i) Reaction of 3-methyl-2-butanol with hydrogen bromide yields 2-bromo-2- methylbutane (major product) and 2-bromo-3-methylbutane (minor product). Draw the mechanism for the above reaction. ii) Name and provide the structure of the major organic product which results when (R)-3, 3-dimethyl-2-butanol is heated in the presence of HBr. iii) When 1-iodo-1-methylcyclohexane is treated with NaOCH2CH3 as the base, the more highly substituted alkene product predominates. When KOC(CH3)3 is used as the base, the less highly substituted alkene predominates. Give the structures of the two products and explain.

i) Reaction of 3-methyl-2-butanol with hydrogen bromide yields 2-bromo-2- methylbutane (major product) and 2-bromo-3-methylbutane (minor product). Draw the mechanism for the above reaction. ii) Name and provide the structure of the major organic product which results when (R)-3, 3-dimethyl-2-butanol is heated in the presence of HBr. iii) When 1-iodo-1-methylcyclohexane is treated with NaOCH2CH3 as the base, the more highly substituted alkene product predominates. When KOC(CH3)3 is used as the base, the less highly substituted alkene predominates. Give the structures of the two products and explain.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 26MP: Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium...

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