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Chemistry / Organic Chemistry 8 / Chapter 17 / Problem 5P

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

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(a) Draw a detailed mechanism for the FeBr3-catalyzed

Chapter 11, Problem 5P

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Problem 5P

(a) Draw a detailed mechanism for the FeBr3-catalyzed reaction of ethylbenzene with bromine, and show why the sigma complex (and the transition state leading to it) is lower in energy for substitution at the ortho and para positions than it is for substitution at the meta position.

(b) Explain why m-xylene undergoes nitration 100 times faster than p-xylene.

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QUESTION:

Problem 5P

(a) Draw a detailed mechanism for the FeBr3-catalyzed reaction of ethylbenzene with bromine, and show why the sigma complex (and the transition state leading to it) is lower in energy for substitution at the ortho and para positions than it is for substitution at the meta position.

(b) Explain why m-xylene undergoes nitration 100 times faster than p-xylene.

ANSWER:

Solution 5P

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