SME
Organic Chemistry II · Problem type
Can it be the diene in a Diels–Alder?
Use this for “Can 1,3-cyclohexadiene, 1,4-pentadiene and isoprene each act as the diene in a Diels–Alder reaction?”
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Can it be the diene in a Diels–Alder reaction?
Tap a card, then tap its group.
Ask: are the two C=C conjugated? If so, is the s-cis shape locked by a ring, or reached by turning?
Assumptions
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The diene must have two C=C bonds joined by one single bond, and must react in the s-cis shape, both ends on the same side.
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A ring that holds the two C=C on the same side locks the diene s-cis, so it reacts fast; an open chain must first turn about its middle bond.
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Benzene’s C=C are part of its aromatic ring, and losing that stability blocks the reaction.
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