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1. When cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the substitution product trans-1,4-cyclohexanediol (a). Under the same reaction conditions, trans-4-chlorocyclohexanol gives 3-cyclohexenol (b) and the bicyclic ether (c). NaOH ELOH HO HO" NaOH EIOH HO HO HO (a) (b) (c) (a) Propose a mechanism for formation of product (a), and account for its configuration. (b) Propose a mechanism for formation of product (b). (c) Account for the fact that the bicyclic ether (c) is formed from the trans isomer but not from the cis isomer.

1. When cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the substitution product trans-1,4-cyclohexanediol (a). Under the same reaction conditions, trans-4-chlorocyclohexanol gives 3-cyclohexenol (b) and the bicyclic ether (c). NaOH ELOH HO HO" NaOH EIOH HO HO HO (a) (b) (c) (a) Propose a mechanism for formation of product (a), and account for its configuration. (b) Propose a mechanism for formation of product (b). (c) Account for the fact that the bicyclic ether (c) is formed from the trans isomer but not from the cis isomer.

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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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1. When cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the substitution product trans-1,4-cyclohexanediol (a). Under the same reaction conditions, trans-4-chlorocyclohexanol gives 3-cyclohexenol (b) and the bicyclic ether (c). OH CI NaOH ELOH NaOH EIOH HO HO HO HO (a) (b) (c) (a) Propose a mechanism for formation of product (a), and account for its configuration. (b) Propose a mechanism for formation of product (b). (c) Account for the fact that the bicyclic ether (c) is formed from the trans isomer but not from the cis isomer.
Transcribed Image Text:1. When cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the substitution product trans-1,4-cyclohexanediol (a). Under the same reaction conditions, trans-4-chlorocyclohexanol gives 3-cyclohexenol (b) and the bicyclic ether (c). OH CI NaOH ELOH NaOH EIOH HO HO HO HO (a) (b) (c) (a) Propose a mechanism for formation of product (a), and account for its configuration. (b) Propose a mechanism for formation of product (b). (c) Account for the fact that the bicyclic ether (c) is formed from the trans isomer but not from the cis isomer.
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