The products and transition states for Diels–Alder reaction of the given reactants are to be determined. Concept introduction: 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. The general reaction of Diels–Alder is as follows: 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. Diels–Alder reactions are highly stereospecific. The configuration, if dienophile is retained in the product and the reaction, is syn addition. The dienes react with dienophiles in cis forms rather than trans forms. Endo and exo refers to the orientation of dienophile and its electron withdrawing group, when it reacts with a diene in Diels–Alder reaction. The reaction with orientation of electron withdrawing group of dienophiles under the π orbitals of the diene is endo. The reaction with orientation of electron withdrawing group of dienophiles away from the π orbitals of the diene is exo. Endo is favored in the transition state of Diels–Alder reaction because of its lower energy. If a compound is stable, it has lower energy and if a compound is unstable, it has higher energy.

Question

Want to see the full answer?

Answer 1

Question

Chapter 13, Problem 17PP

Interpretation Introduction

Interpretation:

The products and transition states for Diels–Alder reaction of the given reactants are to be determined.

Concept introduction:

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.

The general reaction of Diels–Alder is as follows:

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.

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

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

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

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

The reaction with orientation of electron withdrawing group of dienophiles away from the π orbitals of the diene is exo.

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

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

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Practice Problem 13.36b Problem 13.34 outlines a general method for the preparation of cis- or trans-disubstituted epoxides. Using that method, identify what reagents you would use to prepare the following epoxide from acetylene: H" 'Et The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B C D DMP or PCC На, Pt EtBr PHCH2BR E F H H2SO4, H20, HgSO4 МСРВА (RCO3зН) Na, NH3 (/) H2, Lindlar's cat. I K TSCI, py PhBr NANH2 1) EtMgBr; 2) H30+

8. (a) Benzene derivatives exhibit medium to strong absorption in UV-region. Explain why aniline and phenoxide ion have strong UV-absorptions.

The following triene undergoes an intramolecular Diels-Alder reaction to give a bicyclic product. Propose a structural formula for the product. Account for the observation that the Diels-Alder reaction given in this problem takes place under milder conditions (at lower temperature) than the analogous Diels-Alder reaction 0"C Diels-Alder adduct