OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
8th Edition
ISBN: 9781305582439
Author: Brown, William H.; Iverson, Brent L.; Anslyn, Eric; Foote, Christopher S.
Publisher: Cengage Learning
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Chapter 8, Problem 8.32P

(a)

Interpretation Introduction

Interpretation:

Major product of the given reaction has to be identified.

Concept introduction:

HBr addition to alkene under radical condition:

Non-markonikov addition of HBr to alkenes occur by a radical mechanism in presence of peroxide, in which a Br· reacts with the π bond of the alkene to create a radical intermediate that H· from HBr to continue the chain process. The regioselectivity of the products is the opposite of the ordinary Markonikov addition products that form under polar conditions; hence it is useful alternative to polar addition of HBr in organic synthesis.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 8, Problem 8.32P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

Major product of the given reaction has to be identified.

Concept introduction:

HBr addition to alkene under radical condition:

Non-markonikov addition of HBr to alkenes occur by a radical mechanism in presence of peroxide, in which a Br· reacts with the π bond of the alkene to create a radical intermediate that H· from HBr to continue the chain process. The regioselectivity of the products is the opposite of the odinary Markonikov addition products that form under polar conditions; hence it is useful alternative to polar addition of HBr in organic synthesis.

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 8, Problem 8.32P , additional homework tip  2

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(a) (b) (c) Suggest a synthesis of the following alkene (A) using a Wittig reaction strategy. Draw the starting material(s), key reagent and a full reaction mechanism including an explanation of the observed geometry. Which of the following (B) and (C) will favour the enol form? Briefly explain your reasoning. Predict the product(s) and provide a mechanism for each of the following transformations: (i) (ii) OMe OMe Base OEt NaOEt
(b) (c) Suggest a synthesis of the following compound (D) which utilises a conjugate addition strategy. Explain your reasoning clearly by drawing the mechanism. D Ph3P Me Predict the product and provide a mechanism for each of the following transformations; (i) H
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