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0243Pb25-09 - and solid wedges to represent bonds coming...

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Problem 25, Chem 0243, 2009 Serricornin, the female-produced sex pheromone of the cigarette beetle, whatever that is, has the following schematic structure. O OH (a) Point out with an * the stereogenic carbons (b) What is the maximum number of possible stereoisomers? (c) Draw the S configuration at each stereogenic carbon (the natural configuration). It is best to adopt a convention to do this. Use dashed wedges to represent retreating bonds
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Unformatted text preview: and solid wedges to represent bonds coming forward. For example, one might write A to represent the S,S,S isomer, but, as a former US president once said, “That would be wrong.” In fact, if you can decipher the R/S stereochemistry of A , you should be able to short-cut the construction of the SSS isomer. A O OH...
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