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 to1) (20 points) Predict the missing reagents to 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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