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Propose an efficient synthesis for the transformation below. Enter the appropriate code from the Reagent list. NO2 Br Step 1 Step 2 : Step 3 : Step 4

Propose an efficient synthesis for the transformation below. Enter the appropriate code from the Reagent list. NO2 Br Step 1 Step 2 : Step 3 : Step 4

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.68P
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Reactant/reagent List Enter code (# or letter) in the appropriate boxes. Alkyl Halides (X = CI, Br or I): Assume AICI, is present if needed CH,X X, B A D E F G H H2 Alcohols: Assume an acid catalyst [H+], or pyridine, is present if needed. он HO. OH CH,OH HO HO, он AA BB DD EE FF GG HH HH2 Ketones, Aldehydes and Epoxides: Assume "then H,0" is included if a protonation step is needed Ph J K M Ph. Ph Ph Ph Ph T U V w Acid Chlorides: Assume AICI, or pyridine is present if needed Ph TT U UV ww XX YY Reactant/reagent List Enter code (# or letter) in the appropriate boxes. Other Reagents: 21 Br2, FeBr3 22 Mg. Et,0 23 Cl2, AICI3 24 SOCI2, pyridine 43 NANO2, HCI 1 H30* (dilute H2SO4) or H30*, heat 2 conc. H,SO4, heat 11 PCC in CH,Cl2 12 Na,Cr2O7, H2SO4, H2O 13 BH THF or 9-BBN, then H2O2, NaOH 14 Hg(OAc)2, H2O, then NaBH, 25 HNO3, H2SO4 15 O3, then Zn, HCI or DMS 16 MCPBA or CH;CO3H 17 Br2, light or NBS, heat 44 CuBr 45 CuCl 3 NaOEt 46 Cul 4 t-BUOK 47 CUCN 26 fuming H,SO4 27 Fe, HCI; then NaOH 48 HBF. 49 H2O, heat 50 H3PO2 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 28 Zn(Hg), HCI 29 KCN, or KCN + HCN 18 HBr 19 HBr, ROOR 30 CO2, then H30* 20 PBr3 31 (H*]. HO он (-H2O) Grignard, Wittig and Gilman Reagents: Assume "then H,0" is included if a protonation step is needed 32 NH, (1 or 2 equiv.) 33 CH;NH2 (1 or 2 equiv) 34 (CH3)½NH (1 or 2 equiv) 35 EINH, (1 or 2 equiv) 36 PHCH,NH2 (1 or 2 equiv). 37 LDA, -78 °C 38 NaH, 25 °C 51 „MgBr MeMgBr EtMgBr PhMgBr PHCH;MgBr G1 G2 G3 G4 G5 NH2 52 CuLi Me;Culi Et,Culi Ph,Culi (PHCH2)hCuli 2 39 LIAI(OR);H, then H20 40 DIBAH, then H20 41 Brz. [H3O*] 42 Br2, NaOH G6 G7 G8 G9 G10 Ph;P=CH2 Ph3P=CHCH3 PhyP=CHCO¿Et PhyP=CHPH W1 w2 W3 W4
Transcribed Image Text:Reactant/reagent List Enter code (# or letter) in the appropriate boxes. Alkyl Halides (X = CI, Br or I): Assume AICI, is present if needed CH,X X, B A D E F G H H2 Alcohols: Assume an acid catalyst [H+], or pyridine, is present if needed. он HO. OH CH,OH HO HO, он AA BB DD EE FF GG HH HH2 Ketones, Aldehydes and Epoxides: Assume "then H,0" is included if a protonation step is needed Ph J K M Ph. Ph Ph Ph Ph T U V w Acid Chlorides: Assume AICI, or pyridine is present if needed Ph TT U UV ww XX YY Reactant/reagent List Enter code (# or letter) in the appropriate boxes. Other Reagents: 21 Br2, FeBr3 22 Mg. Et,0 23 Cl2, AICI3 24 SOCI2, pyridine 43 NANO2, HCI 1 H30* (dilute H2SO4) or H30*, heat 2 conc. H,SO4, heat 11 PCC in CH,Cl2 12 Na,Cr2O7, H2SO4, H2O 13 BH THF or 9-BBN, then H2O2, NaOH 14 Hg(OAc)2, H2O, then NaBH, 25 HNO3, H2SO4 15 O3, then Zn, HCI or DMS 16 MCPBA or CH;CO3H 17 Br2, light or NBS, heat 44 CuBr 45 CuCl 3 NaOEt 46 Cul 4 t-BUOK 47 CUCN 26 fuming H,SO4 27 Fe, HCI; then NaOH 48 HBF. 49 H2O, heat 50 H3PO2 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 28 Zn(Hg), HCI 29 KCN, or KCN + HCN 18 HBr 19 HBr, ROOR 30 CO2, then H30* 20 PBr3 31 (H*]. HO он (-H2O) Grignard, Wittig and Gilman Reagents: Assume "then H,0" is included if a protonation step is needed 32 NH, (1 or 2 equiv.) 33 CH;NH2 (1 or 2 equiv) 34 (CH3)½NH (1 or 2 equiv) 35 EINH, (1 or 2 equiv) 36 PHCH,NH2 (1 or 2 equiv). 37 LDA, -78 °C 38 NaH, 25 °C 51 „MgBr MeMgBr EtMgBr PhMgBr PHCH;MgBr G1 G2 G3 G4 G5 NH2 52 CuLi Me;Culi Et,Culi Ph,Culi (PHCH2)hCuli 2 39 LIAI(OR);H, then H20 40 DIBAH, then H20 41 Brz. [H3O*] 42 Br2, NaOH G6 G7 G8 G9 G10 Ph;P=CH2 Ph3P=CHCH3 PhyP=CHCO¿Et PhyP=CHPH W1 w2 W3 W4
Propose an efficient synthesis for the transformation below. Enter the appropriate code from the Reagent list. NO2 Br Step 2 Step 3 Step 4 Step 1
Transcribed Image Text:Propose an efficient synthesis for the transformation below. Enter the appropriate code from the Reagent list. NO2 Br Step 2 Step 3 Step 4 Step 1
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