Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
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Chapter 15.8, Problem 23P

(a)

Interpretation Introduction

Interpretation:

To predict the product of acid-catalyzed hydrolysis of given esters.

Concept introduction:

An acid-catalyzed hydrolysis of the ester is a much faster reaction as compared to uncatalyzed hydrolysis of the ester. The addition of acid protonation of the oxygen atom of the carbonyl group and as it is a fact that an oxygen atom with positive charge has more electron withdrawing tendency than neutral atom. The more withdrawal of electron density decreases the electron density from the carbonyl carbon and make it more susceptible for the attack of the nucleophile. The acid catalyzed reaction mechanism is written as,

Organic Chemistry (8th Edition), Chapter 15.8, Problem 23P , additional homework tip  1

Therefore, products obtained by the acid catalyzed ester hydrolysis are the carboxylic acid and an alcohol by which ester was formed.

(b)

Interpretation Introduction

Interpretation:

To predict the product of acid-catalyzed hydrolysis of given esters.

Concept introduction: An acid-catalyzed hydrolysis of the ester is a much faster reaction as compared to uncatalyzed hydrolysis of the ester. The addition of acid protonation of the oxygen atom of the carbonyl group and as it is a fact that an oxygen atom with positive charge has more electron withdrawing tendency than neutral atom. The more withdrawal of electron density decreases the electron density from the carbonyl carbon and make it more susceptible for the attack of the nucleophile. The acid catalyzed reaction mechanism is written as,

Organic Chemistry (8th Edition), Chapter 15.8, Problem 23P , additional homework tip  2

Therefore, products obtained by the acid catalyzed ester hydrolysis are the carboxylic acid and an alcohol by which ester was formed.

(c)

Interpretation Introduction

Interpretation:

To predict the product of acid-catalyzed hydrolysis of given esters.

Concept introduction:

An acid-catalyzed hydrolysis of the ester is a much faster reaction as compared to uncatalyzed hydrolysis of the ester. The addition of acid protonation of the oxygen atom of the carbonyl group and as it is a fact that an oxygen atom with positive charge has more electron withdrawing tendency than neutral atom. The more withdrawal of electron density decreases the electron density from the carbonyl carbon and make it more susceptible for the attack of the nucleophile. The acid catalyzed reaction mechanism is written as,

Organic Chemistry (8th Edition), Chapter 15.8, Problem 23P , additional homework tip  3

Therefore, products obtained by the acid catalyzed ester hydrolysis are the carboxylic acid and an alcohol by which ester was formed.

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Chapter 15 Solutions

Organic Chemistry (8th Edition)

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