QUESTION 2 From the list provided, choose the reaction conditions that will bring about the overall transformation shown below OH OA CH3CH2OH, H2504 (cat) OB (1) Mg, ether; (2) 2-methyloxirane: (3) H30t Oc MCPBA OD (1) LIAIH4, ether: (2) H3o* OE (1) CH3NH2, pH 5: (2) NABH3CN O (1) PPhg: (2) Bult (3) benzaldehyde oa (1) PPhy (2) Duli: (3) acetophenone OK (1) Mg, ether; (2) acetone; (3) HJo* OL NaCIO2, NaH2PO4. 2-methyl-2-butene ol (1) (COC)2, DMSO; (2) NEtg OK (CH)2NH, pH 5 OL H2NNH2, KOH, heat OM None of the other reaction conditions listed will produce this overal transformation ON Crog, H2S04 H20 oo H2NNH2, pH-5

synthesis for the following reaction.

35) What is the correct order of reagents to achieve the following synthesis? A) i) NH2NH2, H3O* (aq); ii) NaOH (aq) & A Reactant structure: Target molecule: B) i) LIAIH«, THF; ii) H2O & A C) i) NABH4, EtOH; ii) H2O & A CH3 CH3 D) i) DIBAL-H ii) H3O* (aq) & A

9. Write structural formulas for the major organic product(s) for the following reactions. Be sure to indicate stereochemistry when relevant. (CH;CH,CH,),CuLi (a) Cl Br PAL2 (b) HO (c) CH;CH,CH,CH,OH C,H5MgBr 10. Propose a reasonable mechanism for the following reaction Be sure to include all intermediates. (transition states are not necessary) Br Br hv CH3-CH=C(CH3)2 + Br, ČH,-CH=C(CH3)2 CH2=CH–Ċ(CH3)2 11. Indicate how each of the following compounds could be prepared using the given starting material CH;CH,CH,CH3 CH;CH,CH,CH,Br CH;CH,CH,CH3 H,C=CH-CH=CH2 Br CH;CHCH,CH3 CH;CH=CCH,CH3 CH3