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SolutionsStereochemistry

1. Stereochemistry and regiochemistry

Predict the result of the following processes:

Nine Diels-Alder reactions with numbered atoms: linear and cyclic dienes, with and without methyl or methoxy groups, with methyl vinyl ketone, ethene and acetylenedicarboxylate

Adducts with their stereochemistry: racemates, meso forms and endo adducts; the methoxy dienes give the

2. The "meta" adduct

Using resonance forms, suggest an explanation for the fact that the "meta" regioisomer is always disfavoured.

A diene with an OR group at position 2 and another with an OR at position 1 react with an enone to give the

Resonance forms: OR builds up negative charge on a particular diene carbon and the carbonyl positive charge on the β carbon of the dienophile; the oppositely charged carbons bond, giving the

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