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 36P
Interpretation Introduction

Interpretation:

The products A, B, C, and D formed from the sequence of steps from the given starting material, are to be determined.

Concept Introduction:

▸ LDA is the lithium disopyramide. It is a strong base.

▸ In SN2 reaction, one bond is broken and one bond is formed. In SN2 reaction, the nucleophile attacks the carbon with less steric hindrance. The SN2 reaction gives inversion. The reaction takes place in the polar aprotic solvent.

▸ Alkylation of the ketone takes place with the help of lithium enolates.

▸ Sodium hydride is used to generate the enolate ions.

▸ In the diels-alder reaction, two sigma bonds are formed from an expansion of the pi bond of the diene and dienophile.

Ketones react with secondary amines in order to form compounds called enamines.

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For each compound below, propose an efficient synthesis using diethyl malonate as a starting material. Provide explanations for each step in the mechanism. (a) (b) `NH2 (c)
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Chapter 18 Solutions

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