Oxidation and Reduction Chapter 14 Alcohols, Phenols, Ethers (and begin Aldehydes, and Ketones) Oxidation and Reduction Mag Biochem

Classification of Alcohols Primary (1º) Secondary (2º ) Tertiary (3º) H CH3 CH3 CH3-C-OH CH3-C-OH CH3-C-OH H H CH3 1 CH3 2 CH3 3 CH3 attached attached attached to C-OH to C-OH to C-OH Mag Biochem

Learning Check Ox-Red 1 Classify the following as 1º, 2º, or 3º alcohols: OH A. CH3CH2CH2OH B. CH3-CH-CH2CH3 C. D. OH CH3-C-CH2CH3 CH3 Mag Biochem

Solution Ox-Red 1 Classify the following as 1º, 2º, or 3º alcohols: OH A. CH3CH2CH2OH 1º B. CH3-CH-CH2CH3 2º C. 2º D. OH 3º CH3-C-CH2CH3 CH3 Mag Biochem

Oxidation (OIL or LEO) Is a gain of oxygen (O) or A loss of hydrogen (H) Mag Biochem

Alcohols Alcohols aldehydes ketones 1°alcohols are oxidized to aldehydes and 2° alcohols are oxidized to ketones Alcohols 1° 2° aldehydes ketones Mag Biochem

Oxidation of Alcohols [O] Primary alcohol aldehyde OH O [O]  CH3-C-H CH3-C-H H Ethanol Ethanal (ethyl alcohol) (acetaldehyde) Mag Biochem

Oxidation of Alcohols [O] Secondary alcohol ketone OH O [O]  CH3-C-CH3 CH3-C-CH3 2-Propanol 2-propanone (isopropyl alcohol) (dimethyl ketone, “acetone”) Mag Biochem

Oxidation of Alcohols [O] Tertiary alcohols no reaction OH [O] CH3-C-CH3 no product CH3 no H on the C-OH to oxidize 2-Methyl-2-propanol Mag Biochem

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 [O]  [O]  CH3CH2OH CH3CH CH3COH 2CO2 + H2O ethyl alcohol acetaldhyde acetic acid Mag Biochem

Learning Check Ox-Red 3 Select the product for the reaction of CH3CH2CH2OH in the following conditions: O  1) CH3CH=CH2 2) CO2 + H2O 3) CH3CH2CH A. [O] _________ B. O2, heat _________ Mag Biochem

Solution Ox-Red 3 Select the product for the reaction of CH3CH2CH2OH in the following conditions: O  A. [O] 3) CH3CH2CH B. O2, heat 2) CO2 + H2O Mag Biochem

Learning Check Ox-Red 4 Write the structure of the following: A. 3-pentanol B. Dimethyl ether C. 3-methylcyclobutanol Mag Biochem

Solution Ox-Red 4 Write the structure of the following: OH | A. 3-pentanol CH3CH2CHCH2CH3 B. Dimethyl ether CH3-O-CH3 C. 3-methylcyclobutanol Mag Biochem

Reduction Is a loss of oxygen (O) or gain of hydrogen (H) Mag Biochem

Reduction Aldehydes are reduced to 1° alcohols and ketones are reduced to 2° alcohols Alcohols 1° 2° aldehydes ketones Mag Biochem