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118B week 14 Exam 1 key

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Winter 2014 118B Midterm 1 Page 2 of 5 Last 4 digits of ID_______ 1. (32 pts) Predict the structure(s) of the expected major organic product(s). Unless mentioned otherwise, assume that all reagents are present in one mole equivalence. Show stereochemistry where needed and write NR if there is no reaction. Br (a) HBr,hυ H 2 O2 (b) (c) (d) (e) MCPBA CH2Cl 2 1) BH 3 , THF 2) H 2O 2, NaOH, H 2O Cl 1) CH3 Li, THF 2) O R 3) H3O+ NaOC 2H 5 C2 H5OH O or O Racemate -1 missing stereo OH 2 pts PC for any correct structural isomer HO R 2 pts PC for any structural isomer Racemate -1 missing stereo or OC 2 H 5 (f) 1) O3 , CH 2Cl2 2) S(CH3)2 H O O (g) CH 3 O NaSH, H 2O CH3 OH SH 2 pts PC for any structural isomer CH3 CHCl3 , KOC(CH 3)3