Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 18, Problem 23P
Interpretation Introduction

Interpretation:

The structural formula of the product formed in each of the given reactions is to be determined.

Concept Introduction:

▸ The βdicarbonyl compound can be converted into enolate ions in the presence of sodium ethoxide.

▸ Alkylation of the βdicarbonyl compound is a SN2 reaction.

▸ Decarboxylation of βketoacid takes place in the presence of heat.

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(a) (b) (c) Suggest a synthesis of the following alkene (A) using a Wittig reaction strategy. Draw the starting material(s), key reagent and a full reaction mechanism including an explanation of the observed geometry. Which of the following (B) and (C) will favour the enol form? Briefly explain your reasoning. Predict the product(s) and provide a mechanism for each of the following transformations: (i) (ii) OMe OMe Base OEt NaOEt
Suggest the most appropriate method for each of the following laboratory syntheses.(a) cyclopentanol ¡ cyclopentanone
Draw a structural formula for the alcohol formed by treating each alkene with borane in tetrahydrofuran (THF) followed by hydrogen peroxide in aqueous sodium hydroxide, and specify stereochemistry where appropriate. (a) (d) (b) (e) (c)

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Organic Chemistry

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