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Stereochemistry

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Stereochemistry Stereochemistry refers to the 3-dimensional properties and reactions of molecules. It has its own language and terms that need to be learned in order ... – PowerPoint PPT presentation

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Title: Stereochemistry


1
Stereochemistry
  • Stereochemistry refers to the
  • 3-dimensional properties and reactions of
    molecules. It has its own language and terms
    that need to be learned in order to fully
    communicate and understand the concepts.

2
Definitions
  • Constitutional Isomers- compounds with same
    atoms, different connectivity
  • Stereoisomers compounds with the same
    connectivity, different arrangement in space
  • Enantiomers stereoisomers that are
    non- superimposible mirror images only
    properties that differ are direction ( or -)
    of optical rotation
  • Diastereomers stereoisomers that are not
    mirror images different compounds with
    different physical properties

3
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4
More Definitions
  • Asymmetric center sp3 carbon with 4 different
    groups attached
  • Optical activity the ability to rotate the
    plane of plane polarized light
  • Chiral compound a compound that is optically
    active (achiral compound will not rotate light)
  • Polarimeter device that measures the optical
    rotation of the chiral compound

5
Plane-Polarized Light

6
Plane-Polarized Light through an Achiral Compound
7
Plane-Polarized Light through a Chiral Compound
8
Polarimeter Measures Optical Rotation
9
Specific Rotation, a
  • a a / cl
  • a observed rotation
  • c concentration in g/mL
  • l length of tube in dm
  • Dextrorotary designated as d or (), clockwise
    rotation Levorotary designated as l or (-),
    counter- clockwise rotation

10
Specific Rotations of some Common Organic
Compounds
  • Compound a centers
  • Penicillin V 233.0 3
  • Sucrose 66.5 10 
  • Camphor 44.3 2
  • MSG 25.5 1
  • Cholesterol -31.3 8
  • Morphine -132.0 5

11
Chirality CenterCarbon has four different groups
attached
12
Enantiomers nonsuperimposible mirror images
13
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14
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15
Biological Activity
16
SSRI Efficacy depends on Stereochemistry
17
Absolute Configuration
18
Assign Priority to each Group on Asymmetric Center
19
Lactic Acid
20
C.I.P. Priorities
21
Fischer Projections
22
Assigning Absolute Configuration to Fischer
Projections
23
Rotation of the Projection 90oReverses Absolute
Configuration
24
DiastereomersStereoisomers That Are Not Mirror
Images
25
Fischer Projections with 2 Chiral Centers
26
2 Chiral Centers4 Stereoisomers
27
Identical, Enantiomers or Diastereomers?
28
Tartaric Acids
29
Racemic Mixture
30
Meso CompoundInternal Plane of Symmetry
Optically Inactive
31
2,3,4-trichlorohexaneHow many stereoisomers?
32
n 3 2n 8
33
A Carbohydrate
34
Internal Planes of Symmetry
35
Asymmetric Centers on Rings
36
Reactions Bromination
37
Bromonium Ion is Opened Equally from Both Sides
38
Brominations Often Generate Asymmetric Centers
39
Asymmetric Center is Generated Racemic Mixture
Formed
40
Preparation of (L)-Dopafor Treatment of
Parkinsons
41
Relevance of Stereochemistry
42
One-step synthesis
43
a-(p-isobutylphenyl)propionic acid
44
Model of Thalidomide
45
How Sweet it is!
Sucralose is 600 times sweeter and does not get
metabolized.
46
Radiosensitizer of Choice Until 2004
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