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.

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 Diels–Alder reaction generally occurs between an electronrich diene and an...
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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.
la)
CI
CI
Cl
CH2
CI
(b)
H2C
(c)
H2C
CO2CH3
H2C
OCH3
-
nth of maximum
Transcribed Image Text: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. la) CI CI Cl CH2 CI (b) H2C (c) H2C CO2CH3 H2C OCH3 - nth of maximum
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