From the lists of available reagents select the one(s) you would use to in a preparation of acetophenone (phenyl methyl ketone) from methyl benzoate. (In no case are more than three steps necessary.) Reagents Available a. CH3COCI, AICI3 d. CH3CHO b. (CH3)2CuLi e. Hg(OAc)2, H2O; then NaBH4 g. Mg h. NaOH, H₂O j. SOCI₂ c. CH3MgBr, then H3O+ H30* f. KMnO4, H₂O i. Dess-Martin periodinane List reagents by letter in the order that they are used; example: fa. Reagents used:

CH3 NH Coniine Coniine, CH N. i the toxic principle of the poison hemlock drunk by Socrates. It can be synthesized from acrylonitrile (H,C=CHCN) and ethyl 3-oxohexanozte. The synthesis proceeds as follows 1. Deprotonation of ethyl 3-oxohexanoate to form enolate anion 1; 2. Michzel addition to acrylonitrile to form intermediate 2; 3. Protonation to form Michzel adduct 3; 4. Ester hydrolysis and decarboxylation to form oxonitrile 4; 5. Reduction to form oxoamine 5; 6. Cyclization to form imine 6: 7. Catalytic hydrogenation to form Conine. Draw the structures of enolate anion 1 and imine 6. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading • Draw enolate anions in their carbanion form • Drzw one structure per sketcher. Add zdditional sketchers using the drop-down menu in the bottom right corner. • Show the correct order of synthesis by drawing a reaction arrow…

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This synthesis scheme was designed using the reaction roadmaps. (Reaction roadmaps allow you to "navigate" between the different functional groups and their behavior in chemical reactions.) compound c compound b ● W compound a compound f MAVI compound e m compound d Reagents HBr HBr, H₂O₂, hv a. b. c. H₂O, H₂SO4 d. Br₂ e. Cl₂ f. H₂, Pd Br₂, H₂O Cl₂, H₂O OsO4 then NaHSO3 #[ ] در g. h. i. j. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If there are alternative structures, draw the most stable one. • If the reaction produces a racemic mixture, draw both stereoisomers. Separate structures with + signs from the drop-down menu. k. I. m. n. O. p. Hg(OAc)2, H₂O then NaBH4 BH3 then H₂O₂, NaOH O3 then (CH3)2S In this synthesis, reagents from the table are used to carry out the indicated steps (shown in blue). In the box below, draw the structure of compound d. q. r. 2 equivalents of NaNH₂ H2, Lindlar's catalyst Na/NH3 H₂SO4, HgSO4 (sia)2BH then H₂O₂, NaOH 1…