Lecture10CHM233(10)final

Lecture10CHM233(10)final - Organic Chemistry, Third Edition...

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1 Organic Chemistry, Third Edition Janice Gorzynski Smith University of Hawai’i Chapter 5
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Which drawing shows the stereogenic centers of menthol? OH OH OH OH OH OH * * * * * * * * * * * * * * * A B C D E menthol !
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How many stereogenic centers does the molecule of cholesterol have? A. 9 B. 4 C. 8 D. 5 E. 6 HO CH 3 CH 3 H H H Cholesterol !
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4 Some Biologically Active Molecules with Stereogenic Centers on Rings
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5 Since enantiomers are two different compounds, they need to be distinguished by name. This is done by adding the prefix R or S to the IUPAC name of the enantiomer. To designate enantiomers as R or S , priorities must be assigned to each group bonded to the stereogenic center, in order of decreasing atomic number. The atom of highest atomic number gets the highest priority (1). Labeling Stereogenic Centers with R or S
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6 If two atoms on a stereogenic center are the same, assign priority based on the atomic number of the atoms bonded to these atoms. One atom of higher atomic number determines the higher priority. Assigning Priority for R and S
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7 If two isotopes are bonded to the stereogenic center, assign priorities in order of decreasing mass number. Thus, in comparing the three isotopes of hydrogen, the order of priorities is: Assigning Priority for R and S –Isotopes
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8 To assign a priority to an atom that is part of a multiple bond, treat a multiple bonded atom as an equivalent number of singly bonded atoms.
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This note was uploaded on 01/03/2012 for the course CHEM 233 taught by Professor Anamoore during the Fall '10 term at ASU.

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Lecture10CHM233(10)final - Organic Chemistry, Third Edition...

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