8th Edition

ISBN: 9781305580350

Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher: Cengage Learning

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Textbook Question

Chapter 18.8, Problem DQ

The following sequence of steps is used to create the carboxylic acids that can be used as the first reactant, where X can be a wide variety of groups. Answer true or false about each of the following statements.

Chapter 18.8, Problem DQ, The following sequence of steps is used to create the carboxylic acids that can be used as the first

1. Step 1 would best be performed at a pH below the pK_a of ammonium.
2. Step 1 would create an imine that undergoes nucleophilic attack by cyanide in Step 2.
3. The hydrolysis of the nitrile created in Step 2 would be better performed in base rather than the acid shown.
4. Step 4 is a resolution of a racemic mixture that results from Steps 1–3 and does not require a chiral reagent.

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

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Chapter 18 Solutions

Organic Chemistry

Ch. 18.1 - Prob. 18.1P Ch. 18.2 - Prob. 18.2P Ch. 18.4 - Prob. 18.3P Ch. 18.4 - Prob. 18.4P Ch. 18.4 - Synthesis of nitriles by nucleophilic displacement...Ch. 18.5 - Complete the following transesterification...Ch. 18.6 - Complete and balance equations for the following...Ch. 18.8 - Prob. AQ Ch. 18.8 - Several compounds have been found to inhibit...Ch. 18.8 - Prob. CQ

Ch. 18.8 - The following sequence of steps is used to create...Ch. 18.9 - Prob. 18.8P Ch. 18.9 - Prob. 18.9P Ch. 18.10 - Prob. 18.10P Ch. 18.10 - Show how to convert (R)-2-phenylpropanoic acid to...Ch. 18 - Prob. 18.12P Ch. 18 - Write the IUPAC name for each compound. (a)...Ch. 18 - Prob. 18.14P Ch. 18 - Prob. 18.15P Ch. 18 - Propose a structural formula for compound A,...Ch. 18 - Propose a structural formula for compound B,...Ch. 18 - Propose a structural formula for each compound...Ch. 18 - Draw a structural formula for the principal...Ch. 18 - Prob. 18.20P Ch. 18 - Prob. 18.21P Ch. 18 - Prob. 18.22P Ch. 18 - Prob. 18.23P Ch. 18 - Prob. 18.24P Ch. 18 - Show the product expected when the following...Ch. 18 - The reagent diisobutylaluminum hydride (DIBALH)...Ch. 18 - Prob. 18.27P Ch. 18 - Prob. 18.28P Ch. 18 - Prob. 18.29P Ch. 18 - Nicotinic acid, more commonly named niacin, is one...Ch. 18 - Prob. 18.31P Ch. 18 - Prob. 18.32P Ch. 18 - Prob. 18.33P Ch. 18 - Prob. 18.34P Ch. 18 - Prob. 18.35P Ch. 18 - Isoniazid, a drug used to treat tuberculosis, is...Ch. 18 - Prob. 18.37P Ch. 18 - A step in a synthesis of PGE1 (prostaglandin E1,...Ch. 18 - Prob. 18.39P Ch. 18 - Prob. 18.40P Ch. 18 - Show how to synthesize 5-nonanone from...Ch. 18 - Prob. 18.42P Ch. 18 - The following sequence of steps converts...Ch. 18 - Prob. 18.44P Ch. 18 - Prob. 18.45P Ch. 18 - Prob. 18.46P Ch. 18 - Prob. 18.47P Ch. 18 - Following is a retrosynthetic analysis for the...Ch. 18 - Prob. 18.50P Ch. 18 - Given this retrosynthetic analysis, propose a...Ch. 18 - Prob. 18.52P Ch. 18 - Prob. 18.53P Ch. 18 - Prob. 18.54P Ch. 18 - In Problem 7.28, we saw this step in Johnsons...Ch. 18 - Prob. 18.56P Ch. 18 - Prob. 18.57P Ch. 18 - Prob. 18.58P Ch. 18 - Prob. 18.59P Ch. 18 - Prob. 18.60P Ch. 18 - Prob. 18.61P Ch. 18 - Prob. 18.62P Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Minoxidil is a molecule that causes hair growth in...Ch. 18 - Prob. 18.69P Ch. 18 - Prob. 18.70P Ch. 18 - Prob. 18.71P

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Solution Summary: The author explains the reasons for true and false statements. The rate of formation of carboxylic acid from nitrile is very slow.

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