(a)
Interpretation:
The major product for the given Diels-Alder reaction is to be predicted.
Concept introduction:
Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene derivative. The dienophile adds to one side of the diene, and the diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.
(b)
Interpretation:
The major product for the given Diels-Alder reaction is to be predicted.
Concept introduction:
Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and the diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.
(c)
Interpretation:
The major product for the given Diels-Alder reaction is to be predicted.
Concept introduction:
Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and the diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.
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Chapter 15 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
- 2) Rank the following dienes in order of increasing rate of Diels-Alder reaction with maleic anhydride. You do not need to explain your ranking. H3C. H3CO Diene A Diene B Diene Carrow_forwardThis is a Diels-Alder reaction between ethylene and cis-1,3-butadiene. For each cycloaddition product, draw in all hydrogen atoms, and write the molecular formula below.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 0"C Diels-Alder adductarrow_forward
- The 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_forwardAlthough the Diels–Alder reaction generally occurs between an electronrich diene and an electron-deficient dienophile, it is also possible to have inverse-demand Diels–Alder reactions between suitable electrondeficient conjugated double bonds and electron-rich alkenes. These reactions are particularly useful because they allow for the incorporation of heteroatoms into the new six-membered ring. Predict the products of each inverse-demand Diels–Alder reaction below. Be sure your products reflect the correct stereochemistry. If more than one regioisomer is possible, draw both.arrow_forwardDraw the reactants that would react to form this cyclohexene derivative in a Diels-Alder reaction. Include any relevant stereochemical configurations.arrow_forward
- For the Diels-Alder reaction, the product's skeletal structure and configuration at the bridgehead carbons are given (and the given wedge bond and dash bond should not be changed). Complete the structure of the major product. Indicate the stereochemistry, by adding two wedge and two dash bonds, at only the fused-ring stereocenters. A Complete the product and clearly show stereochemistry. Select Draw Rings More H G = H C H 0 ° Erase Q2 Qarrow_forwardThis is a Diels-Alder reaction between cyclopentadiene and maleic anhydride (endo and exo products). For each cycloaddition product, draw in all hydrogen atoms, and write the molecular formula below.arrow_forwardThis is a Diels-Alder reaction between furan + maleic anhydride (endo and exo products). For each cycloaddition product, draw in all hydrogen atoms, and write the molecular formula below.arrow_forward
- For the Diels-Alder reactions show the major organic product. Be sure to show all stereochemistry where appropriate with wedged and dashed bonds. You do not need to show the mechanism. - HO IncBook Airarrow_forwardDraw the reactants that would react to form this cyclohexene derivative in Diels-Alder reaction. Include any relevant stereochemical configurations. Show your work.arrow_forward10. The following compound was produced in a Diels-Alder reaction. COOH a) How many sp³ hybridized carbons are in this molecule? b) Is this molecule chiral? c) Are the carboxylic acid substituents electron donating group or electron withdrawing group? d) Draw the diene and dienophile which would react together to give this product.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning