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Would you expect nitroethylene to be more or less reactive

Chapter 17, Problem 17.64

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QUESTION:

Would you expect nitroethylene to be more or less reactive than ethylene in a Diels-Alder reaction? (Hint: Draw the resonance structures of nitroethylene.) Ethylene Nitroethylene N O O ! @

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QUESTION:

Would you expect nitroethylene to be more or less reactive than ethylene in a Diels-Alder reaction? (Hint: Draw the resonance structures of nitroethylene.) Ethylene Nitroethylene N O O ! @

ANSWER:

Step 1 of 2

Recall that in a Diels-Alder reaction, we find that electron withdrawing groups (such as the nitro group) on the dienophile make the overall reaction go faster. This is a result of the LUMO of the dienophile being the accepter for the diene electrons;  electron withdrawing groups facilitate this process.

 

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