7. Diels-Alder reactions are not limited to dienes and dienophiles with only carbon atoms like we have seen in lecture. Other atoms (heteroatoms) can be included in the system of the diene and/or the dienophile. The following are examples of hetero Diels-Alder reactions. Draw the mechanism and predict the product of both reactions, paying particular attention to stereochemistry. H O MeO₂C + CO₂Me +

7. Diels-Alder reactions are not limited to dienes and dienophiles with only carbon atoms like we have seen in lecture. Other atoms (heteroatoms) can be included in the system of the diene and/or the dienophile. The following are examples of hetero Diels-Alder reactions. Draw the mechanism and predict the product of both reactions, paying particular attention to stereochemistry. H O MeO₂C + CO₂Me +

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

Section14.SE: Something Extra

Problem 41AP: Although the Dielsâ€“Alder reaction generally occurs between an electronrich diene and an...

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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?
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).
Rank the following dienes from most reactive to least reactive in a Diels Alder reaction. please explain steps
Although the Dielsâ€“Alder reaction generally occurs between an electronrich diene and an electron-deficient dienophile, it is also possible to have inverse-demand Dielsâ€“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 Dielsâ€“Alder reaction below. Be sure your products reflect the correct stereochemistry. If more than one regioisomer is possible, draw both.
Rank the following dienes from most to least reactive in a Diels-Alder reaction. Provide an explanation for each ranking. Draw a mechanism and show the product for the following reaction, paying close attention to stereochemistry.
Diels–Alder reaction of a monosubstituted diene (such as CH2=CH– CH=CHOCH3) with a monosubstituted dienophile (such as CH2=CHCHO) gives a mixture of products, but the 1,2-disubstituted product often predominates. Draw the resonance hybrid for each reactant, and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.
Diels—Alder reaction of a monosubstituted diene (such as CH2 = CH – CH = CHOCH3) with a monosubstituted dienophile (such as CH2 = CHCHO) gives a mixture of products, but the 1,2-disubstituted product often predominates. Draw the resonance hybrid for each reactant and use the charge distribution of the hybrids to explain why the 1,2-disubstituted product is the major product.
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.
Rank the following dienes in their rate of reaction with the same dienophile in a Diels-Alder reaction. For example, 1 = fastest or most reactive diene, 4 = slowest or least reactive diene.
This 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.
In 4+2 cycloaddition, ENDO stereochemistry is preferred because: endo stereochemistry allows the diene to adopt s-cis conformation. endo stereochemistry results in less steric hindrance. the transition state leading to endo stereochemistry is higher energy. it allows for additional π to π overlap between the diene and the dienophile.
Rank the following dienes from most reactive to least reactive in a Diels–Alder reaction: