7. Although the Diels-Alder reaction generally occurs between an electron-rich diene and an electron- deficient dienophile, it is also possible to have inverse-demand Diels-Alder reactions between suitable electron-deficient 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 regio-isomer is possible, draw both.

7. Although the Diels-Alder reaction generally occurs between an electron-rich diene and an electron- deficient dienophile, it is also possible to have inverse-demand Diels-Alder reactions between suitable electron-deficient 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 regio-isomer is possible, draw both.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

Reactions of Ethers

Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.

Epoxides

Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.

Williamson Ether Synthesis

An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.

Question

**Educational Content on Inverse-Demand Diels–Alder Reactions**

**Problem 7: Inverse-Demand Diels–Alder Reactions**

Although the Diels–Alder reaction generally occurs between an electron-rich diene and an electron-deficient dienophile, it is also possible to have inverse-demand Diels–Alder reactions between suitable electron-deficient 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 regio-isomer is possible, draw both.

**(a)**
- Reactants:
- Diene: 1,1,2,3,4-pentachloro-1,3-butadiene
- Dienophile: An electron-rich alkene containing a CH₂O group.

**(b)**
- Reactants:
- Diene: An electron-deficient diene featuring a carbonyl group (oxo group).
- Dienophile: An alkene structured as a six-membered cyclohexene.

**(c)**
- Reactants:
- Diene: An unsaturated methyl ester with the formula C4H6O2.
- Dienophile: An ethyl vinyl ether with the formula C3H6O.

**Instructions:**
- Predict the products reflecting correct stereochemistry.
- If more than one regio-isomer is possible, draw both.

Note: The diagrams provided depict the structures of each diene and dienophile for clarity in predicting the reaction outcomes.

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