you drew in part (a) above undergoes an E2 reaction? (c) The diastereomer that does not undergo an E2 reaction, reacts with HO to form the Sn2 product instead. Draw the structure of this Sn2 product.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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There are three diastereomers of 2-bromo-1,3-dimethylcyclohexane. (a) Using the orientation of the chair conformation shown below, draw all three diastereomers of 2-bromo-1,3-dimethyleyclohexane. Follow the numbering given when placing the positions of the two methyl groups and make sure that the bromine leaving group remains in the axial position as shown. 1 2 3 Br Diastereomer 1 Diastereomer 2 Diastereomer 3 (b) Only 2 of these diastereomers undergo an E2 reaction with HO-. Based on the nature of the required transition states for E2 reactions, indicate with an asterisks *, which of the ones you drew in part (a) above undergoes an E2 reaction? (c) The diastereomer that does not undergo an E2 reaction, reacts with HO to form the SN2 product instead. Draw the structure of this SN2 product.
Transcribed Image Text:There are three diastereomers of 2-bromo-1,3-dimethylcyclohexane. (a) Using the orientation of the chair conformation shown below, draw all three diastereomers of 2-bromo-1,3-dimethyleyclohexane. Follow the numbering given when placing the positions of the two methyl groups and make sure that the bromine leaving group remains in the axial position as shown. 1 2 3 Br Diastereomer 1 Diastereomer 2 Diastereomer 3 (b) Only 2 of these diastereomers undergo an E2 reaction with HO-. Based on the nature of the required transition states for E2 reactions, indicate with an asterisks *, which of the ones you drew in part (a) above undergoes an E2 reaction? (c) The diastereomer that does not undergo an E2 reaction, reacts with HO to form the SN2 product instead. Draw the structure of this SN2 product.
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