Aldehydes and Ketones In an aldehyde, a carbon group and an H atom is attached to a carbonyl group O CH3 - C - H carbonyl group carbonyl group always joined to at least one hydrogen (meaning it is always on the end!) Aldehydes and Ketones In a ketone, two carbon groups are attached to a carbonyl group O carbonyl group CH3 - C - CH3 carbon of the carbonyl group is joined to two other carbons (meaning it is never on the end) Naming Aldehydes IUPAC Replace the -e in the alkane name with –al Common Add aldehyde to the prefixes form (1C), acet (2C), propion(3), and butry(4C) O H-C-H methanal O CH3-C-H ethanal O CH3CH2C-H propanal (formaldehyde) (acetaldehyde) (propionaldehyde) Methanal common name: formaldehyde 40% in water is formalin, a preservative Aldehydes as Flavorings O O CH CH O CH=CH CH HO OCH3 Benzaldehyde (almonds) Vanillin (vanilla beans) Cinnamaldehyde (cinnamon) Glucose is an aldehyde O H C H C OH HO C H H C OH H C OH CH 2OH glucose 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) Propanone Common name: acetone nail-polish remover miscible with water in all proportions Ketones O O Butter flavor CH3-C-C-CH3 O butanedione Clove flavor CH3-C-CH2CH2CH2CH2CH3 2-heptanone Fructose is a Ketone CH 2OH C HO O C H H C OH H C OH CH 2OH D-Fructose Ketones as Hormones CH2OH O CH3 O OH CH3 O Cortisone Aldehydes and Ketones Neither can form intermolecular hydrogen bonds, thus a much lower b.p. than corresponding alcohols Learning Check Classify each as an aldehyde (1), ketone (2) or neither(3). O A. CH3CH2CCH3 CH3 O O C. CH3-C-CH2CH CH3 B. CH3-O-CH3 D. Solution Classify each as an aldehyde (1), ketone (2) or neither(3). O A. CH3CH2CCH3 CH3 2 O C. CH3-C-CH2CH 1 CH3 B. CH3-O-CH3 3 D. O 2 Learning Check Name the following O O A. CH3CH2CCH3 CH3 O C. CH3-C-CH2CH CH3 B. Solution O O A. CH3CH2CCH3 B. 2-butanone (ethyl methyl ketone) CH3 O C. CH3-C-CH2CH CH3 3,3-dimethylbutanal cyclohexanone Learning Check Draw the structural formulas for each: A. 3-Methylpentanal B. 2,3-Dichloropropanal C. 3-Methyl-2-butanone Solution Draw the structural formulas for each: CH3 O A. 3-Methylpentanal B. 2,3-Dichloropropanal CH3CH2CHCH2CH Cl O Cl-CH2CHCH C. 3-Methyl-2-butanone O CH3CHCCH3 CH