Chapter 12 Alcohols, Phenols, Ethers, Aldehydes, and Ketones Aldehydes and Ketones LecturePLUS Timberlake 1 Aldehydes and Ketones In an aldehyde, an H atom is attached to a carbonyl group O carbonyl group CH3-C-H In a ketone, two carbon groups are attached to a carbonyl group O CH3-C-CH3 carbonyl group LecturePLUS Timberlake 2 Naming Aldehydes IUPAC Replace the -e in the alkane name -al Common Add aldehyde to the prefixes form (1C), acet (2C), propion(3), and butry(4C) O O O H-C-H CH3-C-H CH3CH2C-H methanal ethanal propanal (formaldehyde) (acetaldehyde) (propionaldehyde) LecturePLUS Timberlake 3 Aldehydes as Flavorings O O CH CH O CH=CH CH HO OCH3 Benzaldehyde (almonds) Vanillin (vanilla beans) LecturePLUS Timberlake Cinnamaldehyde (cinnamon) 4 Glucose is an aldehyde O H C H C OH HO C H H C OH H C OH CH2OH glucose LecturePLUS Timberlake 5 Naming Ketones In the IUPAC name, the -e in the alkane name is replaced with -one In the common name, add the word ketone after naming the alkyl groups attached to the O carbonyl group O CH3 -C-CH3 O CH3-C-CH2-CH3 Propanone 2-Butanone Cyclohexanone (Dimethyl ketone) (Ethyl methyl ketone) LecturePLUS Timberlake 6 Ketones OO Butter flavor CH3-C-C-CH3 O butanedione Clove flavor CH3-C-CH2CH2CH2CH2CH3 2-heptanone LecturePLUS Timberlake 7 Fructose is a Ketone CH 2OH C HO O C H H C OH H C OH CH 2OH D-Fructose LecturePLUS Timberlake 8 Ketones as Hormones CH2OH O CH3 O OH CH3 O Cortisone LecturePLUS Timberlake 9 Learning Check AK 1 Classify each as an aldehyde (1), ketone (2) or neither(3). O A. CH3CH2CCH3 CH3 B. CH3-O-CH3 O O C. CH3-C-CH2CH D. CH3 LecturePLUS Timberlake 10 Solution AK 1 Classify each as an aldehyde (1), ketone (2) or neither(3). O A. CH3CH2CCH3 CH3 2 O O C. CH3-C-CH2CH 1 CH3 B. CH3-O-CH3 3 D. LecturePLUS Timberlake 2 11 Learning Check AK 2 Name the following O O A. CH3CH2CCH3 CH3 B. O C. CH3-C-CH2CH CH3 LecturePLUS Timberlake 12 Solution AK 2 O O A. CH3CH2CCH3 B. 2-butanone (ethyl methyl ketone) CH3 O C. CH3-C-CH2CH CH3 2,2-dimethylbutanal LecturePLUS Timberlake cyclohexanone 13 Learning Check AK 3 Draw the structural formulas for each: A. 3-Methylpentanal B. 2,3-Dichloropropanal C. 3-Methyl-2-butanone LecturePLUS Timberlake 14 Solution AK 3 Draw the structural formulas for each: CH3 A. 3-Methylpentanal O CH3CHCHCH2CH Br O B. 2,3-Dichloropropanal Br-CH2CHCH O C. 3-Methyl-2-butanone CH3CHCCH3 LecturePLUS Timberlake CH3 15