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The light-initiated reaction of 2,3-dimethylbut-2-ene with

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

Solution for problem 9P Chapter 6

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 9P

The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide (NBS) gives two products:

Give a mechanism for this reaction, showing how the two products arise as a conse- quence of the resonance-stabilized intermediate.The bromination of cyclohexene using NBS gives only one major product, as shown on page 227. Explain why there is no second product from an allylic shift.
Step-by-Step Solution:

Solution 9P :

Step 1:

Given reaction :

The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide (NBS) gives two products:

(a) Give a mechanism for this reaction, showing how the two products arise as a consequence of the resonance-stabilized intermediate:

The propagation mechanism of the reaction is as shown below :

NBS produces low concentrations of Br2, so the mechanism shown here uses Br2 as the source of bromine, even though it originally came from NBS.

The resonance-stabilized allylic radical intermediate has radical character on both the 1o and 3o carbons, so bromine can bond to either of these carbons producing two isomeric products.

Step 2 of 2

Chapter 6, Problem 9P is Solved
Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

This full solution covers the following key subjects: bromosuccinimide, reaction, products, Product, NBS. 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 “?The light-initiated reaction of 2,3-dimethylbut-2-ene with N-bromosuccinimide (NBS) gives two products: 1. Give a mechanism for this reaction, showing how the two products arise as a conse- quence of the resonance-stabilized intermediate.2. The bromination of cyclohexene using NBS gives only one major product, as shown on page 227. Explain why there is no second product from an allylic shift.” is broken down into a number of easy to follow steps, and 59 words. The full step-by-step solution to problem: 9P from chapter: 6 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. Since the solution to 9P from 6 chapter was answered, more than 1286 students have viewed the full step-by-step answer. Organic Chemistry was written by and is associated to the ISBN: 9780321768414.

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The light-initiated reaction of 2,3-dimethylbut-2-ene with