Answered: Of the three 1,4-diphenyl-1,3-butadiene…

Of the three 1,4-diphenyl-1,3-butadiene isomers (E,E or E,Z or Z,Z) indicate the most suitable diene that can be used as a reactant in a Diels-Alder reaction.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

Section14.SE: Something Extra

Problem 34AP

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Of the three 1,4-diphenyl-1,3-butadiene isomers (E,E or E,Z or Z,Z) indicate the most suitable diene that can be used as a reactant in a Diels-Alder reaction. Explain your choice.

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Following is an example of a type of reaction known as a Diels-Alder reaction 1,3-Pentadiene Ethylene 3-Methylcyclohexene (a racemic mixture) The Diels-Alder reaction between a diene and an alkene is quite remarkable in that it is one of the few ways that chemists have to form two new carbon-carbon bonds in a single reaction. Given what you know about the relative strengths of carbon-carbon sigma and pi bonds, would you predict the Diels-Alder reaction to be exothermic or endothermic? Explain your reasoning.
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Step 6: Now that you have determined the substrates and mechanism of a Diels-Alder reaction, you will learn how to recognize when you should use the Diels-Alder reaction. In a synthesis reaction, if you are given a cyclohexene product with no other obvious functional group transformations and an electron-withdrawing group two carbons away from the alkene, it is likely made via the Diels-Alder reaction. Deduce the structures of the starting materials to form the Diels-Alder adduct shown. ..... CN CN Diene + Dienophile
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