Reactions of alcohols Oxidation R-X,Ether,and Ester Preparation Protection of Alcohols Synthesis The Logic of Mechanisms
Reactions of Alcohols Oxidation R-X, Ether, and Ester Preparation Protection of Alcohols Synthesis The Logic of Mechanisms
Alcohols are Synthetically Versatile TABLE 11-1 Types of Reactions of Alcohols R-OH type of reaction Product dehydration esterification R一OH alkenes R一OH R一O一( R esters oxidation R-OH ketones,aldehydes, acids tosylation R一OH R-OTs substitution R一OH R—X tosylate esters (good leaving group) halides reduction (1)form alkoxide R一OH R一H R一OH R-O一R' (2)R'X alkanes ethers
Alcohols are Synthetically Versatile
Oxidation levels of oxygen-halogen-and nitrogen- containing molecules CH2-CH2 HC-CH [O] CH:CH2OH [O] CH3CH=O CH3CO2H CH3CH3 [O] CHCH>CI CH:CHCI CH;CCls CH:CH2NH2 CH:CH=NH CH3CN Oxidation Reduction
Oxidation levels of oxygen- halogen- and nitrogencontaining molecules Reduction Oxidation C H3C H3 C H2 =CH2 HC CH [O] [O] C H3C H2OH CH3CH=O CH3C O2H C H3C H2Cl CH3CHCl2 CH3CCl3 C H3C H2N H2 CH3CH=NH CH3C N [O]
Oxidation Reduction OXIDATION H OH R一C H -OH H + H20 alkane primary alcohol aldehyde carboxylic acid no bonds to O one bond to O two bonds to O three bonds to O H OH R一CR' IO R-C-R IO R-C-R' (no further H + H2O oxidation) alkane secondary alcohol ketone no bonds to O one bond to O two bonds to O H OH R一C一 R RC 个 (usually no further oxidation) R" R" alkane tertiary alcohol no bonds to O one bond to O REDUCTION
Oxidation - Reduction
Oxidation of 2 Alcohols with Cr(VI) OH R—CH—R' NazCr2O-/H2SO4_ secondary alcohol ketone OH NazCrO1 HSO4 cyclohexanol cyclohexanone (90%6)
Oxidation of 2o Alcohols with Cr(VI)