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(a) The solution given for Solved 20-1 was missing some

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

Solution for problem 17P 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 17P

(a) The solution given for Solved Problem 20-1 was missing some important resonance forms of the intermediates shown in brackets. Complete this mechanism by drawing all the resonance forms of these intermediates. Do your resonance forms help to explain why this reaction occurs under very mild conditions (water with a tiny trace of acid)?

(b) Finish the solution for Solved Problem 20-1 by providing a mechanism for the acidcatalyzed hydrolysis of ethyl formate.

Reference: Problem 20-1:

Draw the structures of the following carboxylic acids.

(a) α-methylbutyric acid

(b) 2-bromobutanoic acid

(c) 4-aminopentanoic acid

(d) cis-4-phenylbut-2-enoic acid

(e) trans-2-methylcyclohexanecarboxylic acid

(f) 2,3-dimethylfumaric acid

(g) m-chlorobenzoic acid

(h) 3-methylphthalic acid

(i) β-aminoadipic acid

(j) 3-chloroheptanedioic acid

(k) 4-oxoheptanoic acid

(l) phenylacetic acid

Step-by-Step Solution:
Step 1 of 3

Step-1

(a)It is known that greater the number of resonance structures , more stable the intermediate. The more stable the intermediate, the more easily it can be formed under mild condition. Here the intermediates are highly stabilized due to delocalization of the positive charge over the carbon and oxygen atom.

                                    (1st intermediate)

                                  (2nd Intermediate)

Step-2

(b)Here we have to write a mechanism for the acid catalyzed hydrolysis of ethyl formate:-

Ethyl formate on acid hydrolysis forms formic acid as the product. Acid hydrolysis is a process in which a protic acid is used to catalyze the cleavage of a chemical bond via a nucleophilic substitution reaction, with the addition of the elements of water (H2O).

Here H-A represents an acid. Ethyl formate on addition with  an acid forms an intermediate, which undergoes nucleophilic substitution reaction on addition with water molecule and in presence of ethanol to form formic acid as the product.

Step-3

Here we have to draw structure of the following carboxylic acids

(a) α-methylbutyric acid

(b)2-bromobutanoic acid

(c)4-aminopentanoic acid

Step 2 of 3

Chapter 20, Problem 17P is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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(a) The solution given for Solved 20-1 was missing some

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