EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
12th Edition
ISBN: 9781119233664
Author: Snyder
Publisher: VST
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Chapter 13, Problem 39P
Interpretation Introduction

Interpretation:

The order of reactivity of the given compounds in a Diels–Alder reaction is to be ranked along with explanation.

Concept introduction:

舧 Diels–Alder is a type of organic reaction in which substituted alkene and conjugated diene react to form substituted cyclohexene derivative. It is a single step reaction.

舧 The general reaction of Diels–Alder is as follows:

EBK ORGANIC CHEMISTRY, Chapter 13, Problem 39P

舧 The Diels–Alder reaction is between a conjugate diene and a reactant containing double bond (dienophile) to form the product and the product is called adduct.

舧 Diels–Alder reactions are highly stereospecific. The configuration of dienophile is retained in the product and the reaction is syn addition.

舧 The dienes react with dienophiles in cis forms rather than trans forms

舧 Endo and exo refers to the orientation of dienophile and its electron withdrawing group, when it reacts with a diene in Diels Alder reaction.

舧 The reaction with orientation of electron withdrawing group of dienophiles under the π orbitals of the diene, is Endo.

舧 The reaction with orientation of electron withdrawing group of dienophiles away from the π orbitals of the diene, is Exo

舧 Endo is favored in the transition state of Diels–Alder reaction because of its lower energy.

舧 If a compound is stable, it has lower energy and if a compound is unstable, it has higher energy.

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EBK ORGANIC CHEMISTRY

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