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ps10 - CH 3 H 3 C CH 3 BF 3-OEt 2 diethyl ether(solvent H 3...

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Chemistry 3590 Honors Organic Chemistry I PROBLEM SET #10 FALL, 2009 Please answer problems 47, 51, 52, 55, 69, 73 and 80 in Chapter 10 of Bruice, as well as the following questions: (1) When the epoxide 1 shown below was treated with the Lewis acid boron trifluoride etherate, the product 2 was formed in good yield. Using the curved arrow formalism, draw a reaction mechanism for this process.
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Unformatted text preview: CH 3 H 3 C CH 3 BF 3-OEt 2 diethyl ether (solvent) H 3 C CH 3 H 3 C OH H O H H 1 2 (2) Using (E)-3-methyl-2-pentene, devise separate synthetic routes to the compounds 3 and 4 shown below. Note that each of these structures is a racemic mixture of a single diastereomer. Your syntheses should not produce mixtures. CH 3 HO CH 3 CH 2 H 3 CO H CH 3 CH 3 CH 3 CH 2 H 3 CO H OH CH 3 3 4...
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