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Diel's Alder Reaction: Department of Pharmaceutical Chemistry

This document summarizes a seminar on the Diels-Alder reaction presented by Mr. Andhale Ganesh Sakharam. The Diels-Alder reaction involves the addition of a diene to a dienophile to form a cyclic compound. It is a concerted reaction where bonds break and form simultaneously. The reaction is initiated by heat and forms new six-membered rings. Electron-withdrawing groups on the dienophile increase its reactivity. The stereochemistry of the dienophile is retained in the product. Common dienes and dienophiles that participate in Diels-Alder reactions are discussed.

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181 views16 pages

Diel's Alder Reaction: Department of Pharmaceutical Chemistry

This document summarizes a seminar on the Diels-Alder reaction presented by Mr. Andhale Ganesh Sakharam. The Diels-Alder reaction involves the addition of a diene to a dienophile to form a cyclic compound. It is a concerted reaction where bonds break and form simultaneously. The reaction is initiated by heat and forms new six-membered rings. Electron-withdrawing groups on the dienophile increase its reactivity. The stereochemistry of the dienophile is retained in the product. Common dienes and dienophiles that participate in Diels-Alder reactions are discussed.

Uploaded by

minhhasfone
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
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A Seminar On Department of

Diel’s Alder Reaction Pharmaceutical


Chemistry

Advanced
Pharmaceutical
chemistry

By Mr. Andhale Ganesh


Sakharam
Ist year M. Pharm
ABMRCOP
24/2/2009
Reactions of Organic Compounds
Introduction

The Diels-Alder reaction is a method of producing cyclical organic


compounds (a cycloaddition reaction), and is named for Otto Diels
and Kurt Alder who in 1950 received the Nobel Prize for their
experiments.

It is a pericyclic reaction, meaning it goes on in one step with a


cyclic flow of electrons, and involves the addition of a diene
molecule to a dienophile (literally, diene loving molecule).
Diel’s Alder reaction

Two different  bond-containing molecules react to form


a cyclic compound
Conjugated Dienes
• Conjugated dienes are compounds having two double
bonds joined by one  bond.
• Conjugated dienes are also called 1,3-dienes.
• Three stereoisomers are possible for 1,3-dienes with alkyl
groups bonded to each end carbon of the diene.

6
Dienes:

MeO MeO

S O O

Dienophiles:
N N N
H H H C H H C H H C
C C C C C
C C C C C
H H H H C C H C H C
N N N N
All Diels-Alder reactions have the following features in
common:
1. They are initiated by heat; that is, the Diels-Alder
reaction is a thermal reaction.
2. They form new six-membered rings.
3. Three  bonds break, and two new C—C  bonds and
one new C—C  bond forms.
4. They are concerted; that is, all old bonds are broken
and all new bonds are formed in a single step.

8
Some examples of Diels-Alder reactions are shown below:

9
Several rules govern the course of the Diels-Alder
reaction.

1. The diene can react only when it adopts the s-cis


conformation.

10
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2. Electron-withdrawing substituents in the dienophile
increase the reaction rate.

• In a Diels-Alder reaction, the conjugated diene acts as a


nucleophile and the dienophile acts as an electrophile.
• Electron-withdrawing groups make the dienophile more
electrophilic (and thus more reactive) by withdrawing
electron density from the carbon-carbon double bond.
• If Z is an electron-withdrawing group, then the reactivity
of the dienophile increases as follows:

12
A carbonyl group is an effective electron-withdrawing
group because it bears a partial positive charge (+),
which withdraws electron density from the carbon-
carbon double bond of the dienophile.

Common dienophiles in the Diels-Alder reaction

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3. The stereochemistry of the dienophile is retained.

14
References
1.Organic Chemistry Reaction and
Reagents,O.P.Agrawal,Page
no.278-282.
2.Organic Reaction Mechanism; Third
Edition;V.K.Ahluwalia, Rakesh kumar
Parashar, page no.612-617.
THANK YOU

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