The structure and stereochemistry of the alcohol that would result if 1, 2-epoxycyclohexane was reduced with Lithium aluminium deuteride are to be shown. Concept introduction: The nucleophilic attack of the deuderide ion on the epoxide will yield an alcohol. The attack takes places by S N 2 like backside attack. When both epoxide carbons are either primary or secondary the nucleophilic attack mainly occurs at the less highly substituted side. When one of the epoxide carbons is tertiary, the nucleophilic attack mainly occurs at the more highly substituted side. To give: The structure and stereochemistry of the alcohol that would result if 1, 2-epoxycyclohexane was reduced with Lithium aluminium deuteride.

Question

When 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1- butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for 70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium propoxide were the base? base Br A. Less than 45% B. C. 45% Between 45% and 70% D. More than 70%

Answer 1

Question

Chapter 18.SE, Problem 52AP

Interpretation Introduction

Interpretation:

The structure and stereochemistry of the alcohol that would result if 1, 2-epoxycyclohexane was reduced with Lithium aluminium deuteride are to be shown.

Concept introduction:

The nucleophilic attack of the deuderide ion on the epoxide will yield an alcohol. The attack takes places by S_N² like backside attack. When both epoxide carbons are either primary or secondary the nucleophilic attack mainly occurs at the less highly substituted side. When one of the epoxide carbons is tertiary, the nucleophilic attack mainly occurs at the more highly substituted side.

To give:

The structure and stereochemistry of the alcohol that would result if 1, 2-epoxycyclohexane was reduced with Lithium aluminium deuteride.

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