Connect Access Card Two Year for Organic Chemistry
Connect Access Card Two Year for Organic Chemistry
10th Edition
ISBN: 9781259636868
Author: Francis Carey
Publisher: McGraw-Hill Education
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Chapter 21, Problem 31P
Interpretation Introduction

Interpretation:

The structural formula for the enol form of diethyl malonate has to be drawn, the structural formulas for three enols of ethyl acetoacetate have to be drawn, among them, the most and least stable isomer has to be identified and the products of the reaction of bromine with both diethyl malonate and ethyl acetoacetate are to be stated.

Concept introduction:

Enol refers to an intermediate structure that consists of an alkene group attached with a hydroxyl group at one end of its double bond.

The percentage of enol in keto-enol tautomerism depends upon the stability of enol formed.

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Each of the following reactions has been described in the chemical literature and involves an organic reactant somewhat more complex than those we have encountered so far. Nevertheless, on the basis of the topics covered in this chapter, you should be able to write the structure of the principal organic product of each reaction.
(a) What reagents would be used for the conversion of alkene A into the target? (b) What reaction is involved in the conversion of alcohol B into alkene A? Suggest a reagent that might affect this transformation. (c) Give a retrosynthetic analysis showing the disconnection of B, the synthons produced that lead to the synthetic equivalents given (draw their structures).
A hydrocarbon (X), with the molecular formula: C8H14 is reduced in presence of sodium and liquid ammonia to give the only product (Y) with the molecular formula: C8H16. Compounds X and Y both resulting 2,5-dimethylhexane when treated with hydrogen and platinum catalyst (H2/Pt). As a result of the oxidative cleavage of compound Y (by using KMnO4 / H2SO4), a single carboxylic acid derivative with C4H8O2 molecular formula is formed. Again, as a result of the reaction of  Y with perbenzoic acid, the chiral compound C8H14O is observed, but the reaction of compound Y with bromine gives the achiral C8H14Br2 as the product.

Chapter 21 Solutions

Connect Access Card Two Year for Organic Chemistry

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