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Identify the reagent needed to accomplish the transformation below (enter the appropriate code from the reagent list) OH IReagentl

Identify the reagent needed to accomplish the transformation below (enter the appropriate code from the reagent list) OH IReagentl

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter24: Amines And Heterocycles
Section24.SE: Something Extra
Problem 59AP
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Identify the reagent needed to accomplish the transformation below (enter the appropriate code from the reagent list) OH IReagent
Transcribed Image Text:Identify the reagent needed to accomplish the transformation below (enter the appropriate code from the reagent list) OH IReagent
Alkyl Halides (X = CI, Br or I): Assume AICI, is present if needed 2 of 2 G un acid catalyst [H+], or pyridine, is present if needed. он OH OH CHJOH AA BB DD EE FF GG HH Ketones, Aldehydes and Epoxides: Assume "then H,0" is included if a protonation step is needed K. P R V Acid Chlorides: Assume AICI, or pyridine is present if needed YY zZ Other Reagents: 11 PCC in CH2C2 21 Br2, FeBr3 22 Mg. Et,0 23 Cl2, AICI3 24 SOCI2, pyridine 25 HNO3, H2SO4 26 fuming H2SO4 1 H3O* (dilute H2SO4) or H3O*, heat 2 conc. H2SO4, heat 3 NaOEt 12 NazCr207, H2S04, H2O 13 BH3•THF or 9-BBN, then H2O2, NaOH 14 Hg(OAc)2, H2O, then NaBH4 15 O3, then Zn, HCI or DMS 16 MCPBA or CH;CO3H 17 Br2, light or NBS, heat 4 t-BUOK 5 H2, Pt 6 H2, Lindlar's catalyst 7 Na, NH3 8 LAH or xs LAH, then H20 9 NABH4, CH3OH 10 NABH,CN, pH 5 27 Fe, HCI; then NaOH 28 Zn(Hg). НCI 29 KCN, or KCN + HCN 30 CO2, then H30* 18 HBr 19 HBr, ROOR 20 PB13 31 (H*]. HOʻ 32 NH3 (1 or 2 equiv.) 33 CH,NH2 (1 or 2 equiv) 34 (CH3)½NH (1 or 2 equiv) 35 EINH2 (1 or 2 equiv) 36 PHCH,NH2 (1 or 2 equiv). 37 LDA, -78 °C (-H20) Grignard, Wittig and Gilman Reagents: Assume "then H,0" is included if a protonation step is needed MgBr MeMgBr EtMgBr 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 Br2. [H3O*] 42 Br2, NaOH 43 Pyridine G5 G6 G7 G8 MePh,P=CH2 PhyP=CHCH3 PhyP=CHCO,Et PhyP=CHPH W1 w2 W3 W4
Transcribed Image Text:Alkyl Halides (X = CI, Br or I): Assume AICI, is present if needed 2 of 2 G un acid catalyst [H+], or pyridine, is present if needed. он OH OH CHJOH AA BB DD EE FF GG HH Ketones, Aldehydes and Epoxides: Assume "then H,0" is included if a protonation step is needed K. P R V Acid Chlorides: Assume AICI, or pyridine is present if needed YY zZ Other Reagents: 11 PCC in CH2C2 21 Br2, FeBr3 22 Mg. Et,0 23 Cl2, AICI3 24 SOCI2, pyridine 25 HNO3, H2SO4 26 fuming H2SO4 1 H3O* (dilute H2SO4) or H3O*, heat 2 conc. H2SO4, heat 3 NaOEt 12 NazCr207, H2S04, H2O 13 BH3•THF or 9-BBN, then H2O2, NaOH 14 Hg(OAc)2, H2O, then NaBH4 15 O3, then Zn, HCI or DMS 16 MCPBA or CH;CO3H 17 Br2, light or NBS, heat 4 t-BUOK 5 H2, Pt 6 H2, Lindlar's catalyst 7 Na, NH3 8 LAH or xs LAH, then H20 9 NABH4, CH3OH 10 NABH,CN, pH 5 27 Fe, HCI; then NaOH 28 Zn(Hg). НCI 29 KCN, or KCN + HCN 30 CO2, then H30* 18 HBr 19 HBr, ROOR 20 PB13 31 (H*]. HOʻ 32 NH3 (1 or 2 equiv.) 33 CH,NH2 (1 or 2 equiv) 34 (CH3)½NH (1 or 2 equiv) 35 EINH2 (1 or 2 equiv) 36 PHCH,NH2 (1 or 2 equiv). 37 LDA, -78 °C (-H20) Grignard, Wittig and Gilman Reagents: Assume "then H,0" is included if a protonation step is needed MgBr MeMgBr EtMgBr 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 Br2. [H3O*] 42 Br2, NaOH 43 Pyridine G5 G6 G7 G8 MePh,P=CH2 PhyP=CHCH3 PhyP=CHCO,Et PhyP=CHPH W1 w2 W3 W4
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