Organic Chemistry, 12e Study Guide/Student Solutions Manual

12th Edition

ISBN: 9781119077329

Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder

Publisher: WILEY

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Textbook Question

Chapter 19, Problem 40P

When the aldol reaction of acetaldehyde is carried out in D 2 O , no deuterium is found in the methyl group of unreacted aldehyde. However, in the aldol reaction of acetone, deuterium is incorporated in the methyl group of the unreacted acetone. Explain this difference in behavior.

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

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Chapter 19, Problem 39P

Chapter 19, Problem 41P

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Chapter 19 Solutions

Organic Chemistry, 12e Study Guide/Student Solutions Manual

Ch. 19 - PRACTICE PROBLEM 19.1 (a) Write a mechanism. for...Ch. 19 - Practice Problem 19.2 Since the products obtained...Ch. 19 - Prob. 3PP Ch. 19 - PRACTICE PROBLEM 19.4 Write mechanisms that...Ch. 19 - Prob. 5PP Ch. 19 - Prob. 6PP Ch. 19 - Practice Problem 19.7 The acid-catalyzed aldol...Ch. 19 - Prob. 8PP Ch. 19 - Practice Problem 19.9 (a) Provide a mechanism for...Ch. 19 - Prob. 10PP

Ch. 19 - Practice Problem 19.11 Outlined below is a...Ch. 19 - Prob. 12PP Ch. 19 - Prob. 13PP Ch. 19 - Prob. 14PP Ch. 19 - Practice Problem 19.15 Starting with ketones and...Ch. 19 - Practice Problem 19.16 Assuming that dehydration...Ch. 19 - Practice Problem 19.17 What starting compound...Ch. 19 - Practice Problem 19.18 What experimental...Ch. 19 - Prob. 19PP Ch. 19 - Practice Problem 19.20 When acrolein (propenal)...Ch. 19 - Prob. 21PP Ch. 19 - PRACTICE PROBLEM 19.22 Qutline reasonable...Ch. 19 - Prob. 23P Ch. 19 - Show all steps in the following syntheses. You may...Ch. 19 - Prob. 25P Ch. 19 - Prob. 26P Ch. 19 - Prob. 27P Ch. 19 - 19.28 Show how the diketone at the right could be...Ch. 19 - Prob. 29P Ch. 19 - 19.30 Write a detailed mechanism for the following...Ch. 19 - Prob. 31P Ch. 19 - Prob. 32P Ch. 19 - 19.33 Predict the products from each of the...Ch. 19 - Prob. 34P Ch. 19 - Show how each of the following transformations...Ch. 19 - Prob. 36P Ch. 19 - What reagents would you use to bring about each...Ch. 19 - Prob. 38P Ch. 19 - Prob. 39P Ch. 19 - 19.40 When the aldol reaction of acetaldehyde is...Ch. 19 - Prob. 41P Ch. 19 - Prob. 42P Ch. 19 - 19.43 The following reaction illustrates the...Ch. 19 - What is the structure of the cyclic compound that...Ch. 19 - Prob. 45P Ch. 19 - Prob. 46P Ch. 19 - Prob. 47P Ch. 19 - Predict the products from the following reactions....Ch. 19 - Prob. 49P Ch. 19 - Prob. 50P Ch. 19 - Prob. 51P Ch. 19 - Prob. 52P Ch. 19 - Prob. 53P Ch. 19 - The Perkin condensation is an aldol-type...Ch. 19 - 19.55 (a) Infrared spectroscopy provides an easy...Ch. 19 - Allowing acetone to react with 2 molar equivalents...Ch. 19 - (+) Fenchone is a terpenoid that can be isolated...Ch. 19 - Prob. 58P Ch. 19 - Prob. 59P Ch. 19 - 19.60 Develop a synthesis for the following...Ch. 19 - 19.61 Provide a mechanism for each of the...Ch. 19 - 19.62 (a) Deduce the structure of product A,...Ch. 19 - Prob. 63P Ch. 19 - Prob. 1LGP

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When the aldol reaction of acetaldehyde is carried out in D 2 O , no deuterium is found in the methyl group of unreacted aldehyde . However, in the aldol reaction of acetone, deuterium is incorporated in the methyl group of the unreacted acetone. Explain this difference in behavior.

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