Student's Study Guide and Solutions Manual for Organic Chemistry

8th Edition

ISBN: 9780134066585

Author: Paula Yurkanis Bruice

Publisher: PEARSON

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Textbook Question

Chapter 16, Problem 95P

The pK_a values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98.

a. Which carboxyl group is the stronger acid?
b. The amount of hydrate present in an aqueous solution of oxaloacetic acid depends on the pH of the solution: 95% at pH 0, 81% at pH 1.3, 35% at pH 3.1, 13% at pH 4.7, 6% at pH 6.7, and 6% at pH 12.7. Explain this pH dependence.

Chapter 16, Problem 95P, The pKa values of the carboxylic acid groups of oxaloacetic acid are 2.22 and 3.98. a. Which

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 16, Problem 94P

Chapter 16, Problem 96P

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Chapter 16 Solutions

Student's Study Guide and Solutions Manual for Organic Chemistry

Ch. 16.1 - Give two names for each of the following:Ch. 16.1 - Prob. 2P Ch. 16.1 - Name the following:Ch. 16.2 - Prob. 4P Ch. 16.4 - What products are formed when the following...Ch. 16.4 - We saw on the previous page that...Ch. 16.4 - a. How many stereoisomers are obtained from the...Ch. 16.4 - Prob. 9P Ch. 16.4 - Write the mechanism for the reaction of acetyl...Ch. 16.4 - Prob. 11P

Ch. 16.4 - Show how the following compounds can be...Ch. 16.4 - Prob. 13P Ch. 16.4 - Prob. 14P Ch. 16.4 - In the mechanism for cyanohydrin formation, why is...Ch. 16.4 - Prob. 16P Ch. 16.4 - Prob. 17P Ch. 16.4 - Show two ways to convert an alkyl halide into a...Ch. 16.5 - Prob. 20P Ch. 16.5 - Prob. 21P Ch. 16.5 - Prob. 22P Ch. 16.5 - Prob. 23P Ch. 16.6 - Prob. 24P Ch. 16.7 - What reducing agents should be used to obtain the...Ch. 16.7 - Prob. 26P Ch. 16.8 - Prob. 27P Ch. 16.8 - Prob. 28P Ch. 16.8 - Prob. 29P Ch. 16.8 - The pKa of protonated acetone is about 7.5. and...Ch. 16.8 - Prob. 31P Ch. 16.8 - Prob. 32P Ch. 16.8 - Prob. 33P Ch. 16.8 - Excess ammonia must be used when a primary amine...Ch. 16.8 - The compounds commonly known as amino acids are...Ch. 16.9 - Hydration of an aldehyde is also catalyzed by...Ch. 16.9 - Which ketone forms the most hydrate in an aqueous...Ch. 16.9 - When trichloroacetaldehyde is dissolved in water,...Ch. 16.9 - Which of the following are a. hermiacetals? b....Ch. 16.9 - Prob. 40P Ch. 16.9 - Explain why an acetal can be isolated but most...Ch. 16.10 - Prob. 42P Ch. 16.10 - Prob. 43P Ch. 16.10 - What products would be formed from the proceedings...Ch. 16.10 - a. In a six-step synthesis, what is the yield of...Ch. 16.10 - Show how each of the following compounds could be...Ch. 16.12 - Prob. 47P Ch. 16.13 - Prob. 49P Ch. 16.14 - Prob. 50P Ch. 16.15 - Prob. 51P Ch. 16.16 - Prob. 52P Ch. 16 - Draw the structure for each of the following: a....Ch. 16 - Prob. 54P Ch. 16 - Prob. 55P Ch. 16 - Prob. 56P Ch. 16 - a. Show the reagents required to form the primary...Ch. 16 - Prob. 58P Ch. 16 - Prob. 59P Ch. 16 - Using cyclohexanone as the starting material,...Ch. 16 - Propose a mechanism for each of the following...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Fill in the boxes:Ch. 16 - Prob. 64P Ch. 16 - Identify A through O:Ch. 16 - Prob. 66P Ch. 16 - Prob. 67P Ch. 16 - Prob. 68P Ch. 16 - How many signals would the product of the...Ch. 16 - Prob. 70P Ch. 16 - Prob. 71P Ch. 16 - Prob. 72P Ch. 16 - Prob. 73P Ch. 16 - Prob. 74P Ch. 16 - Prob. 75P Ch. 16 - Prob. 76P Ch. 16 - Prob. 77P Ch. 16 - Prob. 78P Ch. 16 - Draw structure for A-D for each of the following:Ch. 16 - Prob. 80P Ch. 16 - a. Propose a mechanism for the following reaction:...Ch. 16 - Prob. 82P Ch. 16 - A compound gives the following IR spectrum. Upon...Ch. 16 - How can be following compounds be prepared from...Ch. 16 - Prob. 85P Ch. 16 - Prob. 86P Ch. 16 - Prob. 87P Ch. 16 - In the presence of an acid catalyst, acetaldehyde...Ch. 16 - Prob. 89P Ch. 16 - Prob. 90P Ch. 16 - Prob. 91P Ch. 16 - A compound reacts with methylmagnesium bromide...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Prob. 94P Ch. 16 - The pKa values of the carboxylic acid groups of...Ch. 16 - The Baylis-Hillman reaction is a DABCO...Ch. 16 - Prob. 97P Ch. 16 - Prob. 98P

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Solution Summary: The author explains that in oxaloacetic acid which carboxyl group is stronger has to be identified.

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Chapter 16 Solutions