
4) Predict the product (A) of the following reaction. 1. KMnO4/NaOH/H20 2. H30* SOCI2 pyridine (CH3)2CHCH2OH pyridine A
draw final products, mechanisms
and intermediates
c) 1. CH3CH2CI, AICI: 2. KMnO4 3. SOCl2, pyridine 4. H2N-CH2CH3 , pyridine 5. LiAlH4 6. H307 workup
NaBH4 CC Hg(OAC)2 H20, THE NaOH 1. Hg(O2CCF3)2, 'ProH 2. NaBH4, NaOH 1. BHz •THF 2. H2O2, HOⓇ R-OH + Nax — NaCN DMSO TSCI pyridine ОН MSCI pyridine NasMe DMSO cat. HA MeOH + g. Arrange in the Increasing acidity order HẠO ROH RC=CH HA NHA RH. cold KMnO4, HOor 1. Os04 2. NaHSO3 MICH3 1. mCPBA 2. H+, CH3OH, H2O 1. mCPBA 2. NaOCH3, H20 H2O / H+ Hg(OAC)2 H2O, THE NaBH4 NaOH 1. BH3 THF 2. HaO2...
Carboxylic acid problems 1) KMnO4, NaOH 1) KMnO4. NaOH Heat 2) H30 Cr Heat 2) H2O*cr 1) Ag20 or Ag(NH3)2*OH 1) Og 2) H,02 H2) H30°C KMnO4 CH3(CH2)6CH2 CH2(CH2)CH2COH C=C HH H30+ Oleic acid HO 1) KMnO4, NaOH Heat 2) H30*cr CH3 CH3CHCH2CH2CH2OH 4-Methyl-1-pentanol H30+ OH 1) H.CO. CH3CH2CH2CH2CH2CH Hexanal CHE 212 CH 15 & 16 Cathexaulic Acids. 22
th) HO NIH2 (Acetaminophen) Pyridine . CH3 MgBr Excess 0) 2. H20 COOH 0) 1. LiAIH4 2 H20
OH H20 H2SO4 ОН H2, Pd (1) MCPBA (2) H30+ KMnO4 NaOH, cold
bbb.) Cl2 FeBrz HO CCC.) H 1. KMnO4/NaOH(aq)/A 2. H307 ddd.) CN oleum eee.) NO2 1. Sn, HCI, A 2. HNO2, HCI 3. HBF4 H fff) Hz. Pd 4500 psi 999) OH 1. XS KMnO, NaOH(aq) 2. H,09 hhh.) 1. PrLI, THF 2. NHCl(aq) 1.) CH,BF4 Br SO,/H,SO 1.04. CHÚCOH 2. HO 11.) -Br 1. Mg/THF 2. HO
OH 1. NaOCHZ 2. H20 CO2H acid catalyst hint: - BuOH 1 2 NaOH, H2O heat 1. (CH3)2CuLi, ether 2. H30* H 3 1. NaOCH3 u 1. H307 2. heat 2. Br Br 5 6
CH3 Heat KMnO4 NaOH SOCI2 3) 16) H2O (CH3)2NH CH:C00 8) CH3OH AICI (CH3)2Culi NaOH 11) LAH (CH:CO), 14) 13) CH3COCI
6x. Fill in the missing items. 1.) CH3 Na BHз 2. HCI 1.)OH, H20 2.) H30®, heat * B. . .. 1.) NaOH, H20 2. NaOH, heat NaCN CH3OH R но он Н,00 1.)LIAIH 4 , THE S 2. H,00