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Chapter 7 - Stereochemistry Enantiomers of bromochlorofluoromethane - - PowerPoint PPT Presentation
Chapter 7 - Stereochemistry Enantiomers of bromochlorofluoromethane - - PowerPoint PPT Presentation
Chapter 7 - Stereochemistry Enantiomers of bromochlorofluoromethane Non-superimposable mirror images Enantiomers Figure 7.1 7.12 Optically active molecules of biological importance O O O N OH N O N NH 2 O N H HO H codeine
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O O HO H N codeine O N N O strychnine HO H H H cholesterol NH2 N H O OH tryptophan NH2 HO HO L-dopa OH OH HO O HO O OH OH HO HO O sucrose
7.12 Optically active molecules of biological importance
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$100 billion sales worldwide in 2000 Account for 32% of the $360 billion total drug sales
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7.2 The Chirality Center
Carbon atom is asymmetric C is a stereogenic center Enantiomers are stereoisomers since the atoms at the stereogenic carbon are arranged differently in space.
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Mirror images of chlorodifluoromethane are superimposable Figure 7.2
Achiral i.e. not chiral
7.3 Symmetry in achiral structures
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7.4 Optical activity
Figure 7.4 Typical polarimeter setup : [α]D = 100 x (rotation)/(cell length) x (concentration)
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7.8 Enantiomers
same physical properties except rotation of plane polarized light
- ne enantiomer positive rotation (+) other negative rotation (-)
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Which molecules contain chiral (stereogenic) centers?
The stereogenic C must have 4 different groups attached
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7.5 Absolute and Relative Configuration
Absolute Configuration – Actual arrangement of substituents in space (+)-2-butanol and (-)-2-butanol, but which is which? Relative Configuration - Configuration relative to another compound. Pre-1951, compounds could be related to each other but the absolute configuration was not able to be determined.
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7.6 Nomenclature - Use of the Cahn-Ingold-Prelog System (R) and (S)
S enantiomer R enantiomer R - Rectus - the clockwise arrangement of groups S - Sinestre - the counterclockwise arrangement of groups
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7.6 Nomenclature - Use of the Cahn-Ingold-Prelog System
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7.7 Fischer projection formulas
Figure 7.5
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7.9 Reactions that create a Chirality Center
Figure 7.6
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7.10 Chiral molecules with two Chirality Centers
Figure 7.7
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7.10 Representations of (2R, 3R)-dihydroxybutanoic acid
Figure 7.8
All the same molecule: (a) and (b) differ only by bond rotation (b) leads to correct Fischer projection Conversion of “zig-zag” picture to Fischer projection
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7.10 Chiral molecules with two Chirality Centers
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7.11 Achiral molecules with two Chirality Centers
Figure 7.9
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Meso-2,3-butanediol
Figure 7.10
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7.12 Stereogenic centers in cholic acid
Figure 7.11
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O O HO H N codeine O N N O strychnine HO H H H cholesterol NH2 N H O OH tryptophan NH2 HO HO L-dopa OH OH HO O HO O OH OH HO HO O sucrose
7.12 Optically active molecules of biological importance
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7.13 Reactions that produce diastereomers
Figure 7.12
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7.14 Resolution of a chiral substance into its enantiomers
Figure 7.13
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