s20 2011 week 1 day 4 - post-2

s20 2011 week 1 day 4 - post-2 - Chemistry S-20ab Week 1...

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Frontier Orbitals of Proton-Transfer Reactions We can, of course, look at proton-transfer reactions in terms of the HOMO and LUMO involved in the reaction. Can you find the HOMO and LUMO of the following proton- transfer reactions? OH + HCl OH 2 + Cl OH + H 3 CC C O + H 3 CH What generalization can we make about the LUMO in any proton-transfer reacton? Reading : Supplemental Handout, Section 2.6 Chemistry S-20ab Week 1 45
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What ! s Your Role: Acid or Electrophile? In one of the following reactions, acetone ((CH 3 ) 2 C=O) plays the role of an acid; in the other it plays the role of an electrophile. Which is which, and why? Can you draw the curved arrows and identify the HOMO and LUMO of each reaction? H 3 C CH 3 O H 3 C CH 3 O OH + HO H 3 C CH 3 O H 3 C CH 2 O + HO + H 2 O Reading : Supplemental Handout, Section 2.7 Chemistry S-20ab Week 1 46
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What ! s Your Role: Base or Nucleophile? In one of the following reactions, acetone ((CH 3 ) 2 C=O) plays the role of a base; in the other it plays the role of a nucleophile. Which is which, and why? Can you draw the curved arrows and identify the HOMO and LUMO of each reaction? H 3 C CH 3 O H 3 C CH 3 OH + H 3 O + + H 2 O H 3 C CH 3 O H 3 C CH 3 O CH 3 O CH 3 H 3 C CH 3 + O H 3 C CH 3 + Reading : Supplemental Handout, Section 2.7 Chemistry S-20ab Week 1 47
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Pop Quiz (don’t worry, this will not be graded!) For each of the following molecules: • Identify the HOMO • Identify the LUMO • Name the functional group O O H O Br O O O O C N Chemistry S-20ab Week 1 48
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s20 2011 week 1 day 4 - post-2 - Chemistry S-20ab Week 1...

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