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Chapter 14: 31Ea (page 447)

Predict the products of the following Diels-Alder reaction:


Short Answer

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Diels-Alder reaction was discovered by the German chemists Otto Diels and Kurt-Alder in 1928. Diels-Alder reaction is an important cycloaddition reaction which is stereospecific. It includes a substituted alkene in the form of a dienophile and a conjugated diene. It proceeds via concerted mechanism. Diels alder reaction can be used to generate 6 membered rings since there is a simultaneous construction of two new Carbon-carbon bonds.Stereochemistry of the dienophile is retained.

Step by step solution

01

Diels-Alder reaction

Diels-Alder reaction was discovered by the German chemists Otto Diels and Kurt-Alder in 1928. Diels-Alder reaction is an important cycloaddition reaction which is stereospecific. It includes a substituted alkene in the form of a dienophile and a conjugated diene. It proceeds via concerted mechanism. Diels alder reaction can be used to generate 6 membered rings since there is a simultaneous construction of two new Carbon-carbon bonds.Stereochemistry of the dienophile is retained.

02

Diene and dienophile

Diene is an organic compound which comprises of two conjugated pi bonds (4 pi bonds) while dienophile is a diene loving compound containing 2 pi electrons.

The diene is

Dienophile is

03

Prediction of product

The reaction is stereospecific (single stereoisomer is obtained) .Endo product is formed as a result of Diels-Alder reaction. A substituent on one bridge is endo when it is cis to the larger of the other two bridges.

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Most popular questions from this chapter

Draw and name the six possible diene isomers of formula. Which of the six are conjugated dienes?

Allene, CH2=C=CH2has a heat of hydrogenation of -298kJ/mol

(-71.3kcal/mol). Rank a conjugated diene, a nonconjugated diene, and an

allene in order of stability.

Would you expect a conjugated diyne such as 1,3-butadiyne to undergo Diels-Alder reaction with a dienophile? Explain.

Adiponitrile, a starting material used in the manufacture of nylon, can be prepared in three steps from 1,3-butadiene. How would you carry out this synthesis?

How could you use Diels-Alder reactions to prepare the following products ? Show the starting diene and dienophile in each case.

a)
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