f05efk - I(43 points Name Page 1 F.05.215FEP1 Complete the...

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Name _______________________ Page 1 F.05.215FEP1 I. (43 points) Complete the following reaction schemes as necessary. Sequential experimental steps should be numbered appropriately! Complete structures should be shown. N C O H CH 3 C O OCH 3 N MgBr (a) JOC 2005 70 9077 1) 2) H 3 O The product of this reaction is (check one): a single, achiral compound a racemic mixture a mixture of diastereomers (b) OL 2005 7 5163 N O HO CH 3 OH the sole product (with no by-products) resulting from the nucleophilic opening of a lactone (c) JOC 2005 70 8693 NH 3 O O OCH 3 OCH 3 N O O OCH 3 OCH 3 CH 3 H O O CH 2 Ph N O O OCH 3 OCH 3 CH 3 H O O CH 2 Ph (d) ibid 1) NaH 2) CH 3 I (e) JOC 2005 70 8687 O OH HO HO OH OH 1) H 3 C C O O C O CH 3 excess 2) HCl / acetic acid in pyridine draw the expected major anomer 6 5 6 6 8 6 6 1 equiv. C 17 H 16 N 2 O 3 N C HO H CH 3 C O OCH 3 N O O N H HO CH 3 1) CH 3 OH/TsOH 2) O O CH 2 Ph Cl N O O OCH 3 OCH 3 CH 3 H 3 C O O CH 2 Ph O O O O O O O O O Cl X no partial no partial no partial 4 each; can be either order -2 if steps unnumbered no partial -2 per error
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Name _______________________ Page 2 F.05.215FEP2 II. (40 points) A. Provide the complete, step-wise mechanism for the following observation ( JOC 2005 70 9354). Ph OH F F O O CF 3 Ph OH F O (CH 3 ) 3 N (H 3 C) 3 N O CF 3 F + Ph OH F F O O CF 3 Ph OH F O (CH 3 ) 3 N B. (a) Provide the complete IUPAC name (including stereochemical configuration) for the following: O OH OCH 3 H 3 C (b) Draw the structures for the following: the 2 most favorable enol forms of 2,4-dimethyl-1,3-cyclohexanedione 20 10 5 5 Ph OH F F O O CF 3 N(CH 3 ) 3 Ph OH F F O O CF 3 N(CH 3 ) 3 + ( S )-2-methoxy-2-methylhexanoic acid O OH CH 3 CH 3 OH O CH 3 CH 3 addition reaction mechanism = 4 tetrahedral intermediate = 4 elimination mechanism I = 4 alkoxide ion = 4 elimination mechanism II = 4 -3 per class of error: stereochem, punct, numbering, prefixes, name no partial no partial
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Name _______________________ Page 3 F.05.215FEP3 III.
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