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Propose mechanisms to account for the observed products in

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

Solution for problem 74SP 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 74SP

Propose mechanisms to account for the observed products in the following reactions. In some cases more products are formed, but you only need to account for the ones shown here.

Step-by-Step Solution:
Step 1 of 3

Step-1

In this reaction N-bromosuccinimide (NBS) react with Br2 and generate bromine radical in presence of UV light. THe reaction has been carried out as follows:-

Step-2

(b)Here the allylic carbocation has two resonance forms in which both the resonance structure has positive sign on the C atom.

The ethanol nucleophile can attack either of these carbons and forms SN1 products or loss of an adjacent H will give E1 product.

Mechanism:-

SN1 reaction:

E1 product:-

Step-3

(c)

It is a 1st order solvolysis reaction and the 1st step involves ionization followed by rearrangement reaction.

Mechanism...

Step 2 of 3

Chapter 6, Problem 74SP is Solved
Step 3 of 3

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

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Propose mechanisms to account for the observed products in

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