8th Edition

ISBN: 9780134042282

Author: Paula Yurkanis Bruice

Publisher: PEARSON

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Textbook Question

Chapter 15, Problem 77P

a. When a carboxylic acid is dissolved in isotopically labeled water (H₂ ¹⁸O) and an acid catalyst is added, the label is incorporated into both oxygens of the acid. Propose a mechanism to account for this.

Chapter 15, Problem 77P, a. When a carboxylic acid is dissolved in isotopically labeled water (H2 18O) and an acid catalyst

b. If a carboxylic acid is dissolved in isotopically labeled methanol (CH₃ ¹⁸OH) and an acid catalyst is added, where will the label reside in the product?
c. If an ester is dissolved in isotopically labeled water (H₂ ¹⁸O) and an acid catalyst is added, where will the label reside in the product?

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 15, Problem 76P

Chapter 15, Problem 78P

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Chapter 15 Solutions

Organic Chemistry (8th Edition)

Ch. 15.1 - The aromas of many flowers and fruits are due to...Ch. 15.1 - Name the following:Ch. 15.1 - Prob. 3P Ch. 15.2 - Which is longer, the carbon-oxygen single bond in...Ch. 15.2 - There are three carbon-oxygen bonds in methyl...Ch. 15.2 - Prob. 6P Ch. 15.4 - a. What is the product of the reaction of acetyl...Ch. 15.4 - What is the product of an acyl substitution...Ch. 15.5 - a. Which compound has the stretching vibration for...Ch. 15.5 - Using the pKa values listed in Table 15.1, predict...

Ch. 15.5 - Is the following statement true or false? If the...Ch. 15.6 - Starting with acetyl chloride, what neutral...Ch. 15.6 - Prob. 13P Ch. 15.7 - Starting with methyl acetate, what neutral...Ch. 15.7 - We saw that it is necessary to use excess amine in...Ch. 15.7 - Prob. 17P Ch. 15.7 - Which ester hydrolyzes more rapidly? a. methyl...Ch. 15.7 - a. state three factors that cause the uncatalyzed...Ch. 15.8 - Prob. 21P Ch. 15.8 - Using the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 23P Ch. 15.8 - Show the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 25P Ch. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.9 - Prob. 28P Ch. 15.9 - Prob. 29P Ch. 15.10 - Show how each of the following esters could he...Ch. 15.10 - Prob. 32P Ch. 15.11 - Prob. 33P Ch. 15.11 - Which of the following reactions leads to the...Ch. 15.12 - Prob. 35P Ch. 15.12 - Prob. 36P Ch. 15.13 - Prob. 37P Ch. 15.14 - Prob. 38P Ch. 15.14 - Prob. 39P Ch. 15.15 - Prob. 40P Ch. 15.15 - Which alkyl halides from the carboxylic acids...Ch. 15.16 - Prob. 43P Ch. 15.16 - Prob. 44P Ch. 15.16 - Prob. 45P Ch. 15.17 - Prob. 46P Ch. 15.18 - How could you synthesize the following compounds...Ch. 15 - Prob. 48P Ch. 15 - Name the following:Ch. 15 - Prob. 50P Ch. 15 - What compound are obtained from the fallowing...Ch. 15 - a. Rank the following esters in order of...Ch. 15 - Because bromocyclohexane is a secondary alkyl...Ch. 15 - a. Which compound would you expect to have a...Ch. 15 - How could you use 1H NMR spectroscopy to...Ch. 15 - Rank the following compounds in order of...Ch. 15 - Prob. 57P Ch. 15 - Prob. 58P Ch. 15 - Prob. 59P Ch. 15 - A compound with molecular formula C5H10O2 gives...Ch. 15 - Prob. 61P Ch. 15 - Prob. 62P Ch. 15 - Prob. 63P Ch. 15 - Prob. 64P Ch. 15 - Prob. 65P Ch. 15 - Prob. 66P Ch. 15 - Two products, A and B, are obtained from the...Ch. 15 - Prob. 68P Ch. 15 - Prob. 69P Ch. 15 - Prob. 70P Ch. 15 - Prob. 71P Ch. 15 - Prob. 72P Ch. 15 - When treated with an equivalent of methanol,...Ch. 15 - a. Identify the two products obtained from the...Ch. 15 - Prob. 75P Ch. 15 - Prob. 76P Ch. 15 - a. When a carboxylic acid is dissolved in...Ch. 15 - Prob. 78P Ch. 15 - Identity the major and minor products of the...Ch. 15 - When a compound with molecular formula C11H14O2...Ch. 15 - Prob. 81P Ch. 15 - Prob. 82P Ch. 15 - Prob. 83P Ch. 15 - The 1H NMR spectra for two esters with molecular...Ch. 15 - Show how the following compounds could be prepared...Ch. 15 - Prob. 86P Ch. 15 - Prob. 87P Ch. 15 - The intermediate shown here is formed during the...Ch. 15 - Prob. 89P Ch. 15 - Propose a mechanism that accounts for the...Ch. 15 - Catalytic antibodies catalyze a reaction by...Ch. 15 - Prob. 92P

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Solution Summary: The author proposes the mechanism for the given reaction. Carboxylic acid shows nucleophilic acyl substitution reaction, which results in increased electrophilicity of the carbonyl carbon

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Chapter 15 Solutions