Chapter 14 Alcohols Phenols Ethers and begin Aldehydes

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

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

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

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

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

Alcohols 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] CH 3 -C-H O CH 3 -C-H H Ethanol (ethyl alcohol) Ethanal (acetaldehyde) Mag Biochem

Oxidation of Alcohols [O] Secondary alcohol OH ketone O CH 3 -C-CH 3 [O] CH 3 -C-CH 3 2 -Propanol (isopropyl alcohol) 2 -propanone (dimethyl ketone, “acetone”) Mag Biochem

Oxidation of Alcohols [O] Tertiary alcohols OH no reaction [O] CH 3 -C-CH 3 no product no H on the C-OH to oxidize 2 -Methyl-2 -propanol Mag Biochem

Oxidation of Ethanol in the Body l Enzymes in the liver oxidize ethanol l Aldehyde product impairs coordination l Blood alcohol over 0. 4% can be fatal. O O [O] CH 3 CH 2 OH ethyl alcohol CH 3 CH CH 3 COH acetaldhyde acetic acid Mag Biochem 2 CO 2 + H 2 O

Learning Check Ox-Red 3 Select the product for the reaction of CH 3 CH 2 OH in the following conditions: O 1) CH 3 CH=CH 2 A. 2) CO 2 + H 2 O 3) CH 3 CH 2 CH [O] _____ B. O 2, heat _____ Mag Biochem

Solution Ox-Red 3 Select the product for the reaction of CH 3 CH 2 OH in the following conditions: [O] O 3) CH 3 CH 2 CH B. O 2, heat 2) CO 2 + H 2 O A. 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 CH 3 CH 2 CH 3 B. Dimethyl ether CH 3 -O-CH 3 C. 3 -methylcyclobutanol Mag Biochem

Reduction v. Is a loss of oxygen (O) or vgain of hydrogen (H) Mag Biochem

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