The structures of the product when 1,3-butadiene reacts with the given dienophiles are to be given. 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.

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Chapter 13, Problem 40P

Interpretation Introduction

Interpretation:

The structures of the product when 1,3-butadiene reacts with the given dienophiles are to be given.

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.

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5. Please draw in the blanks the missing transition states and the correlated products. Explicitly display relevant absolute stereochemical configuration. MeOH I OMe H Endo transition state, dienophile approaching from the bottom of diene + H ཎྞཾ ཌཱརཱ༔,_o OMe H H OMe Endo transition state, dienophile approaching from the top of diene or from the bottom but horizontally flipped (draw one) + Exo transition state, dienophile approaching from the top of diene or from the bottom but horizontally flipped (draw one) Exo transition state, dienophile approaching from the top of diene or from the bottom but horizontally flipped (draw one) MeO H H MeO H MeO H MeO H H