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Conjugated Alkadienes: Preparation & Reactivity

This document covers Chapter 7 on Conjugated Alkadienes in Organic Chemistry, detailing their preparation methods and reactivity. It discusses electrophilic addition, the Diels-Alder reaction, and polymerization processes. The chapter highlights the importance of stereochemistry and the role of electron-withdrawing groups in enhancing reactivity.

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tridung12062004
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34 views16 pages

Conjugated Alkadienes: Preparation & Reactivity

This document covers Chapter 7 on Conjugated Alkadienes in Organic Chemistry, detailing their preparation methods and reactivity. It discusses electrophilic addition, the Diels-Alder reaction, and polymerization processes. The chapter highlights the importance of stereochemistry and the role of electron-withdrawing groups in enhancing reactivity.

Uploaded by

tridung12062004
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

ORGANIC CHEMISTRY

OCHE220203
Lecturer: Dat P. Nguyen, Ph.D
Email: datnp@[Link]
Department of Chemical Technology
Faculty of Chemical and Food Technology 1
CHAPTER 7
CONJUGATED
ALKADIENES

2
CONTENTS

1. Preparation of Conjugated Alkadienes


2. Reactivity of Conjugated Alkadienes
2.1. Electrophilic Addition
2.2. Diels-Alder Reaction
2.3. Polymerization of Conjugated Alkadienes

3
1. Preparation of Conjugated Alkadienes

Alkynes

Halides/
hydrogenation Aldehydes/
Alcohols/
Ketones
Amines
elimination Wittig reaction

Alkenes

Preparation methods of conjugated alkadienes are the


same with alkenes
4
2. Reactivity of Conjugated Alkadienes

Electrophilic Addition
(AE)

Diels-Alder Reactions

Conjugated Alkadienes

Polymerization

Oxidation

5
2. Reactivity of Conjugated Alkadienes
2.1. Electrophilic Addition

Reaction with halogen

6
2. Reactivity of Conjugated Alkadienes
2.1. Electrophilic Addition

Reaction with HX

7
2. Reactivity of Conjugated Alkadienes
2.1. Electrophilic Addition

Reaction with HX

8
2. Reactivity of Conjugated Alkadienes
2.1. Electrophilic Addition

Reaction with HX – Mechanism

9
2. Reactivity of Conjugated Alkadienes
2.1. Electrophilic Addition

Reaction with HX – Mechanism

thermodynamically
stable
product

kinetically
stable
product
10
2. Reactivity of Conjugated Alkadienes
2.2. Diels-Alder Reaction

Diels-Alder Reaction

11
2. Reactivity of Conjugated Alkadienes
2.2. Diels-Alder Reaction

Dienophile

Reactivity of the dienophile is increased if 1 or more


electron-withdrawing groups are present 12
2. Reactivity of Conjugated Alkadienes
2.2. Diels-Alder Reaction

Stereochemistry

13
2. Reactivity of Conjugated Alkadienes
2.2. Diels-Alder Reaction

Stereochemistry
In order to participate in a Diels-Alder reaction, the diene
must be in an s-cis conformation

14
2. Reactivity of Conjugated Alkadienes
2.2. Diels-Alder Reaction

Stereochemistry

15
2. Reactivity of Conjugated Alkadienes
2.3. Polymerization of Conjugated Alkadienes

16

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