ORGANIC CHEMISTRY Chapter 12 12.4 Oxidation of alcohols Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 12.4 Oxidation of Alcohols
ORGANIC CHEMISTRY Chapter 12 12.4A Oxidation of Primary Alcohols to Aldehyd y des RCHOH RCHO o Primary alcohols can be oxidized to aldehydes and carboxylic acids [O] RCH2OH—RCHO—RCO2H 1 Alcohol Aldehyde Carboxylic acid o Aldehydes are more easily oxidized than primar alcohoIs Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 12.4A Oxidation of Primary Alcohols to Aldehydes RCH2OH RCHO Primary alcohols can be oxidized to aldehydes and carboxylic acids. RCH2OH RCHO RCO2H [O] [O] 1°Alcohol Aldehyde Carboxylic acid Aldehydes are more easily oxidized than primary alcohols
ORGANIC CHEMISTRY Chapter 12 o An excellent reagent for oxidation of primary alcohols to aldehydes is pyridinium chlorochromate(PCC) CH2OH PCC CHO CHoCI PCC (Pyridinium chlorochromate) CrO3 Hcl N一H CrOr Cl ridin PCC Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 An excellent reagent for oxidation of primary alcohols to aldehydes is pyridinium chlorochromate (PCC). CH2OH CHO 82% CH2Cl2 PCC PCC (Pyridinium chlorochromate) CrO3 + HCl + N N H pyridin CrO3Cl PCC
ORGANIC CHEMISTRY Chapter 12 12. 4B Oxidation of Primary alcohols to Carboxylic Acids RCHOH RCOH o Primary alcohols can be oxidized to carboxylic acids y potassium permanganate OH R-CH2OH+ KMnOA H2O,△ RCO2 K+ MnO2 H3O RCO2H Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 12.4B Oxidation of Primary Alcohols to Carboxylic Acids RCH2OH RCO2H Primary alcohols can be oxidized to carboxylic acids by potassium permanganate. R CH2OH + KMnO4 OH H2O, RCO2 K + MnO2 H3O RCO2H
ORGANIC CHEMISTRY Chapter 12 12. 4C Oxidation of Secondary alcohols to Ketones OH R-CH-R R-C-R o Secondary alcohols can be oxidized to ketones OH [O] R-CH-R R-C-R 2° Alcohol Ketone 9 Oxidizing agent o H, CrO4(crO3/h,sO4, Na, cr,o, H,SO4) o CrO3/H2SO4, H2O-acetone- Jones'reagent °KMnO Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 12.4C Oxidation of Secondary Alcohols to Ketones R CH R' OH R C R' O Secondary alcohols can be oxidized to ketones. R CH R' OH R C R' O [O] 2°Alcohol Ketone Oxidizing agent: H2CrO4 (CrO3 /H2SO4 ,Na2Cr2O7/ H2SO4) CrO3/ H2SO4 , H2O-acetone — Jones’ reagent KMnO4