lecture 16 given - Lecture 16 Organic Chemistry I Prof....

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Organic Chemistry I 310/318M Pre-Health Professionals Unique numbers: 54410, 54435, 54440, 54445, and 54655 Prof. Jonathan L. Sessler Lecture 16 Notes: Homework 4 due Wednesday. Dr. Sessler’s Office Hours (in his office, Wel 5.428) will end at 2 pm today. Exams will be ready for pick up in the undergraduate office by late afternoon.
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π - Electrons As Basic Sites Proton-transfer reactions occur with compounds having pi electrons, as for example the π -electrons of carbon-carbon double and triple bonds. ± The π - electrons of 2-butene, for example, react with HBr by proton transfer to form a new C-H bond. ± The result is formation of a carbocation carbocation , a species in which one of its carbons has only six electrons in its valence shell and carries a charge of +1. As shown in class, it reacts with Br - . CH 3 -CH=CH-CH 3 + H -Br 3 -C-C-CH 3 H H + 2-Butene sec- Butyl cation (a 2?carbocation) H Br
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π - Electrons As Basic Sites Problem 4.4 Problem 4.4 Draw Lewis structures for the two possible carbocations formed by proton transfer from HBr to 2-methyl-2- butene. CH 3 -C=CH-CH 3 + H-Br 2-Methyl-2-butene 3 We can use this problem to learn already that more highly substituted carbocations are more stable.
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lecture 16 given - Lecture 16 Organic Chemistry I Prof....

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