Predict the products and mechanisms of the following reactions. When more than oneproduct or mechanism is possible, explain which are most likely.(a) 1@bromohexane + sodium ethoxide in ethanol(b) 2@chlorohexane + NaOCH3 in methanol(c) 2-chloro-2-methylbutane + NaOCH2CH3 in ethanol(d) 2-chloro-2-methylbutane heated in ethanol(e) isobutyl iodide + KOH in ethanol>water(f) isobutyl chloride + AgNO3 in ethanol>water

Predict the products and mechanisms of the following reactions. When more than oneproduct or mechanism is possible, explain which are most likely.(a) 1@bromohexane + sodium ethoxide in ethanol(b) 2@chlorohexane + NaOCH3 in methanol(c) 2-chloro-2-methylbutane + NaOCH2CH3 in ethanol(d) 2-chloro-2-methylbutane heated in ethanol(e) isobutyl iodide + KOH in ethanol>water(f) isobutyl chloride + AgNO3 in ethanol>water

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 9.46P: When cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the...

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When cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the substitution product trans-1,4-cyclohexanediol (1). Under the same reaction conditions, trans-4-chlorocyclohexanol gives 3-cyclohexenol (2) and the bicyclic ether (3). (a) Propose a mechanism for formation of product (1), and account for its configuration. (b) Propose a mechanism for formation of product (2). (c) Account for the fact that the bicyclic ether (3) is formed from the trans isomer but not from the cis isomer.
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Predict the products and mechanisms of the following reactions. When more than oneproduct or mechanism is possible, explain which are most likely.(a) 1@bromohexane + sodium ethoxide in ethanol(b) 2@chlorohexane + NaOCH3 in methanol(c) 2-chloro-2-methylbutane + NaOCH2CH3 in ethanol(d) 2-chloro-2-methylbutane heated in ethanol
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Predict the products and mechanisms of the following reactions. When more than oneproduct or mechanism is possible, explain which are most likely.(a) 1@bromohexane + sodium ethoxide in ethanol(b) 2@chlorohexane + NaOCH3 in methanol(c) 2-chloro-2-methylbutane + NaOCH2CH3 in ethanol(d) 2-chloro-2-methylbutane heated in ethanol(e) isobutyl iodide + KOH in ethanol>water(f) isobutyl chloride + AgNO3 in ethanol>water(g) 1@bromo@1@methylcyclopentane + NaOEt in ethanol(h) 1-bromo-1-methylcyclopentane heated in methanol
2,3-Dimethylbutane reacts with bromine in the presence of light to give a mono brominated product. The further reaction gives a good yield of a dibrominated product. Predict the structures of these products, and propose a mechanism for the formation of the mono brominated product.