CHEM301 F10 CA7

CHEM301 F10 CA7 - CHEM301, Fall 2010 Dr. Ruder Class...

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CHEM301, Fall 2010 Dr. Ruder Class Activity 7 Stereochemistry Stereoisomers differ only by the spatial orientation of the atoms. Model 1: Stereoisomers of Thalidomide Thalidomide was originally prescribed for treatment of nausea and morning sickness in pregnant women. Unfortunately, thalidomide caused serious birth defects resulting in children born deaf, blind and with malformed limbs. One of the compounds shown below is thalidomide. N O O NH O O N O O NH O O A B C 13 H 10 N 2 O 4 C 13 H 10 N 2 O 4 Definitions of key terms: Stereoisomers - have the same atom connectivity but cannot be interconverted by rotation around single bonds and differ only in the three dimensional arrangement of atoms in space. Chirality center (stereogenic center) - carbon with four different groups Chiral compound – has chiral center and no plane of symmetry; the mirror image is not the same as the original Achiral compound – has plane of symmetry; the mirror image is the same as the original Enantiomers - non superimposable mirror images Questions: Consider the compounds A and B in Model 1 when answering the following questions. 1. Do the compounds have the same molecular formula? 2. Are A and B identical, constitutional or conformational isomers? Explain why. 3. Put an asterisk next to any carbon(s) that have four different substituents in both A and B. What term is used to identify this type of carbon (see list of terms)?
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CHEM301 F10 CA7 - CHEM301, Fall 2010 Dr. Ruder Class...

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