OCH3 OCH3 CHO A OCH, CHO CHO 1,2-disubstituted product 1,3-disubstituted product major minor

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 26MP: Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium...
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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.

 

OCH3
OCH3
CHO
A
OCH,
CHO
CHO
1,2-disubstituted product
1,3-disubstituted product
major
minor
Transcribed Image Text:OCH3 OCH3 CHO A OCH, CHO CHO 1,2-disubstituted product 1,3-disubstituted product major minor
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