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SolutionsExamples

1. Retrosynthesis

Carry out a retrosynthetic analysis: draw the structures of the diene and dienophile that lead to each Diels-Alder adduct.

Twelve Diels-Alder adducts, each followed by a retrosynthetic arrow
The starting dienes and dienophiles, including butadiene, cyclopentadiene, benzyne, phenylacetylene, 9-methylanthracene and tetracyanoethylene

To find them, look for the cyclohexene in the adduct: the ring double bond comes from the central carbons of the diene, and the two carbons opposite to it come from the dienophile.

2. Adduct with an alkyne

What is obtained from 1,3-butadiene with dimethyl acetylenedicarboxylate, MeO2C–C≡C–CO2Me?

Dimethyl cyclohexa-1,4-diene-1,2-dicarboxylate: one double bond of the adduct remains from the triple bond of the dienophile.

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