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The mechanism of the Fischer esterification was

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 16P Chapter 20

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 16P

The mechanism of the Fischer esterification was controversial until 1938, when Irving Roberts

and Harold Urey of Columbia University used isotopic labeling to follow the alcohol oxygen

atom through the reaction. A catalytic amount of sulfuric acid was added to a mixture of 1 mole

of acetic acid and 1 mole of special methanol containing the heavy isotope of oxygen.

After a short period, the acid was neutralized to stop the reaction, and the components of the

mixture were separated.

(a) Propose a mechanism for this reaction.

(b) Follow the labeled 18O atom through your mechanism, and show where it will be found

in the products.

(c) The 18O isotope is not radioactive. Suggest how you could experimentally determine the

amounts of 18O in the separated components of the mixture.

Step-by-Step Solution:
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Solution 16P

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Chapter 20, Problem 16P is Solved
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Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

The answer to “The mechanism of the Fischer esterification was controversial until 1938, when Irving Robertsand Harold Urey of Columbia University used isotopic labeling to follow the alcohol oxygenatom through the reaction. A catalytic amount of sulfuric acid was added to a mixture of 1 moleof acetic acid and 1 mole of special methanol containing the heavy isotope of oxygen.After a short period, the acid was neutralized to stop the reaction, and the components of themixture were separated. (a) Propose a mechanism for this reaction.(b) Follow the labeled 18O atom through your mechanism, and show where it will be foundin the products.(c) The 18O isotope is not radioactive. Suggest how you could experimentally determine theamounts of 18O in the separated components of the mixture.” is broken down into a number of easy to follow steps, and 121 words. Since the solution to 16P from 20 chapter was answered, more than 341 students have viewed the full step-by-step answer. This full solution covers the following key subjects: acid, mechanism, reaction, mixture, Mole. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. The full step-by-step solution to problem: 16P from chapter: 20 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. Organic Chemistry was written by and is associated to the ISBN: 9780321768414.

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