Interpretation: The diene and the dienophile that might be used to prepare the given racemic Diels-Alder adduct have to be found.
Concept Introduction:
Diels-Alder reaction:
It is the reaction of conjugated dienes with double or triple bonded compounds which are known as “dienophiles”. The reaction is a
Example:
Diels-Alder reaction to form bicyclic system:
The Diels-Alder adduct formed in the Diels-Alder reaction can also be a bicyclic system which will be obtained when cylopentadiene is used as the diene as shown here:
In this reaction, the cylopentadiene acts as both diene and dienophile and formed a bicyclic system. When it is heated to
Racemic mixture in Diels-alder reaction:
In the Diels-alder reaction, the formation of two new sigma bonds results in the formation of two new chiral centres that are enantiomers to each other. So, the Diels-alder adduct is the mixture of two enantiomers and therefore it is being a racemic Diels-alder adduct.
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Chapter 20 Solutions
Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- What reactants are expected to afford the following Diels-Alder adduct? H. H;C H. 請arrow_forwardThe following triene undergoes an intramolecular Diels-Alder reaction to give a bicyclic product. Propose a structural formula for the product. Account for the observation that the Diels-Alder reaction given in this problem takes place under milder conditions (at lower temperature) than the analogous Diels-Alder reaction shown in Problem 20.34.arrow_forward3) How could you use Diels-Alder reactions to prepare the following products? Show the starting diene and dienophile in each case H a. b. C. H H d. H .CO₂CH3 CNarrow_forward
- Which constitutional isomer represents the product of this Diels-Alder reaction?arrow_forwardWhat diene and dienophile would react to give the following Diels-Alder product? O. O 1 O 2 O 4 O 5 O 3arrow_forwardThe Diels-Alder reaction is not limited to making six-membered rings with only carbon atoms. Predict the products of the following reaction that produce rings with atoms other than carbon in them.arrow_forward
- 6. Predict the major product for the following Diels-Alder reaction. 7. Which diene and dienophile would react to give the following Diels-Alder product? Сон 8. Which diene and dienophile would react to give the following Diels-Alder product? Illarrow_forward3. Predict the products of the following Diels-Alder reactions. a. NC a. 4. Identify the diene and dienophile used to make these Diel-Alder products. CN CH3 CN CH 3 CO₂CH3 CO₂CH3arrow_forwardWhich of the following diene(s) cannot undergo the Diels-Alder reaction? II IV %3Darrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning