Problem_set_5

Problem_set_5 - as illustrated and reside to the left? HO S...

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Problem set 5 ; Chem. 127/227 (fall quarter 2007) 1. (a) Draw accurate three dimensional representations for each structure shown below. (b) Your formulation for the structure shown on the left ought to clearly convey the idea that the two redox centers are close to one another. Given that proximity, it is not unreasonable to postulate the existence of an intramolecular “hole transfer” leading to the structure shown on the right. Illustrate that process. (Note: One can also think of the process as an intramolecular electron transfer; think of it that way if it helps.) (c) What information was given in class that makes one confident that the equilibrium will be
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Unformatted text preview: as illustrated and reside to the left? HO S S MeO OBn H HO S S MeO OBn H 2. Use the curly arrow formalism to illustrate the interconversion of each structure shown below. Note that the sequence that is portrayed accounts for the formation of the minor product in the reaction that was discussed in class. [Notice that overall, the oxidation involves the loss of two electrons and the equivalent of two protons. Conversely, many reductions involve the overall gain of two electrons and the equivalent of two protons.] HO S S MeO OBn H HO S MeO OBn H S HO MeO OBn H S S HO MeO OBn H S S HO MeO OBn H OMe H MeOH HO OMe MeO MeO OBn H a) H b) e c) MeOH d) H...
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