3. The Diels-Alder reaction is quite useful in preparing cyclic or polycylic compounds from dienes. However, the rate that the reaction can occur at, as well as the stereochemistry of the product, can depend on the starting materials used. a) Buta-1,3-diene, A, participates in Diels-Alder reactions, but much more slowly that cyclopentadiene, B, while the compound 3-methylidenecyclohexene, C, does not react at all. Explain the difference in reactivity of these three dienes in Diels- Alder reactions. B C b) Buta-1,3-diene, A, will react with cyclohexene when heated in a dark container overnight. However, no reaction will occur between buta-1,3-diene and cyclohexene if it is subjected to ultraviolet light during the reaction. Explain this behavior, using whatever molecular orbital (MO) diagrams you feel are necessary

3. The Diels-Alder reaction is quite useful in preparing cyclic or polycylic compounds from dienes. However, the rate that the reaction can occur at, as well as the stereochemistry of the product, can depend on the starting materials used. a) Buta-1,3-diene, A, participates in Diels-Alder reactions, but much more slowly that cyclopentadiene, B, while the compound 3-methylidenecyclohexene, C, does not react at all. Explain the difference in reactivity of these three dienes in Diels- Alder reactions. B C b) Buta-1,3-diene, A, will react with cyclohexene when heated in a dark container overnight. However, no reaction will occur between buta-1,3-diene and cyclohexene if it is subjected to ultraviolet light during the reaction. Explain this behavior, using whatever molecular orbital (MO) diagrams you feel are necessary

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter13: Substitution

Section: Chapter Questions

Problem 55CTQ

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Similar questions

This 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.
This 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.
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.
For the following dienes, identify whether the molecules has any cis or trans stereochemistry and idenfity the conformation as either s-cis or s-trans, where appropriate. Please also note whether the compound would be reactive in a Diels -Alder reaction
Draw 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).
Use MO diagram to determine which of the following reacts are symmetry allowed and which is symmetry forbidden. For reaction (a), assume that electrons flow from the diene to the dienophile.
Only one isomer of product is formed in the Diels-Alder cycloaddition. Why?
Give the structure(s) of the product(s) of each reaction. Indicate any relative stereochemistry, assuming that each of the Diels-Alder reactions will proceed with endo selectivity. If more than one product is formed, please indicate which one will be the major product or if they will be formed in equal amounts. If no reaction is expected to occur under the indicated conditions, then write "no reaction" or NR, and explain why you would expect nothing to occur. In all cases, equimolar amounts of both components/reagents are present unless indicated otherwise.
Draw a detailed mechanism and give the products for the following Diels-Alder reaction. Label the Endo and Exo diastereomer.
Consider a traditional Diels Alder reaction noting it's methodology and synthetic tactical. Then propose an alternative, greener synthetic route to make the same product with near or same enantioselectivity.
Expain the below Rule: The diene can react only when it adopts the s-cis conformation.
Rank the following dienes from most reactive to least reactive in a Diels Alder reaction. please explain steps