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7. When 1-3 cyclopentadiene is treated with HBr, the temperature does not have an influence on the identity of the major product. Explain

7. When 1-3 cyclopentadiene is treated with HBr, the temperature does not have an influence on the identity of the major product. Explain

Chemistry
Chemistry
10th Edition
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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7. When 1-3 cyclopentadiene is treated with HBr, the temperature does not have an influence on the identity of the major product. Explain Diels-Alder Retro Diels-Alder (high temperature) A Diels-Alder reaction will procced more rapidly and with a much higher yield when the dieno- phile has an clectron-withdrawing substituent such as a carbonyl group: о H. 100% The carbonyl group is electron withdrawing because of resonance. Can you draw the reso- nance structures? Other examples of dieno- philes that possess clectron-withdrawing sub- stituents are shown here: CN OR HO. When the dienophile is a 1,2-disubstituted alkene, the reaction proceeds with stereospecificity. Specifically, stituted ring. a cis alkene produces a cis disubstituted ring, and a trans alkene produces a trans disub- + En > "X A triple bond can also function as a dienophile, in which case the product is a ring with two double bonds (a 1,4-cyclohexadicne). LOR OR OR
Transcribed Image Text:7. When 1-3 cyclopentadiene is treated with HBr, the temperature does not have an influence on the identity of the major product. Explain Diels-Alder Retro Diels-Alder (high temperature) A Diels-Alder reaction will procced more rapidly and with a much higher yield when the dieno- phile has an clectron-withdrawing substituent such as a carbonyl group: о H. 100% The carbonyl group is electron withdrawing because of resonance. Can you draw the reso- nance structures? Other examples of dieno- philes that possess clectron-withdrawing sub- stituents are shown here: CN OR HO. When the dienophile is a 1,2-disubstituted alkene, the reaction proceeds with stereospecificity. Specifically, stituted ring. a cis alkene produces a cis disubstituted ring, and a trans alkene produces a trans disub- + En > "X A triple bond can also function as a dienophile, in which case the product is a ring with two double bonds (a 1,4-cyclohexadicne). LOR OR OR
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