MWF_11 - Organic Lecture Series CH 310/318 M Textbook...

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Organic Lecture Series 1 CH 310/318 M LECTURE 11 Textbook Assignment: Chapter 4 Today’s Topics: Acid Base Chemistry Acid Base Chemistry -Introduction; Introduction; pKa pKa Notice & Announcements: Health Professions Seminar, 2/10: WEL 1.316; 2-3 pm Karen Cohen, MD Radiation Oncologist Mary Gonzalez, MD Physical Medicine and Rehabilitation Garrett Scales, MD Anesthesiologist Organic Lecture Series 2 Acids and Acids and Bases Bases Chapter 4 Chapter 4
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Organic Lecture Series 3 • Many organic molecules have two or more sites that can act as proton acceptors. ¾ In this chapter, discussion is limited to carboxylic acids, esters, and amides. ¾ In these molecules, the favored site of protonation is the one in which the charge is more delocalized. ¾ Question: Which oxygen of a carboxylic acid is protonated? CH 3 -C-O-H O + H 2 SO 4 CH 3 H O + +HSO 4 - or CH 3 H O + A (protonated on the carbonyl oxygen) B (protonated on the hydroxyl oxygen) Resonance in Acids Resonance in Acids Organic Lecture Series 4 π Electrons As Basic Sites Electrons As Basic Sites Proton-transfer reactions occur with compounds having π electrons, as for example the π electrons of carbon- carbon double and triple bonds. The pi electrons of 2-butene, for example, react with HBr by proton transfer to form a new C-H bond. 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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Organic Lecture Series 5 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.
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MWF_11 - Organic Lecture Series CH 310/318 M Textbook...

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