Alkyl Halides (X = CI, Br or I): Assume AICI, is present if needed 2 of 2 C D G H. un acid catalyst [H+], or pyridine, is present if needed. OH OH CHJOH AA BB Cc DD EE FF GG HH Ketones, Aldehydes and Epoxides: Assume "then H,0" is included if a protonation step is needed J K L M A A & A V Acid Chlorides: Assume AICI, or pyridine is present if needed YY Other Reagents: 11 PCC in CH2C2 12 NazCr207, H2S04, H20 13 BH3 THF or 9-BBN, then H2O2, NaOH 14 Hg(OAc)2, H,0, then NABH, 15 O3, then Zn, HCI or DMS 16 MCPBA or CH,CO,H 17 Br2, light or NBS, heat 18 HBr 1 H3O* (dilute H2SO4) or H3O*, heat 2 conc. H2SO4, heat 3 NaOEt 21 Br2, FeBrz 22 Mg. Et20 23 Cl2, AICI, 24 SOCI2, pyridine 25 HNO3, H2SO, 26 fuming H2SO4 27 Fe, HCI; then NaOH 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 28 Zn(Hg), HCI 19 HBr, ROOR 29 KCN, or KCN + HCN 20 PBr3 30 CO2, then H3o* 31 (H'). HOʻ OH (-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 38 NaH, 25 °C „MgBr MeMgBr EIMgBr PhMgBr G1 G2 G3 G4 CuULi Me,Culi Et,Culi (PHCH2),CuLi 39 LIAI(OR),H, then H20 40 DIBAH, then H20 41 Br2. (H3O*) 42 Brz, NaOH 43 Pyridine G5 G6 G7 G8 MePh,P=CH2 PhyP=CHCH, PhyP=CHCO,Et PhyP=CHPH W1 w2 W3 W4
Alkyl Halides (X = CI, Br or I): Assume AICI, is present if needed 2 of 2 C D G H. un acid catalyst [H+], or pyridine, is present if needed. OH OH CHJOH AA BB Cc DD EE FF GG HH Ketones, Aldehydes and Epoxides: Assume "then H,0" is included if a protonation step is needed J K L M A A & A V Acid Chlorides: Assume AICI, or pyridine is present if needed YY Other Reagents: 11 PCC in CH2C2 12 NazCr207, H2S04, H20 13 BH3 THF or 9-BBN, then H2O2, NaOH 14 Hg(OAc)2, H,0, then NABH, 15 O3, then Zn, HCI or DMS 16 MCPBA or CH,CO,H 17 Br2, light or NBS, heat 18 HBr 1 H3O* (dilute H2SO4) or H3O*, heat 2 conc. H2SO4, heat 3 NaOEt 21 Br2, FeBrz 22 Mg. Et20 23 Cl2, AICI, 24 SOCI2, pyridine 25 HNO3, H2SO, 26 fuming H2SO4 27 Fe, HCI; then NaOH 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 28 Zn(Hg), HCI 19 HBr, ROOR 29 KCN, or KCN + HCN 20 PBr3 30 CO2, then H3o* 31 (H'). HOʻ OH (-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 38 NaH, 25 °C „MgBr MeMgBr EIMgBr PhMgBr G1 G2 G3 G4 CuULi Me,Culi Et,Culi (PHCH2),CuLi 39 LIAI(OR),H, then H20 40 DIBAH, then H20 41 Br2. (H3O*) 42 Brz, NaOH 43 Pyridine G5 G6 G7 G8 MePh,P=CH2 PhyP=CHCH, PhyP=CHCO,Et PhyP=CHPH W1 w2 W3 W4
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter16: Synthesis Workshop 1
Section: Chapter Questions
Problem 8CTQ
Related questions
Question
17
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
Step by step
Solved in 2 steps with 1 images
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Recommended textbooks for you
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning