BÀI GIẢNG ORGANIC CHEMISTRY chapter10

ORGANIC CHEMISTRY Dr Nam T S Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 38647256 ext 5681 Email: ptsnam@hcmut.edu.vn Chapter 10: ALCOHOLS-PHENOLS NOMENCLATURE OF ALCOHOLS Common names: alkyl + alcohol IUPAC names: hydrocarbon + ol PREPARATION OF ALCOHOLS Alcohols from alkenes Markovnikov’s rule H2SO4, H3PO4… Anti-Markovnikov Alcohols from alkyl halides Carbocation rearrangements may occur Alcohols from aldehydes & ketones Aldehydes & ketones can also be reduced using LiAlH4, H2/Pt, Pd, Ni, Ru … Alcohols from carboxylic acids & derivatives Can NOT use NaBH4, H2/Pt, Pd, Ni, Ru… for acids 10 NOMENCLATURE OF PHENOLS 26 PREPARATION OF PHENOLS 27 REACTIONS OF PHENOLS Halogenation reactions Strong activating group Non-polar solvent Polar solvent NO monobromination 28 Nitration reactions NOT necessary to use mixture of concentrated HNO3 & H2SO4 Sulfonation reactions 29 FriedelCrafts Alkylation reactions FriedelCrafts Acylation reactions 30 O-acylations of phenols NO Lewis acid 31 The Kolbe-Schmitt reaction 32 33 Preparation of aryl ethers Can NOT prepare aryl ether directly from the reaction of phenol & alcohol in the presence of acid catalyst 34 Cleavage of aryl ethers by hydrogen halides 35 Reaction mechanism: SN2 NOTE: 36 Oxidation of phenols 37 Polymerization with formaldehyde Electrophilic aromatic substitution reactions 38 39 40