CHE 118B Midterm 1

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CHE 118B Midterm 1

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(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. (a) (b) 1. Hg(OAc) 2 , H 2O 2. NaBH 4 , NaOH, H 2 O 1) O3 (2 mol) 2) (CH3)2S (2 mol) + diastereomer OH 1 pt 3 pts O O O + H H H 2 pts 2 pts (c) (d) HBr, ROOR, hυ H 2O H 2SO 4 , HgSO 4 Br 3 pts enantiomers 1 pt O (e) TsO KOC(CH 3 )3 (CH 3) 3COH (f) Br NaOEt, EtOH any other isomer 2 pts PC (g) H 2 SO 4 ,Δ H 2O OH any other isomer 2 pts PC OH OH any other Br 2 , H 2O isomer

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