Diels Alder Reaction of Tetraphenylcyclopentadienone Purpose of the Experiment: To successfully synthesize dimethyltetraphenylphthalate via a Diels Alder reaction. The melting point of the product is 258oC.  Why should we not do a melting point of the product? The intermediate in brackets loses CO to form the product at 180oC.  If the C=O were replaced by CH2, do you think the same type of reaction would happen with loss of :CH2?

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter9: Nucleophilic Substitution And Β-elimination
Section9.7: Experimental Evidence For E1 And E2 Mechanisms
Problem 9.7P
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Diels Alder Reaction of Tetraphenylcyclopentadienone

Purpose of the Experiment: To successfully synthesize dimethyltetraphenylphthalate via a Diels Alder reaction.

  1. The melting point of the product is 258oC.  Why should we not do a melting point of the product?
  2. The intermediate in brackets loses CO to form the product at 180oC.  If the C=O were replaced by CH2, do you think the same type of reaction would happen with loss of :CH2?

 

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