tailieunhanh - Chapter 10: ALCOHOLS-PHENOLS

Common names: alkyl + alcohol. IUPAC names: hydrocarbon + ol. Carbocation rearrangements may occur. Aldehydes and ketones can also be reduced using LiAlH Pd, Ni, Ru. | ORGANIC CHEMISTRY Dr Nam T. S. Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 8647256 ext. 5681 Email: ptsnam@ Chapter 10: ALCOHOLS-PHENOLS NOMENCLATURE OF ALCOHOLS Common names: alkyl + alcohol IUPAC names: hydrocarbon + ol PREPARATION OF ALCOHOLS Alcohols from alkenes H2SO4, H3PO4 Markovnikov’s rule 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 Alcohols from Grignard reagents REACTIONS OF ALCOHOLS Reactions of proton in -OH Can NOT react with NaOH Dehydration reactions isomerization Primary alcohol Internal alkene 1-alkenes can NOT be prepared using the dehydration reaction Only in acidic conditions Conversion of alcohols to alkyl halides isomerization PCl3, SOCl2 can also be used Can NOT work for tertiary alcohols due to steric hindrance NO carbocation formation, NO rearrangement Conversion of alcohols to ethers Only effective for primary alcohols Only for symmetric ether Reaction mechanism: Fisher esterification reactions Need acid catalyst Reversible reaction Reaction mechanism: Oxidation reactions Can NOT be isolated PCC: pyridinium chlorochromate PHENOLS SP2 Carbon SP3 Carbon Some naturally occurring phenols NOMENCLATURE OF PHENOLS PREPARATION OF PHENOLS REACTIONS OF PHENOLS Halogenation reactions Strong activating group Polar solvent Non-polar solvent NO monobromination NOT necessary to use mixture of concentrated HNO3 & H2SO4 Nitration reactions Sulfonation reactions Friedel-Crafts Alkylation reactions Friedel-Crafts Acylation reactions O-acylations of phenols NO Lewis acid The Kolbe-Schmitt reaction Preparation of aryl ethers Can NOT prepare aryl ether directly from the reaction of phenol & alcohol in the presence of acid catalyst Cleavage of aryl ethers by hydrogen halides Reaction mechanism: NOTE: SN2 Oxidation of phenols Polymerization with formaldehyde Electrophilic aromatic substitution reactions | ORGANIC CHEMISTRY Dr Nam T. S. Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 8647256 ext. 5681 Email: ptsnam@ Chapter 10: ALCOHOLS-PHENOLS NOMENCLATURE OF ALCOHOLS Common names: alkyl + alcohol IUPAC names: hydrocarbon + ol PREPARATION OF ALCOHOLS Alcohols from alkenes H2SO4, H3PO4 Markovnikov’s rule 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 Alcohols from Grignard reagents REACTIONS OF ALCOHOLS Reactions of proton in -OH Can NOT react with NaOH Dehydration reactions isomerization Primary alcohol Internal alkene 1-alkenes can NOT be prepared using the dehydration reaction Only in acidic conditions Conversion of alcohols