Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 21, Problem 21.55SP

(a)

Interpretation Introduction

Interpretation:

The major product of the given reaction is to be stated.

Concept introduction:

The reaction of an ester with excess Grignard reagent followed by hydrolysis converts an ester into tertiary alcohol through tetrahedral intermediate. The Grignard reaction takes place in three steps. The first step is addition of Grignard reagent. The second is elimination of alkoxide followed by formation of ketone. The third step is addition of another Grignard reagent followed by formation of an alkoxide. The fourth step is hydrolysis of an alkoxide to yield tertiary alcohols.

(b)

Interpretation Introduction

Interpretation:

The synthesis of 3-ethylpentan-3-ol with the use of diethyl carbonate and ethyl bromide as organic reagents is to be stated.

Concept introduction:

The reaction of an ester with excess Grignard reagent followed by hydrolysis converts an ester into tertiary alcohol through tetrahedral intermediate. The Grignard reaction takes place in three steps. The first step is addition of Grignard reagent. The second is elimination of alkoxide followed by formation of ketone. The third step is addition of another Grignard reagent followed by formation of an alkoxide. The fourth step is hydrolysis of an alkoxide to yield tertiary alcohols.

(c)

Interpretation Introduction

Interpretation:

The preparation of Lexan with the use of diethyl carbonate instead of phosgene and the preparation of Sevin (an insecticide) with the use of diethyl carbonate instead of methyl isocyanate are to be stated.

Concept introduction:

Diethyl carbonate is an ester (carbonic acid and ethanol). It is a liquid reagent that is easy to handle. However, phosgene is a corrosive and highly toxic. Diethyl carbonate successfully replaces phosgene in the synthesis of Lexan and Sevin.

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Chapter 21 Solutions

Organic Chemistry (9th Edition)

Ch. 21.7C - Prob. 21.20PCh. 21.7C - Prob. 21.21PCh. 21.7D - Prob. 21.22PCh. 21.7D - The mechanism for acidic hydrolysis of a nitrile...Ch. 21.8A - Prob. 21.24PCh. 21.8C - Prob. 21.25PCh. 21.9 - Prob. 21.26PCh. 21.9 - Prob. 21.27PCh. 21.9 - Prob. 21.28PCh. 21.10 - Draw a mechanism for the acylation of anisole by...Ch. 21.10 - Prob. 21.30PCh. 21.11 - Prob. 21.31PCh. 21.11 - Prob. 21.32PCh. 21.12 - Problem 21-33 Propose a mechanism for the...Ch. 21.12 - Suggest the most appropriate reagent for each...Ch. 21.12 - Show how you would synthesize each compound,...Ch. 21.13 - Prob. 21.36PCh. 21.13 - Prob. 21.37PCh. 21.14 - Prob. 21.38PCh. 21.14 - Prob. 21.39PCh. 21.16 - Prob. 21.40PCh. 21.16 - Prob. 21.41PCh. 21 - Prob. 21.42SPCh. 21 - Give appropriate names for the following...Ch. 21 - Predict the major products formed when benzoyl...Ch. 21 - Predict the products of the following reactions....Ch. 21 - Prob. 21.46SPCh. 21 - Prob. 21.47SPCh. 21 - Prob. 21.48SPCh. 21 - Propose mechanisms for the following reactions.Ch. 21 - Prob. 21.51SPCh. 21 - An ether extraction of nutmeg gives large...Ch. 21 - Prob. 21.53SPCh. 21 - Show how you would accomplish the following...Ch. 21 - Prob. 21.55SPCh. 21 - Prob. 21.56SPCh. 21 - Prob. 21.57SPCh. 21 - Prob. 21.58SPCh. 21 - Prob. 21.59SPCh. 21 - Explain this curious result. What does this...Ch. 21 - Prob. 21.61SPCh. 21 - Prob. 21.62SPCh. 21 - Prob. 21.63SPCh. 21 - A chemist was called to an abandoned aspirin...Ch. 21 - Prob. 21.67SPCh. 21 - The IR spectrum, 13ONTVTR spectrum, and 1HNMR...Ch. 21 - Prob. 21.69SPCh. 21 - Prob. 21.70SPCh. 21 - Prob. 21.71SP
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