PQ-21. From the standpoint of reactivity, which is the poorest dienophile to react with2,3-dimethyl-1,3-butadiene in a Diels-Alder reaction?H(A)CO2CH3(B)(C)(D)CN

It is an example for (4+2) cyclo addition reaction 4pi electron species are dienes, 2pi electron…

Answered: From the standpoint of reactivity,…

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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

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

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PQ-21. From the standpoint of reactivity, which is the poorest dienophile to react with
2,3-dimethyl-1,3-butadiene in a Diels-Alder reaction?
H
(A)
CO2CH3
(B)
(C)
(D)
CN

Expert Solution

Step 1 Diels Alder reaction

It is an example for (4+2) cyclo addition reaction
4pi electron species are dienes, 2pi electron species are dienophiles
2 C-C bonds , 1 C=C bond formation takes place in this reaction
Thermally allowed reaction
HOMO orbital of diene, LUMO of dienophile takespart in this reaction
Only S-cis dienes are involved in this reaction, in S-trans dienes no cyclisation
It is a stereo specific reaction with respect to the dienophile, Cis-dienophile gives cis-adduct and trans dienophile gives trans-adduct
Electron releasing group containing dienes are more reactive in this reaction, because HOMO orbitals are involved
Electron with drwaing dienophiles are more reactive in Diels-Alder reaction, since LUMO orbitals are involved.

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