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: 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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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:

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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Rank the following dienes in their rate of reaction with the same dienophile in a Diels-Alder reaction. For example, 1 = fastest or most reactive diene, 4 = slowest or least reactive diene.

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Diels—Alder reaction of a monosubstituted diene (such as CH2 = CH – CH = CHOCH3) with a monosubstituted dienophile (such as CH2 = CHCHO) gives a mixture of products, but the 1,2-disubstituted product often predominates. Draw the resonance hybrid for each reactant and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.