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Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones Oxidation and Reduction Timberlake LesturePLUS 1999 1 Classification of Alcohols Primary (1º) H Secondary (2º ) CH3 CH3-C-OH CH3-C-OH H H 1 CH3 attached to C-OH 2 CH3 attached to C-OH Timberlake LesturePLUS 1999 Tertiary (3º) CH3 CH3-C-OH CH3 3 CH3 attached to C-OH 2 Learning Check Ox-Red 1 Classify the following as 1º, 2º, or 3º alcohols: OH A. CH3CH2CH2OH C. OH B. CH3-CH-CH2CH3 D. OH CH3-C-CH2CH3 CH3 Timberlake LesturePLUS 1999 3 Solution Ox-Red 1 Classify the following as 1º, 2º, or 3º alcohols: OH A. CH3CH3CH2OH 1º C. OH 2º B. CH3-CH-CH2CH3 2º D. OH 3º CH3-C-CH2CH3 CH3 Timberlake LesturePLUS 1999 4 Oxidation Is a gain of oxygen (O) or A loss of hydrogen (H) Timberlake LesturePLUS 1999 5 Alcohols 1°alcohols are oxidized to aldehydes and 2° alcohols are oxidized to ketones Alcohols 1° 2° aldehydes ketones Timberlake LesturePLUS 1999 6 Oxidation of Alcohols [O] Primary alcohol OH [O] CH3-C-H aldehyde O CH3-C-H H Ethanol (ethyl alcohol) Ethanal (acetaldehyde) Timberlake LesturePLUS 1999 7 Oxidation of Alcohols [O] Secondary alcohol OH [O] CH3-C-CH3 2-Propanol (isopropyl alcohol) ketone O CH3-C-CH3 2-propanone (dimethyl ketone, “acetone”) Timberlake LesturePLUS 1999 8 Oxidation of Alcohols [O] Tertiary alcohols OH no reaction [O] CH3-C-CH3 CH3 no product no H on the C-OH to oxidize 2-Methyl-2-propanol Timberlake LesturePLUS 1999 9 Oxidation of Ethanol in the Body Enzymes in the liver oxidize ethanol Aldehyde product impairs coordination Blood alcohol over 0.4% can be fatal. O O CH3CH2OH CH3CH CH3COH 2CO2 + H2O ethyl alcohol acetaldhyde acetic acid Timberlake LesturePLUS 1999 10 Learning Check Ox-Red 3 Select the product for the reaction of CH3CH2CH2OH in the following conditions: O 1) CH3CH=CH2 A. H+, heat B. 2) CO2 + H2O 3) CH3CH2CH _________ [O] _________ C. O2, heat _________ Timberlake LesturePLUS 1999 11 Solution Ox-Red 3 Select the product for the reaction of CH3CH2CH2OH in the following conditions: A. H+, heat B. [O] C. O2, heat 1) CH3CH=CH2 O 3) CH3CH2CH 2) CO2 + H2O Timberlake LesturePLUS 1999 12 Learning Check Ox-Red 4 Write the structure of the following: A. 3-pentanol B. Dimethyl ether C. 3-methylcyclobutanol Timberlake LesturePLUS 1999 13 Solution Ox-Red 4 Write the structure of the following: OH | A. 3-pentanol CH3CH2CHCH2CH3 B. Dimethyl ether CH3-O-CH3 CH 3 C. 3-methylcyclobutanol Timberlake LesturePLUS 1999 OH14 Reduction Is a loss of oxygen (O) or gain of hydrogen (H) Timberlake LesturePLUS 1999 15 Reduction Aldehydes are reduced to 1° alcohols and ketones are reduced to 2° alcohols Alcohols 1° aldehydes 2° ketones Timberlake LesturePLUS 1999 16