Given How the phosphorane required can be prepared is to be shown. A mechanism for the hydrolysis step is to be proposed. Concept introduction: Phosphoranes required for Wittig reaction are prepared by the SN 2 reaction of a primary and some secondary alkyl halides withtriphenyl phosphine followed by treatment with bases like butyl lithium in THF. To show: How the phosphorane required for the reaction can be prepared. To propose: A mechanism for the hydrolysis step.

Question

The following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxide

Answer 1

Question

Chapter 19.SE, Problem 39MP

Interpretation Introduction

Interpretation:

Given

How the phosphorane required can be prepared is to be shown. A mechanism for the hydrolysis step is to be proposed.

Concept introduction:

Phosphoranes required for Wittig reaction are prepared by the SN² reaction of a primary and some secondary alkyl halides withtriphenyl phosphine followed by treatment with bases like butyl lithium in THF.

To show:

How the phosphorane required for the reaction can be prepared.

To propose:

A mechanism for the hydrolysis step.

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The following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxide

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