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p-Xylene undergoes nitration much faster than benzene. Use

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

Solution for problem 3P Chapter 17

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 3P

Problem 3P

p-Xylene undergoes nitration much faster than benzene. Use resonance forms of the sigma complex to explain this accelerated rate.

Step-by-Step Solution:

Solution:

p-Xylene undergoes nitration much faster than benzene. Here we have to explain it in terms of  resonance structure.

Step 1

P-xylene undergoes  nitration to  gives 2-NOX (2-nitroxylene)

2o                     2o                         3o

Here the benzene sigma complex has  +ve charge on the 2o C-3 , C5 and another +ve charge on 3o carbon atom. Here the intermediate structure is more stable due to low activation energy. Thus the reaction rate will be faster.

Step 2 of 1

Chapter 17, Problem 3P is Solved
Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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p-Xylene undergoes nitration much faster than benzene. Use