Reagents - 1. LiAlH 4 /Et 2 O or THF; 2. NH 4 Cl Mg/Et 2 O...

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Reagents ( List not meant to be comprehensive! Bold-faced reagents are new this semester ) Br 2 or Cl 2 /CH 2 Cl 2 Br 2 or Cl 2 / h ν and/or heat conc. KOH/EtOH or KOBu t /Bu t OH, or KOBu t /DMSO Li or Na or K conc. HBr or conc. HCl HBr (dry)/peroxides/heat PBr 3 /heat or PCl 3 /heat (PCl 3 is alternative to SOCl 2 ) dil. aq. H 2 SO 4 Cl 2 /H 2 O or Br 2 /H 2 O HS - or RS - or N 3 - or N C- or HO - or RO - in polar protic or polar aprotic solvent NaNH 2 / NH 3 (liq.) ; MCPBA (RCO 3 H)/Na 2 CO 3 SOCl 2 /heat H 2 (1 atm.)/EtOH/Pt or Pd or Ni 1. O 3 /-78 °C; 2. (CH 3 ) 2 S or Zn/HOAc conc. H 2 SO 4 or H 3 PO 4 or KHSO 4 (catalytic amount) 1. BH 3 /THF; 2. H 2 O 2 /HO - H 2 (1 atm.)/EtOH/Lindlar's cat. 1. Na or Li or K/NH 3 (liq.) ; 2. NH 4 Cl 1. KMnO 4 , HO - /heat; 2. NH 4 Cl TsOH CH 3 SO 2 Cl (MsCl) or CH 3 C 6 H 5 SO 2 Cl (TsCl)/pyridine NBS/peroxides/heat RCl/AlCl 3 or ROH/H 2 SO 4 or Alkene/H 2 SO 4 conc. HNO 3 / conc. H 2 SO 4 HgSO 4 /H 2 O/THF/heat RC(=O)Cl or RC(=O) 2 O/AlCl 3 Br 2 or Cl 2 /FeX 3 (X = Br or Cl) SO 3 /H 2 SO 4 CO, HCl, AlCl 3 , heat, pressure H 2 NNH 2 /KOH/200 °C or Zn(Hg) x / conc. HCl H 2 CrO 4 (CrO 3 /H 2 SO 4 )/heat RS - (R = H, alkyl, or aryl) 1. NaBH 4 /CH 3 OH; 2. NH 4 Cl
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Unformatted text preview: 1. LiAlH 4 /Et 2 O or THF; 2. NH 4 Cl Mg/Et 2 O or THF or Li (2 eq.)/THF or hexane Pyridinium chlorochromate (PCC) CH 2 Cl 2 ROH, H 2 SO 4 (cat.) HOCH 2 CH 2 OH/TsOH (cat.) NaCN or KCN/H 3 O + 2RLi/CuX R 2 Cu-Li + OsO 4 (cat.)/(CH 3 ) 3 COOH/HO-/ (CH 3 ) 3 COH OsO 4 (cat.)/(CH 3 ) 3 COOH/HO-/ HIO 4 (CH 3 ) 3 COH RNH 2 , p H ~ 5 Ph 3 P=CR 2 (know how to produce this phosphorane from Ph 3 P and R 2 CHBr) 1. NaBH 3 CN/pH 6; 2. Neutralize NaNO 2 /HCl (HNO 2 )/0 C HBF 4 KI BF 3 Sn or Fe/ conc. HCl AgNO 3 (NH 3 ) 2 CH 3 I/Ag 2 O H 3 PO 2 I 2 /HO-1. Hg(OAc) 2 /H 2 O/THF; 2. NaBH 4 /CH 3 OH 1. DIBAH/ toluene/-78 C; 2. NH 4 Cl NaI/acetone 1. HO-/300 C; 2. H 3 O + SnCl 2 / conc. HCl ( n-Bu) 4 N + F-(TBAF) I 2 /Cu 1+ KMnO 4 (cold, dil.)/H 2 O 1. R 2 BH /THF; 2. CH 3 CO 2 H (HOAc) (CH 3 ) 3 SiCl/Et 3 N 1. Hg(OAc) 2 /ROH/THF; 2. NaBH 4 /C 2 H 5 OH...
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This note was uploaded on 09/26/2008 for the course CH 318N taught by Professor Willson during the Spring '08 term at University of Texas at Austin.

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