10142009 - C H H 3 C NH 2(R(R C C O OH CH 3 H HO Lactic...

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CH 310M/318M – MWF 12:00 – Lecture 21 – W 10/14/2009 Reading Assignment : Section 5.3 (last book material for Exam #2) Graded Homework : HW#11 deadline = 3:00 p.m. on Thu 10/15 HW#12 deadline = 3:00 p.m. on Mon 10/19 Textbook Problems : Catch up on Chapter 4 problems!!! Last Time : Acid-base equilibria (continued…) Structural factors that influence acid/base strength Today : Structural factors that influence acid/base strength (continued…) Acid-base chemistry in the resolution of enantiomers Interested in a study abroad experience??? Information about the Summer 2010 “Organic Chemistry in Spain” program will be held in WCH 1.110 at the following times: Wednesday, 10/14 @ 5:00 p.m. Tuesday, 10/20 @ 5:00 p.m. Tuesday, 11/3 @ 5:00 p.m.
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C H H 3 C NH 2 (R) (R) C C O OH CH 3 H HO Lactic acid
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Unformatted text preview: C H H 3 C NH 2 (R) (R) C C O OH CH 3 H HO Lactic acid (R)-(50%) C C O O CH 3 H HO C H H 3 C NH 3 Acid-Base Chemistry in the Resolution of Enantiomers The process of separating a racemic mixture into its component enantiomers is called resolution . In practice, the resolution of enantiomers can be difficult, because of the fact that enantiomers have identical physical properties. (optically active) (R)-1-phenylethylamine (chiral) + Relationship? diastereomeric salts Diastereomers typically differ in their physical properties, and thus are more easily separable (separable) C CH 3 H HO C O OH Lactic acid (S)-(50%) + (not separable) C CH 3 H HO C O O (R) C H H 3 C NH 3 (S) (optically inactive) (optically active)...
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