Lecture 16 - (1) . The atom with the lowest atomic number...

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Reading Assignment : Sections 4.1-4.3 CH 310M/318M – MWF 12pm – Lecture 16 – F 10/3/2008 Graded Homework : HW#08 deadline = 3:00 p.m. on Mon 10/6 HW#09 deadline = 3:00 p.m. on Thu 10/9 If you have not yet picked up your graded exam, you will need to fill out an “Exam Request Form” and turn it in at WEL 2.212. Your exam will be available at the window the next business day. The deadline to submit all Midterm Exam #1 regrade requests is Tues., 10/7 @ 3:00 p.m. Last Time : Stereochemistry (continued…) Textbook Problems : 3.4-3.8, 3.10(a), 3.25-3.28, 3.30-3.32, 3.34, 3.36, 3.37 Today : Stereochemistry (continued…)
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Assigning R , S Stereochemical Designations This system is based on the Cahn–Ingold–Prelog priority rules. These rules are used to assign relative priorities to the four different groups attached to a chiral center. 1) Looking at the atoms directly attached to the chiral center, assign priorities in order of decreasing atomic number . The atom with the highest atomic number is ranked first
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Unformatted text preview: (1) . The atom with the lowest atomic number is ranked fourth (4) . 2) If a decision about priority cant be reached by applying rule 1, continue moving away from the chiral center, and compare atomic numbers of the second grouping of atoms. Continue on as necessary, always moving away from the chiral center, until the first point of difference is reached. 3) Multiply-bonded atoms are considered as if they were an equivalent number of singly-bonded atoms. 4) Once priorities have been assigned, the molecule is oriented so that the lowest priority group (4) points directly away from you. Then, observe how the other 3 groups are arranged around a circle. In effect, draw a Newman projection looking down the bond between the stereocenter and the group of priority (4) If moving from 1 2 3 is a clockwise movement, the configuration is R . If moving from 1 2 3 is a counterclockwise movement, the configuration is S ....
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This note was uploaded on 01/20/2010 for the course CH 310M taught by Professor Iverson during the Fall '05 term at University of Texas at Austin.

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Lecture 16 - (1) . The atom with the lowest atomic number...

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