3 NaOEt 4 t BuOK 5 H Pt 6 H Lindlar s catalyst 7 Na NH3 8 LAH or xs LAH then H O 9 NaBH CH OH 10 NaBH CN pH 5 Grignard Wittig

Question

3 NaOEt 4 t BuOK 5 H Pt 6 H Lindlar s catalyst 7 Na NH3 8 LAH or xs LAH then H O 9 NaBH CH OH 10 NaBH CN pH 5 Grignard Wittig and Gilman Reagents Assume then H O is included if a protonation step is needed MeMgBr EtMgBr PhMgBr PhCH MgBr G1 G2 G3 G4 Ph Me Culi Et Culi Ph Culi PhCH Culi G6 CH OH PhyP CH W1 G7 TT CI then H O NaOH 14 Hg OAc H O then NaBH 15 03 then Zn HCI or DMS 16 MCPBA or CH CO3H 17 Br light or NBS heat 18 HBr 19 HBr ROOR 20 PBr3 G8 COH K Ph P CHCH PhP CHCO Et Ph P CHPh W2 W3 W4 OH G9 13 UU CHX D E F A B C Alcohols Assume an acid catalyst H or pyridine is present if needed OH G5 G10 PH Reactant reagent List For Final Exam Enter code or letter in the appropriate boxes Note Exam responses are case insensitive Alkyl Halides X Cl Br or I Assume AICI is present if needed MgBr UV S T U V W Acid Chlorides Assume AICI or pyridine is present if needed OH N 24 SOCI pyridine 25 HNO3 H SO4 26 fuming H SO4 27 Fe HCl then NaOH 28 Zn Hg HCI 29 KCN or KCN PHCN 30 CO then H O 31 TH H HH AA BB CC GG DD EE FF Ketones Aldehydes and Epoxides Assume then H O is included if a protonation step is needed ww 32 NH 1 or 2 equiv 33 CH3NH 1 or 2 equiv 34 CH NH 1 or 2 equiv 35 EtNH 1 or 2 equiv 36 PhCH NH 1 or 2 equiv 37 LDA 78 C 38 NaH 25 C OH 39 LIAI OR H then H O 40 DIBAH then H O 41 Br H O 42 Br NaOH OH H O G OH XX A X Z 4 L H 47 CUCN 48 HBF4 49 H O heat 50 H PO 51 52 LOH Lo Len H2 HH2 ZZ OH R NH

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