Practice 1-2 A - Chemistry 436 Professor Paul J....

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1 Chemistry 436 Professor Paul J. Hergenrother University of Illinois, Urbana-Champaign Answers to Test Old Test #1b - You must use pencil for the exam. - Illegible answers cannot be graded and will receive no credit. NAME:________________________________ 1 21 points 2 18 points 3 9 points 4 42 points 5 10 points total 100 points
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2 1. Predict the major product in the following transformations. Please show stereochemistry, where appropriate. If there is no reaction, simply write “No Reaction”: (3 points each) H O O Ph 3 P (1 equivalent) a) O LDA -78 O C Br (this enantiomer only) b) OH HO OH PCC (3 equivalents) c) O LiAlH 4 then aqueous workup d) O f) (CH 3 ) 2 CuLi g) O NaH (1 equiv.) room temp. MeI O O OH e) H O OSiR 3 Ph 3 P F CrO 3 H 2 SO 4 H 2 O H O O O is OK 1 pt for racemic O O OH H Cannot oxidize tertiary alcohol- review mechanism for oxidation (you need a proton on carbon a) a OH O O strongly acidic conditions enable double bond to migrate into conjugation initial product final product 1pt O O O O aq.
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Practice 1-2 A - Chemistry 436 Professor Paul J....

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