Lecture9CHM233(10)final

Lecture9CHM233(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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2 Stereochemistry Stereochemistry refers to the three-dimensional structure of a molecule. As a consequence of stereochemistry, apparently minor differences in 3-D structure can result in vastly different properties. We can observe this by considering starch and cellulose , which are both composed of the same repeating unit.
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3 Stereochemistry of Starch and Cellulose In cellulose, the O atom joins two rings using equatorial bonds. In starch, the O atom joins two rings using one equatorial and one axial bond. Due to these differences in stereochemistry, humans can metabolize starch for energy but we cannot digest cellulose.
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Figure 5.1
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5 Figure 5.2 3-D Structure of Starch and Cellulose
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Isomers Nonidentical compounds having the same molecular formula
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7 Constitutional Isomers Isomers are different compounds with the same molecular formula Constitutional/structural isomers have: different IUPAC names same or different functional groups different physical properties different chemical properties
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8 Stereoisomers Differ only in the way the atoms are oriented in space. Have identical IUPAC names (except for a prefix like cis or trans ). Always have the same functional group(s). Differ in configuration (its particular three- dimensional arrangement).
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9 Constitutional and Stereoisomers Figure 5.3
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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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Lecture9CHM233(10)final - Organic Chemistry, Third Edition...

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