Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 14, Problem 26P
Interpretation Introduction

Interpretation:

The difference in the stabilities ofcycloheptatrienone andcyclopentadienone needs to be explained and the structure of Diels–Alder adduct of cyclopentadienoneneeds to be drawn.

Concept introduction:

In accordance with theHuckel’s rule, aromatic compounds contain a planar ring and have a conjugated pi system with (4n+2)π electrons, where n=0,1,2,3,...

Anaromatic compound contains conjugated pi bonds.

Antiaromatic compounds contain (4n)π electrons. They are very unstable and are highly reactive.

Diels-Alder reaction is an addition reaction of a conjugated diene and an alkene to form a cyclohexene derivative. It is a single step reaction.

The general reaction of Diels–Alder is as follows:

Organic Chemistry, Chapter 14, Problem 26P

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 refer 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.

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Write the equation and the corresponding mechanisms for the Diels-Alder reactions ofcyclopentadiene with EACH of the following compounds:(a) Vinyl acetate(b) Acrylic acid(c) Dimethyl acetylenedicarboxylate
The Diels–Alder Reaction – A [4+2] Cycloaddition Experiment.    (a) Explain why the endo-rule is not obeyed when furan is used as the diene. Use chemical structures and models to support your answer.
(c) Diels-Alder reactions are a highly effective way to synthesise stereospecifically fused cyclic structures. (1) Using suitable diagrams, curly arrows and/or reaction schemes, explain why the reaction between cyclopentadiene and maleic anhydride favours formation of the endo product. (ii) If the reaction in part (i) were conducted using furan instead of cyclopentadiene, what difference would you observe in the product/s, with respect to their stereochemistry? (No need to draw reaction mechanisms) (iii) Draw the stereospecific 3D structure of the product formed during the Diels-Alder reaction below. (No need to show the reaction mechanism) Нeat Br Br (Figure Q11ciii)

Chapter 14 Solutions

Organic Chemistry

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