Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 16.10, Problem 27P

(a)

Interpretation Introduction

Interpretation:

To predict the products of the following transesterification reaction.

(a) ethyl benzoate + excess isopropanol + HCl

Concept introduction:

Transesterification is the process of formation of a new ester molecule from the reaction of alcohol and an ester. This is like hydrolysis of ester but here nucleophile is alcohol molecule instead of H2O. As alkoxide groups have same basicity, therefore, an excess amount of alcohol is used. The addition of an acid also increases the rate of reaction by protonating the carbonyl oxygen atom. A general transesterification is  written as,

Organic Chemistry, Chapter 16.10, Problem 27P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

To predict the products of the following transesterification reaction.

(b) phenyl acetate + excess ethanol + HCl

Concept introduction:

Transesterification is the process of formation of a new ester molecule from the reaction of alcohol and an ester. This is like hydrolysis of ester but here nucleophile is alcohol molecule instead of H2O. As alkoxide groups have same basicity, therefore, an excess amount of alcohol is used. The addition of an acid also increases the rate of reaction by protonating the carbonyl oxygen atom. A general transesterification is  written as,

Organic Chemistry, Chapter 16.10, Problem 27P , additional homework tip  2

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Chapter 16 Solutions

Organic Chemistry

Ch. 16.5 - a. What is the product of the reaction of acetyl...Ch. 16.6 - a. Which compound has the stretching vibration for...Ch. 16.6 - Using the pKa values listed in Table 15.1, predict...Ch. 16.6 - Is the following statement true or false? If the...Ch. 16.7 - What is the product of an acyl substitution...Ch. 16.8 - PROBLEM 16 Starting with acetyl chloride, what...Ch. 16.8 - Prob. 18PCh. 16.9 - We saw that it is necessary to use excess amine in...Ch. 16.9 - Prob. 20PCh. 16.9 - a. state three factors that cause the uncatalyzed...Ch. 16.10 - Prob. 23PCh. 16.10 - Using the mechanism for the acid-catalyzed...Ch. 16.10 - Prob. 25PCh. 16.10 - Prob. 27PCh. 16.10 - Write the mechanism for the acid-catalyzed...Ch. 16.10 - Write the mechanism for the acid-catalyzed...Ch. 16.11 - Prob. 30PCh. 16.12 - Prob. 31PCh. 16.12 - Prob. 32PCh. 16.13 - Prob. 34PCh. 16.13 - Which has a higher melting point, glyceryl...Ch. 16.13 - Draw the structure of an optically inactive fat...Ch. 16.13 - Draw the structure of an optically active fat...Ch. 16.14 - Show how each of the following esters could he...Ch. 16.14 - Prob. 39PCh. 16.15 - Prob. 40PCh. 16.15 - Which of the following reactions leads to the...Ch. 16.16 - Prob. 42PCh. 16.16 - Prob. 43PCh. 16.18 - Prob. 44PCh. 16.18 - Prob. 45PCh. 16.19 - Prob. 46PCh. 16.19 - Which alkyl halides from the carboxylic acids...Ch. 16.20 - Prob. 49PCh. 16.20 - Prob. 50PCh. 16.20 - Prob. 51PCh. 16.21 - Prob. 52PCh. 16.21 - Prob. 53PCh. 16.22 - How could you synthesize the following compounds...Ch. 16 - Prob. 55PCh. 16 - Name the following:Ch. 16 - Prob. 57PCh. 16 - What compound are obtained from the fallowing...Ch. 16 - a. Rank the following esters in order of...Ch. 16 - Because bromocyclohexane is a secondary alkyl...Ch. 16 - a. Which compound would you expect to have a...Ch. 16 - How could you use 1H NMR spectroscopy to...Ch. 16 - Prob. 63PCh. 16 - a. When a carboxylic acid is dissolved in...Ch. 16 - Rank the following compounds in order of...Ch. 16 - Prob. 66PCh. 16 - Prob. 67PCh. 16 - Prob. 68PCh. 16 - A compound with molecular formula C5H10O2 gives...Ch. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - Prob. 72PCh. 16 - Two products, A and B, are obtained from the...Ch. 16 - Prob. 74PCh. 16 - Prob. 75PCh. 16 - Prob. 76PCh. 16 - Prob. 77PCh. 16 - When treated with an equivalent of methanol,...Ch. 16 - a. Identify the two products obtained from the...Ch. 16 - Prob. 80PCh. 16 - Identity the major and minor products of the...Ch. 16 - Prob. 82PCh. 16 - When a compound with molecular formula C11H14O2...Ch. 16 - Prob. 84PCh. 16 - Prob. 85PCh. 16 - The 1H NMR spectra for two esters with molecular...Ch. 16 - Show how the following compounds could be prepared...Ch. 16 - Prob. 88PCh. 16 - Prob. 89PCh. 16 - Prob. 90PCh. 16 - The intermediate shown here is formed during the...Ch. 16 - Prob. 92PCh. 16 - Propose a mechanism that accounts for the...Ch. 16 - Catalytic antibodies catalyze a reaction by...Ch. 16 - Prob. 95P
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