ps5 - form achiral or racemic products” was first...

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Chemistry 3590 Organic Chemistry I PROBLEM SET #5 FALL, 2008 Please answer problems 61, 63, 66, 74, 84 and 92 in Chapter 5 of Bruice, and the following questions: (1) Two stereoisomers of the compound (NH 3 ) 2 PtCl 2 are known, and they have different physical properties. What does this fact say about the possibility of either tetrahedral or square planar arrangements of the groups around Pt? (2) What simple reaction of an alkene could be used to convert ( S )-3-fluorocyclohexene to a single product that is achiral? Show the reaction and the expected product. (3) Which of the bromochlorocyclohexanes A-E below are enantiomers? Which, if any, is/are achiral compounds? Cl Br Cl Br Cl Br Br Cl Br Cl A B C D E (4) The concept that without using chiral reagents or techniques, “achiral or racemic reactants can only
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Unformatted text preview: form achiral or racemic products” was first articulated by Louis Pasteur. An apple is an achiral object, which can be cut with a knife (also an achiral object) in the following way: Imagine cutting the apple halfway through from the north pole (i.e. where the stem is), then halfway through from the south pole (i.e. the bottom) so that the two cuts are perpendicular to one another. Then make two quarter-cuts in opposite quadrants to complete the dissection, which should give two pieces like those shown below. What is the relationship (in terms of chirality) of the two half-apples? What are the ramifications for Pasteur’s hypothesis?...
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This note was uploaded on 11/10/2009 for the course CHEM 1570-001 taught by Professor Tadhgbegley during the Fall '08 term at Cornell.

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