Question: 1) (20 points) Predict the missing reagents to accomplish the following transformations. a) H3C H3 C CH3 CH3 b) H3C CH3 H3 C CH3 OH

1) (20 points) Predict the missing reagents to accomplish the following transformations. a) H3C H3 C CH3 CH3 b) H3C CH3 H3 C CH3 OH CH3 CH3 C)H3 C CH3 H3 C CH3 OH OH 2) (20 points) Predict the expected products when the following substrates are treated with the reagents listed below. o 1) HaC' CH3 H2C NaNH2 2) HaO+ CH3 CH3 1) BH3 THF H2C 2) H202, NaOH D HgSO4, H2SO4 H20Choose the correct sequence of reactions to afford the following 3-step transformation (you need to identify what reagents and in what order x, y, z they are added to accomplish the trans alkene). Draw the expected intermediates 1 and 2 for full credit CH3 X y Z intermediate 1 intermediate 2 a) x = Na, NH3 y = CH3Br z = NaNH2 b) X = CH3Br y = Na, NH3 Z = NaNH2 c) x = NaNH2 y = Na, NH3 Z = CH3Br d) x = NaNH2 y = CH3Br z = Na, NH3 Extra credit question (5 points) Show how you would synthesize the following compound starting with acetylene and any other compounds and reagents as needed. OH What reagents? H = H ,CH3 In what order? H3 C OH
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