Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition
Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition
3rd Edition
ISBN: 9780134255644
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
Question
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Chapter 11.8, Problem 16P

(a)

Interpretation Introduction

Interpretation:

To predict the products of the following transesterification reaction.

  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,

Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition, Chapter 11.8, Problem 16P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

To predict the products of the following transesterification reaction.

  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,

Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition, Chapter 11.8, Problem 16P , additional homework tip  2

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What spectral features allow you to differentiate the product from the starting material? Use four separate paragraphs for each set of comparisons. You should have one paragraph each devoted to MS, HNMR, CNMR and IR. 2) For MS, the differing masses of molecular ions are a popular starting point. Including a unique fragmentation is important, too. 3) For HNMR, CNMR and IR state the peaks that are different and what makes them different (usually the presence or absence of certain groups). See if you can find two differences (in each set of IR, HNMR and CNMR spectra) due to the presence or absence of a functional group. Include peak locations. Alternatively, you can state a shift of a peak due to a change near a given functional group. Including peak locations for shifted peaks, as well as what these peaks are due to. Ideally, your focus should be on not just identifying the differences but explaining them in terms of functional group changes.

Chapter 11 Solutions

Essential Organic Chemistry Study Guide & Solution Manual, Books a la Carte Edition

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