Timberlake LesturePLUS Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones Oxidation and Reduction

Timberlake LesturePLUS Classification of Alcohols Primary (1º)Secondary (2º )Tertiary (3º) H CH 3 CH 3 CH 3 -C-OHCH 3 -C-OHCH 3 -C-OH H H CH 3 1 CH 3 2 CH 3 3 CH 3 attachedattachedattached to C-OH to C-OH to C-OH

Timberlake LesturePLUS Learning Check Ox-Red 1 Classify the following as 1º, 2º, or 3º alcohols: OH A. CH 3 CH 2 CH 2 OHB. CH 3 -CH-CH 2 CH 3 C. D. OH CH 3 -C-CH 2 CH 3 CH 3

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

Timberlake LesturePLUS Oxidation  Is a gain of oxygen (O) or  A loss of hydrogen (H)

Timberlake LesturePLUS Alcohols 1°alcohols are oxidized to aldehydes and 2° alcohols are oxidized to ketones Alcohols 1° 2° aldehydes ketones

Timberlake LesturePLUS Oxidation of Alcohols [O] Primary alcoholaldehyde OH O [O]  CH 3 -C-H CH 3 -C-H H EthanolEthanal (ethyl alcohol)(acetaldehyde)

Timberlake LesturePLUS Oxidation of Alcohols [O] Secondary alcoholketone OH O [O]  CH 3 -C-CH 3 CH 3 -C-CH 3 2-Propanol2-propanone (isopropyl alcohol)(dimethyl ketone, “acetone”)

Timberlake LesturePLUS Oxidation of Alcohols [O] Tertiary alcoholsno reaction OH[O] CH 3 -C-CH 3 no product CH 3 no H on the C-OH to oxidize 2-Methyl-2-propanol

Timberlake LesturePLUS 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]  CH 3 CH 2 OH CH 3 CH CH 3 COH 2CO 2 + H 2 O ethylalcohol acetaldhyde acetic acid

Timberlake LesturePLUS Learning Check Ox-Red 3 Select the product for the reaction of CH 3 CH 2 CH 2 OH in the following conditions: O  1) CH 3 CH=CH 2 2) CO 2 + H 2 O 3) CH 3 CH 2 CH A. H +, heat_________ B. [O]_________ C. O 2, heat_________

Timberlake LesturePLUS Solution Ox-Red 3 Select the product for the reaction of CH 3 CH 2 CH 2 OH in the following conditions: A. H +, heat 1) CH 3 CH=CH 2 O  B. [O] 3) CH 3 CH 2 CH C. O 2, heat 2) CO 2 + H 2 O

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

Timberlake LesturePLUS Solution Ox-Red 4 Write the structure of the following: OH | A. 3-pentanolCH 3 CH 2 CHCH 2 CH 3 B. Dimethyl ether CH 3 -O-CH 3 C. 3-methylcyclobutanol

Timberlake LesturePLUS Reduction  Is a loss of oxygen (O) or  gain of hydrogen (H)

Timberlake LesturePLUS Reduction Aldehydes are reduced to 1° alcohols and ketones are reduced to 2° alcohols Alcohols 1°2° aldehydes ketones