assignment2answers - CHM 3120 Assignment 2 1. a) Show how...

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1 CHM 3120 Assignment 2 1. a) Show how you would make the syn isomer of the following and explain the selective formation of that isomer. OH OH OHC MgBr H 3 CH O H 3 H O MgBr MgBr H 3 H HO H 3 OH H OHC CH 3 OH CH 3 OH + favored disfavored Major H Determine using Felkin-Ahn model How would you make the anti isomer? Explain your reasoning. NaBH 4 H 3 O H 3 O NaBH 4 CH 3 O H 3 H HO H 3 H OH CH 3 OH CH 3 OH CH 3 OH favored disfavored Major Why anti? CH 3 O 2. A student trying to find the best method to synthesize a drug sample makes the following observation. Explain her results.
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2 OO H O H + Reagent LiAlH 4 LiBH(iBu) 3 3 99 : : 1 1 H 3 CH CH 3 O H 3 O H 3 C H 3 H OH H 3 C H 3 H CH 3 HO CH 3 CH 3 favored disfavored OH OH Major O Nu Nu When the nucleophile is small (LiAlH 4 ), the top pathway is favored but the bottom is also possible. The ratio is only 3:1 When the nucleophile is large (LiBH(iBu) 3 ), the top pathway is favored but the bottom is very difficult. The ratio is much higher (99:1) 3. Propose a synthetic scheme to prepare the indicated isomer using the following sequence. Explain the
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assignment2answers - CHM 3120 Assignment 2 1. a) Show how...

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