Ch 5 - Aromatic Compounds - 3 Biosynthesis of Lysergic acid...

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Representative Compounds HO OH CHCH 2 NHCH 3 OH adrenaline ephedrine CHCHNHCH 3 OH CH 3 amphetamine CH 2 CHNH 2 CH 3 methamphetamine CH 2 CHNHCH 3 CH 3 speed
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All aromatic compounds are: - planar (and cyclic) - have one p orbital on each atom of the ring - have 6 (10, 14 etc.) pi electrons: follow 4n + 2 electron rule - each atom of the the ring is sp 2 hybridized
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Which of the following compounds is aromatic? N H 1. 2. 3. 4.
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Which are aromatic? sp
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Unformatted text preview: 3 Biosynthesis of Lysergic acid N H NMe H HO O N H NMe H N O Lysergic acid Lysergic acid diethylamide (LSD) Biosynthesis of morphine MeO O O N Me H Electrophilic Aromatic Substitution : replace H on ring with a substituent 1. make an electrophile (something with a + charge) 2. break the aromatic ring = resonance stabilized carbocation 3. restore the aromatic ring...
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This note was uploaded on 03/01/2010 for the course CHEM 1570 taught by Professor Usher, d during the Spring '08 term at Cornell University (Engineering School).

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Ch 5 - Aromatic Compounds - 3 Biosynthesis of Lysergic acid...

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