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Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter22: Synthesis Workshop 2
Section: Chapter Questions
Problem 5CTQ
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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
Propose an efficient synthesis for the transformation below (enter the code for each reagent in the appropriate space; the word None in that space). HO. :Step 3 :Step 4 Step 1 :Step 2
Transcribed Image Text:Propose an efficient synthesis for the transformation below (enter the code for each reagent in the appropriate space; the word None in that space). HO. :Step 3 :Step 4 Step 1 :Step 2
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