EBK ESSENTIAL ORGANIC CHEMISTRY
EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: Bruice
Publisher: PEARSON
Question
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Chapter 11.8, Problem 13P

(a)

Interpretation Introduction

Interpretation:

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

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 promotes the protonation of oxygen atom in 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 of oxygen atom 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,

EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 11.8, Problem 13P , 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 ester.

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 promotes the protonation of oxygen atom in 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 of oxygen atom 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,

EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 11.8, Problem 13P , 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 ester.

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 promotes the protonation of oxygen atom in 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 of oxygen atom 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,

EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 11.8, Problem 13P , 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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Done 11:14 ⚫ worksheets.beyondlabz.com 5 (a). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 6 5 (b). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 7 6. Are there any differences between the spectra you obtained in Beyond Labz and the predicted spectra? If so, what were the differences? <
2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity

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