Concept explainers
Interpretation:
In the Diels-Alder reaction, which interaction out of A and B leads to form the major product is to be explained.
Concept introduction:
Diels-Alder reactions are concerted and stereospecific. When the diene and the dienophile of a Diels–Alder reaction are both unsymmetric, the major isomeric product is the one produced by the approach that exhibits the more favorable electrostatic attraction among atoms undergoing bond formation. The oppositely charged species are attracted by each other, while there is a repulsive interaction between the same charged species. Therefore, the regiochemistry in Diels-Alder reaction depends on the nature of substituents on diene as well as that on dienophile. An electron-donating substituent on the diene and an electron-withdrawing substituent on the dienophile not only enhance the rate of given Diels-Alder reaction but also decide which isomer will form predominantly and the stereochemistry as well.
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ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
- Based on the given information, determine the diene and dienophile of the Diels-Alder reaction.arrow_forwardBASED ON THIS EXPERIMENT: The purpose of this experiment is to perform a Diels-Alder reaction between E,E-2,4-hexadien-1-ol and maleic anhydride in a "neat" or solventless condition. The Diels-Alder reaction is a [4+2] cycloaddition that forms a six-membered ring, typically a derivative of cyclohexene. The diene, E,E-2,4-hexadien-1-ol, and the dienophile, maleic anhydride, will be mixed and ground together, resulting in a eutectic mixture. The reaction is unique as it occurs without a solvent, contributing to a "greener" experiment. After the reaction, the product will be analyzed through mass measurements, and the mechanism involves a subsequent nucleophilic acyl substitution. QUESTION: how many carbon atoms does a dienophile contribute to the Diels-Alderadduct? How many carbon atoms does a diene contribute? draw andlabel which reagent is the diene, and which is the dienophile.arrow_forwardin a diels-alder reaction involving 2,3-dimethyl-1,3-butadiene and maleic anhydride, which is the diene and which is the dienophile?arrow_forward
- Which of the following compounds can arise directly from a Diels-Alder reaction? Circle any structures that can. Then, identify the appropriate diene(s) and dienophile(s) that would lead to the compound. Pay attention to E-/Z- stereochemistry in all of the reactants. For those that cannot undergo a Diels-Alder reaction, please explain why.arrow_forwardComplete the following Diels-Alder reaction by drawing a structure for the product formed. Consider the resonance in the diene and dienophile and draw partial charges at correct positions. That will help you in drawing the correct product.arrow_forwardDraw a Diels-Alder reaction that shows the stereospecificity of the reaction with respect to both the diene and dienophile, and that would follow the endo rule (show only the major product).arrow_forward
- A2 What is the inverse electron demand Diels–Alder reaction? Please pick a pair of a diene and a dienophile from the following dienes and dienophile that will undergo this type of reaction. Please show how this reaction works using Frontier Molecular Orbitals. What is the reaction product?arrow_forwardRank the following dienes from most reactive to least reactive in a Diels Alder reaction. please explain stepsarrow_forwardA Diels-Alder reaction that shows regioselectivity, but not stereoselectivityarrow_forward