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Four compounds are shown. These compounds react more

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

Solution for problem 29SP Chapter 16

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 29SP

Four compounds are shown. These compounds react more quickly, or they react with more favorable equilibrium constants, than similar compounds with less conjugated systems. In each case, explain the enhanced reactivity.

Step-by-Step Solution:
Step 1 of 3

Here we have to compare the reactivity of  both the compounds.

Step-1

Here H-A is the general form of an acid. In between this two resonance structures, the 1st resonance structure is aromatic  and the second one is nonaromatic .Thus the 1st compound is more stable than the 2nd one because in the 2nd structure the protonation has been carried out on a singly bonded oxygen atom and generate an unstable product whereas in the 1st compound the cation produced is aromatic and resonance stabilized. Thus the 1st compound is more basic  than the the second compound.

Step-2

Here both the structures are resonance stabilized, but the 1st compound is aromatic whereas the 2nd compound is aliphatic.  An aromatic compound is more stable than that of an aliphatic compound.  It is known that the reaction that produces more stable product will usually carried out faster under mild condition and having lower activation energy. Thus the 1st compound ionizes more readily than that of the second compound.

Step-3

Step 2 of 3

Chapter 16, Problem 29SP is Solved
Step 3 of 3

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

Organic Chemistry was written by and is associated to the ISBN: 9780321768414. Since the solution to 29SP from 16 chapter was answered, more than 258 students have viewed the full step-by-step answer. The full step-by-step solution to problem: 29SP from chapter: 16 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. This full solution covers the following key subjects: compounds, react, less, constants, enhanced. 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 answer to “Four compounds are shown. These compounds react more quickly, or they react with more favorable equilibrium constants, than similar compounds with less conjugated systems. In each case, explain the enhanced reactivity.” is broken down into a number of easy to follow steps, and 31 words.

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