Ochem2 - . Your name Your 10 # . . Chemistry 1088 First...

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... Your name . Your 10 # . Chemistry 1088 First Midterm August 5 version 1 \ S.tM-1 f(O(/~ (Q ?- vJ/ b _ 1 Problem score 1 (30p) 2 (20p) 3 (10p) 4 (17p) 5 (15p) 6 (15p) 7 (10p) 8 (13p) total (130p) percentaae
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2 Problem 7 (30 points; 3 points each) In the following reactions either the product or the reagent (but not both) is missing. Complete them. In some cases more than one reagent may be needed. Do not show mechanisms. o 6 o 6 o if 1) CH s Mg Br Ag {NHs)2+ OH 6 OH 6 ~ OH o H ~O o II R-C-O-O- H ~ o OH ~O Continues on the next page
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3 H ~H ~ o 0 OH 0 ~CH3 ~CH3 pH4-6 ""-/NH- CH3
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4 Problem Z (20 points; 10 points each part) a) How would you carry out the following transformation. More than one step is needed. Do not show mechanisms. b) How would you carry out the following transformation. More than one step is needed. Show the mechanism for the last step of the synthesis indicating how the -Br and -OH group end up trans to each other. CH(Y~r .' OH (plus its enantiomer)
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5 Problem 3 (10 points) Give a detailed mechanism (arrow pushing) that explains the following reaction: OH h Problem 4 ( 17 points) One of the following ethers cannot be prepared by the Williamson ether synthesis. Circle it. (5 points) For the other two ethers, indicate the alcohol and the alkyl halide that you would use to make them by the Williamson synthesis. (12 points)
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6 Problem 5 (15 points) You have benzyl alcohol and cyclopentanone at your disposal. How would you prepare the compound shown below (target molecule) using these two starting materials and a Wittig
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Ochem2 - . Your name Your 10 # . . Chemistry 1088 First...

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