Ketones, Aldehydes and Epoxides: Assume "then H,0" is included if a protonation step is needed R K V Acid Chlorides: Assume AICI, or pyridine is present if needed w Y YY Other Reagents: 1 H3O* (dilute H,SO,) or H3O*, heat 2 conc. H,SO4, heat 11 PCC in CH,Cl2 12 Na,Cr2O7, H2SO,, H2O 13 BH3 THF or 9-BBN, then H2O2, NAOH 14 Hg(OAc)2, H2O, then NaBH, 15 O3, then Zn, HCI or DMS 16 MCPBA or CH3CO3H 17 Brz, light or NBS, heat 18 HBr 19 HBr, ROOR 21 Brz, FeBr3 22 Mg. Et,0 23 Cl2, AICI3 24 SOCI2, pyridine 25 HNO3, H2SO4 26 fuming H2SO4 27 Fe, HCI; then NaOH 3 NaOEt 4 t-BUOK 5 H2, Pt 6 H2, Lindlar's catalyst 7 Na, NH3 8 LAH or xs LAH, then H20 9 NABH4, CH,OH 10 NABH;CN, pH 5 28 Zn(Hg), HCI 29 KCN, or KCN + HCN 20 PBr3 30 CO2, then H3O* 31 (H'). HO (-H2O) Grignard, Wittig and Gilman Reagents: Assume "then H,0" is included if a protonation step is needed 32 NH3 (1 or 2 equiv.) 33 CH;NH2 (1 or 2 equiv) 34 (CH3)2NH (1 or 2 equiv) 35 EINH2 (1 or 2 equiv) 36 PHCH,NH2 (1 or 2 equiv). 37 LDA, -78 °C MgBr MeMgBr EIMgBr PhMgBr G1 G2 G3 G4 CuLi Me,CuLi Et,Culi (PHCH2),CuLi 38 NaH, 25 °C 39 LIAI(OR),H, then H20 40 DIBAH, then H2O 41 Brz. [H3O*] 42 Brz, NaOH 43 Pyridine G5 G6 G7 G8 MePh,P=CH2 PhyP=CHCH, PhyP=CHCO,Et PhyP=CHP. W1 w2 W3 W4

Ketones, Aldehydes and Epoxides: Assume "then H,0" is included if a protonation step is needed R K V Acid Chlorides: Assume AICI, or pyridine is present if needed w Y YY Other Reagents: 1 H3O* (dilute H,SO,) or H3O, heat 2 conc. H,SO4, heat 11 PCC in CH,Cl2 12 Na,Cr2O7, H2SO,, H2O 13 BH3 THF or 9-BBN, then H2O2, NAOH 14 Hg(OAc)2, H2O, then NaBH, 15 O3, then Zn, HCI or DMS 16 MCPBA or CH3CO3H 17 Brz, light or NBS, heat 18 HBr 19 HBr, ROOR 21 Brz, FeBr3 22 Mg. Et,0 23 Cl2, AICI3 24 SOCI2, pyridine 25 HNO3, H2SO4 26 fuming H2SO4 27 Fe, HCI; then NaOH 3 NaOEt 4 t-BUOK 5 H2, Pt 6 H2, Lindlar's catalyst 7 Na, NH3 8 LAH or xs LAH, then H20 9 NABH4, CH,OH 10 NABH;CN, pH 5 28 Zn(Hg), HCI 29 KCN, or KCN + HCN 20 PBr3 30 CO2, then H3O 31 (H'). HO (-H2O) Grignard, Wittig and Gilman Reagents: Assume "then H,0" is included if a protonation step is needed 32 NH3 (1 or 2 equiv.) 33 CH;NH2 (1 or 2 equiv) 34 (CH3)2NH (1 or 2 equiv) 35 EINH2 (1 or 2 equiv) 36 PHCH,NH2 (1 or 2 equiv). 37 LDA, -78 °C MgBr MeMgBr EIMgBr PhMgBr G1 G2 G3 G4 CuLi Me,CuLi Et,Culi (PHCH2),CuLi 38 NaH, 25 °C 39 LIAI(OR),H, then H20 40 DIBAH, then H2O 41 Brz. [H3O*] 42 Brz, NaOH 43 Pyridine G5 G6 G7 G8 MePh,P=CH2 PhyP=CHCH, PhyP=CHCO,Et PhyP=CHP. W1 w2 W3 W4

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter26: Aldol And Claisen Reactions

Section: Chapter Questions

Problem 9CTQ

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