Concept explainers
Interpretation:
The structure of the productformed by intramolecular Diels–-Alder reaction of the given compound at room temperature is to be drawn.
Concept introduction:
>The conjugate addition of
Dienophile is the alkene that adds to diene.Diene is an electron-rich system attacksan electron deficient dienophile.The diene and dienophile, when residing in a single molecule, the intramolecular Diels–-Alder reaction is possible.
>In order to form the cyclic transition state in Diels–-Alder reaction, the conjugated diene must be able to adopt
The
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Organic Chemistry - Standalone book
- ) 1) Provide the structure of the major product, which results from Diels-Alder reaction. Draw the structure of the MOST stable product that results when the diene shown is treated with HBr at 80°C. HBr 80 °C CH3 Diels-Alder Reaction Provide the structure of the major organic product in the following reaction. XOarrow_forwardWhen heated, allyl aryl ethers and allyl vinyl ethers undergo a reaction called a Claisen rearrangement, a concerted reorganization of bonding electrons similar to the Diels-Alder reaction. The reaction proceeds through a six-membered, cyclic transition state. Draw the structure of the expected product when this compound undergoes a Claisen rearrangement. You do not have to consider stereochemistry. For the purposes of this problem, assume that double bonds in an aromatic ring are localized at the positions indicated in the figure. Include isomerization to a phenol IF appropriate.arrow_forwardOne step in the synthesis of dodecahedrane (Section 4.11) involves reaction of the tetraene C with dimethylacetylene dicarboxylate (D) to afford two compounds having molecular formula C16H16O4. This reaction has been called a domino Diels–Alder reaction. Identify the two products formed.arrow_forward
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- Draw the products of the following Diels–Alder reactions. Indicate stereochemistry where appropriate.arrow_forwardShow how the following starting materials are converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.arrow_forwardThe following compound undergoes an intramolecular Diels-Alder reaction to give a tricyclic product. Propose a structural formula for the product. heat An intramolecular Diels-Alder adductarrow_forward
- Indicate the reagents (diene and phyllodiene) necessary to obtain the following compound by a Dirls-Alder reaction. CH3 CH3 COOH COOHarrow_forwardShow how the following starting material is converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.arrow_forward2) Rank the following dienes by how rapidly they will undergo Diel-Alder reactions with ethylene.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning