7th Edition

ISBN: 9780321803221

Author: Paula Y. Bruice

Publisher: Prentice Hall

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Textbook Question

Chapter 17, Problem 93P

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 17, Problem 93P, 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 17, Problem 92P

Chapter 17, Problem 94P

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Chapter 17 Solutions

Organic Chemistry

Ch. 17.1 - Prob. 1P Ch. 17.1 - Give two names for each of the following:Ch. 17.1 - Name the following:Ch. 17.2 - Prob. 4P Ch. 17.4 - What products are formed when the following...Ch. 17.4 - We saw on the previous page that...Ch. 17.4 - a. How many stereoisomers are obtained from the...Ch. 17.4 - Prob. 9P Ch. 17.4 - Write the mechanism for the reaction of acetyl...Ch. 17.4 - Prob. 11P

Ch. 17.4 - Show how the following compounds can be...Ch. 17.5 - Prob. 13P Ch. 17.5 - Prob. 14P Ch. 17.6 - In the mechanism for cyanohydrin formation, why is...Ch. 17.6 - Prob. 16P Ch. 17.6 - Prob. 17P Ch. 17.6 - Show two ways to convert an alkyl halide into a...Ch. 17.7 - Prob. 20P Ch. 17.7 - Prob. 21P Ch. 17.7 - Prob. 22P Ch. 17.7 - Prob. 23P Ch. 17.8 - Prob. 24P Ch. 17.9 - What reducing agents should be used to obtain the...Ch. 17.9 - Prob. 26P Ch. 17.9 - Prob. 27P Ch. 17.10 - Prob. 28P Ch. 17.10 - Prob. 29P Ch. 17.10 - Prob. 30P Ch. 17.10 - The pKa of protonated acetone is about 7.5. and...Ch. 17.10 - Prob. 32P Ch. 17.10 - Prob. 33P Ch. 17.10 - Prob. 34P Ch. 17.10 - Excess ammonia must be used when a primary amine...Ch. 17.10 - The compounds commonly known as amino acids are...Ch. 17.11 - Hydration of an aldehyde is also catalyzed by...Ch. 17.11 - Which ketone forms the most hydrate in an aqueous...Ch. 17.11 - When trichloroacetaldehyde is dissolved in water,...Ch. 17.12 - Which of the following are a. hermiacetals? b....Ch. 17.12 - Prob. 41P Ch. 17.12 - Explain why an acetal can be isolated but most...Ch. 17.13 - Prob. 43P Ch. 17.13 - Prob. 44P Ch. 17.13 - What products would be formed from the proceedings...Ch. 17.13 - a. In a six-step synthesis, what is the yield of...Ch. 17.13 - Show how each of the following compounds could be...Ch. 17.15 - Prob. 48P Ch. 17.17 - Prob. 50P Ch. 17.18 - Prob. 51P Ch. 17.19 - Prob. 52P Ch. 17 - Draw the structure for each of the following: a....Ch. 17 - Prob. 54P Ch. 17 - Prob. 55P Ch. 17 - a. Show the reagents required to form the primary...Ch. 17 - Prob. 57P Ch. 17 - Using cyclohexanone as the starting material,...Ch. 17 - Prob. 59P Ch. 17 - 60. Show how each of the following compounds could...Ch. 17 - Fill in the boxes:Ch. 17 - Prob. 62P Ch. 17 - Identify A through O:Ch. 17 - Prob. 64P Ch. 17 - Prob. 65P Ch. 17 - Prob. 66P Ch. 17 - How many signals would the product of the...Ch. 17 - Prob. 68P Ch. 17 - Prob. 69P Ch. 17 - Prob. 70P Ch. 17 - Prob. 71P Ch. 17 - Prob. 72P Ch. 17 - Prob. 73P Ch. 17 - Prob. 74P Ch. 17 - Prob. 75P Ch. 17 - Prob. 76P Ch. 17 - Prob. 77P Ch. 17 - A compound gives the following IR spectrum. Upon...Ch. 17 - a. Propose a mechanism for the following reaction:...Ch. 17 - Prob. 80P Ch. 17 - Prob. 81P Ch. 17 - Prob. 82P Ch. 17 - Prob. 83P Ch. 17 - Prob. 84P Ch. 17 - In the presence of an acid catalyst, acetaldehyde...Ch. 17 - Prob. 86P Ch. 17 - Prob. 87P Ch. 17 - Prob. 88P Ch. 17 - A compound reacts with methylmagnesium bromide...Ch. 17 - Show how each of the following compounds can be...Ch. 17 - Prob. 91P Ch. 17 - Prob. 92P Ch. 17 - The pKa values of the carboxylic acid groups of...Ch. 17 - The Baylis-Hillman reaction is a DABCO...Ch. 17 - Prob. 95P Ch. 17 - Prob. 96P

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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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