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.
Chapter18: Ethers And Epoxides; Thiols And Sulfides
Section18.SE: Something Extra
Problem 36MP: Aldehydes and ketones undergo acid-catalyzed reaction with alcohols to yield hemiacetals, compounds...
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