Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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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
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Transcribed Image Text: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
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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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