Can you please help me with the attached question? Thank you. 1. When cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, itgives mainly the substitution product trans-1,4-cyclohexanediol (a). Under thesame reaction conditions, trans-4-chlorocyclohexanol gives 3-cyclohexenol (b)and the bicyclic ether (c).OHCINaOHELOHNaOHEIOHHOHOHOHO(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 notfrom the cis isomer.

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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.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.39P: Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment with sodium...

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