6-StereochemistryF07 - Hands on Handedness Stereochemistry...

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1 Hands on Handedness – Stereochemistry with Molecular Models Reading assignment: Review chapter 6 in Loudon. Pay special attention to sections 6.1, 6.3, 6.4, 6.6 and 6.8. 2-bromobutane. One partner should build 2-bromobutane. The other partner should build the mirror image. 1) Complete the drawings ( 1 and 1’ ) below to represent the models you have built. Partner 1 Partner 2 C H C H H H 3 C H CH 3 mirror 1 2 1' 2' 2) Identify all asymmetric carbons with an asterisk (*). 3) Pick up each of the models and look down the asymmetric carbon – hydrogen bond and complete the drawings 2 and 2’ . Assign R or S configuration to each . 4) Does either molecule possess an internal plane of symmetry? 5) Is it possible to superimpose the first model on the second? 6) Each molecule is: chiral or achiral (Circle your answer) 7) What is the relationship between the two molecules? Enantiomers Diastereomers Constitutional Isomers Identical 8) What can you conclude about the configuration of the asymmetric carbons of enantiomers: Same Opposite Not related 9) Imagine the molecule (2S, 3R, 4R, 5S)-bigfella. Complete the configuration of the enantiomer of bigfella: (2 , 3 , 4 , 5 ) – bigfella. 10) What is required to convert one molecule into the other so that they are the same (superimposable – point by point)? a) Rotate around σ -bond b)Break σ -bond to two groups and interchange c) Change order in which atoms are bound d)Add atoms
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2 11) Arrange one of the models so that it is in conformation A. Is this the R or S enantiomer? CH
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This note was uploaded on 05/13/2010 for the course CHEM 151L taught by Professor Roy,christopher during the Fall '08 term at Duke.

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6-StereochemistryF07 - Hands on Handedness Stereochemistry...

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