Chapter 7 - Stereochemistry Enantiomers of bromochlorofluoromethane Non-superimposable mirror images – Enantiomers.

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Presentation transcript:

Chapter 7 - Stereochemistry Enantiomers of bromochlorofluoromethane Non-superimposable mirror images – Enantiomers

Figure 7.1YSU

7.12 Optically active molecules of biological importanceYSU

$100 billion sales worldwide in 2000 Account for 32% of the $360 billion total drug salesYSU

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.YSU

Mirror images of chlorodifluoromethane are superimposable Figure 7.2 Achiral i.e. not chiral 7.3 Symmetry in achiral structuresYSU

7.4 Optical activity Figure 7.4 Typical polarimeter setup : [  ] D = 100 x (rotation)/(cell length) x (concentration)YSU

7.8 Enantiomers same physical properties except rotation of plane polarized light one enantiomer positive rotation (+) other negative rotation (-)YSU

Which molecules contain chiral (stereogenic) centers? The stereogenic C must have 4 different groups attachedYSU

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.YSU

7.6 Nomenclature - Use of the Cahn-Ingold-Prelog System R enantiomerS enantiomer R - Rectus - the clockwise arrangement of groups S - Sinestre - the counterclockwise arrangement of groupsYSU (R) and (S)

7.6 Nomenclature - Use of the Cahn-Ingold-Prelog SystemYSU

7.7 Fischer projection formulas Figure 7.5 YSU

7.9 Reactions that create a Chirality Center Figure 7.6 YSU

7.10 Chiral molecules with two Chirality Centers Figure 7.7 YSU

7.10 Representations of (2R, 3R)-dihydroxybutanoic acid 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 Figure 7.8YSU

7.10 Chiral molecules with two Chirality CentersYSU

7.11 Achiral molecules with two Chirality Centers Figure 7.9YSU

Meso-2,3-butanediol Figure 7.10 YSU

7.12 Stereogenic centers in cholic acid Figure 7.11YSU

7.12 Optically active molecules of biological importanceYSU

7.13 Reactions that produce diastereomers Figure 7.12YSU

7.13 Reactions that produce diastereomers Figure 7.12YSU

7.14 Resolution of a chiral substance into its enantiomers Figure 7.13YSU

Not covering 7.15 and 7.16 YSU