Chem241a_Lecture_24

Chem241a_Lecture_24 - Organic Ch emistry 241a Prof Bogdan...

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Unformatted text preview: Organic Ch emistry 241a Prof. Bogdan Olenyuk Contact Information Office: Old Chemistry 309 [email protected] Phone: (520) 626-0754 Course web site: http://www.chem.arizona.edu/courseweb/074/CHEM241A1_2/FrameSet.html Chapter 9: Stereochemistry • IUPAC sequence rules for specification of configuration • Diastereomers • Meso compounds • Stereochemistry of reactions • Prochirality • Chirality in nature Today we will cover: Reading Assignment: McMurry (the BOOK), Ch. 9.5-9.14 Sequence Rules (IUPAC) Rule 1: • Assign each group priority according to the Cahn Ingold-Prelog scheme • With the lowest priority group pointing away, look at remaining 3 groups in a plane • Clockwise is designated R (from Latin for “right”) • Counterclockwise is designated S (from Latin word for “left”) Rule 2: • If decision can’t be reached by ranking the first atoms in the substituents, look at the second, third, or fourth atoms until difference is found Rule 3: • Multiple-bonded atoms are equivalent to the same number of single-bonded atoms Diastereomers • Molecules with more than one chirality center have mirror image stereoisomers that are enantiomers • In addition they can have stereoisomeric forms that are not mirror images, called diastereomers Meso Compounds...
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This note was uploaded on 08/23/2008 for the course CHEM 241A taught by Professor Olenyuk during the Fall '07 term at Arizona.

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Chem241a_Lecture_24 - Organic Ch emistry 241a Prof Bogdan...

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