DielsAlder reaction of a monosubstituted diene (such as CH2 CH CH CHOCH3) with a

Chapter 16, Problem 16.55

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DielsAlder 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 1,2-disubstituted product major CHO CHO OCH3 1,3-disubstituted product minor CHO OCH3 +

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