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Tetraphenylcyclopentadienone is a good Diels-Alder diene because the double bonds are in the S-Cis configuration. TRUE FALSE

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Final answer:

FALSE

Tetraphenylcyclopentadienone being in the S-cis configuration does not necessarily make it a good Diels-Alder diene, as its bulky substituents can hinder the required conformation for the reaction.

Step-by-step explanation:

The statement that tetraphenylcyclopentadienone is a good Diels-Alder diene because the double bonds are in the S-cis configuration is FALSE. This is because in a Diels–Alder reaction, the diene must be able to adopt the s-cis conformation, which allows the p orbitals on the adjacent carbons to overlap with the p orbitals of the dienophile, thus forming the six-membered ring. However, the bulky phenyl groups in tetraphenylcyclopentadienone would sterically hinder rotation into the s-cis conformation, making it less reactive or even possibly unable to participate in the reaction as a diene.

In the context of cis/trans stereoisomerism, it is essential to distinguish that while the cis configuration refers to substituents on the same side of a double bond or cycloalkane, the term 'S-cis' specifically describes the conformation where the diene's double bonds are conformationally oriented so that they can participate in a Diels-Alder reaction. The S-cis conformation is necessary for the diene's p orbitals to effectively overlap with those of the dienophile.

User Florian Blume
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