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ProblemSet11 - CHEM 3570 FALL 2009 Problem Set 11 1 The...

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CHEM 3570, FALL 2009 Problem Set 11 1) The following ether can be assembled using two DIFFERENT Williamson ether synthetic approaches. a) Show the starting materials needed for each of these approaches. b) Circle the Williamson ether synthetic approach that would work better in the lab. O 2) An Icelandic foreign exchange student is planning to execute the following synthetic sequence. Would you advice him against running these experiments? What is wrong, if anything? He still needs to make this product from the starting material shown, could you help him out by suggesting an alternative route. OH Br 1) Mg 2) O OH OH NaH, CH 3 I OCH 3 OCH 3 3) Design a synthesis of 3-ethyl-2-methyl-3-hexanol from propene as the exclusive source of carbon. All reagents are available.
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