1 Chapter 13 Organic Compounds with Oxygen and Sulfur 13.4 Aldehydes and Ketones

2 Carbonyl Group in Aldehydes and Ketones A carbonyl group in an aldehyde is attached to at least one H atom. in a ketone is attached to two carbon groups.

3 Naming Aldehydes An aldehyde has an IUPAC name in which the -e in the alkane name is changed to –al. has a common name for the first four aldehydes that use the prefixes: form (1C), acet (2C), propion (3C), and butyr (4C), followed by aldehyde. O O O ║ ║ ║ H─C─H CH 3 ─C─HCH 3 ─CH 2 ─C─H methanal ethanalpropanal ( form aldehyde) ( acet aldehyde)( propion aldehyde)

4 Naming Aldehydes

5 Aldehydes in Flavorings Several naturally occurring aldehydes are used as flavorings for foods and fragrances. Benzaldehyde (almonds) Cinnamaldehyde (cinnamon)

6 Naming Ketones In naming ketones as IUPAC, the -e in the alkane name is replaced with –one. With a common name, the alkyl groups attached to the carbonyl group are named alphabetically followed by ketone. O O ║ ║ CH 3 ─C─CH 3 CH 3 ─C─CH 2 ─CH 3 propanone 2-butanone (dimethyl ketone) (ethyl methyl ketone)

7 Ketones in Common Use Nail polish remover, solvent Propanone, Dimethylketone, Acetone Butter flavoring

8 Classify each as 1) aldehyde or 2) ketone. O O || || A. CH 3 —CH 2 —C—CH 3 B. CH 3 —C—H CH 3 O | || C. CH 3 —C—CH 2 —C—H D. | CH 3 Learning Check

9 A. 2 ketone B. 1 aldehyde C. 1 aldehyde D. 2 ketone Solution

10 Learning Check Classify each as an 1) aldehyde2) ketone3) alcohol or 4) ether. O ║ A. CH 3 ─CH 2 ─C─CH 3 B. CH 3 ─O─CH 3 CH 3 O OH │ ║ │ C. CH 3 ─C─CH 2 ─C─HD. CH 3 ─CH ─CH 3 │ CH 3

11 Solution O ║ A. CH 3 ─CH 2 ─C─CH 3 B. CH 3 ─O─CH 3 2) ketone 4) ether CH 3 O OH │ ║ │ C. CH 3 ─C─CH 2 ─C─HD. CH 3 ─CH─CH 3 │ CH 3 1) aldehyde 3) alcohol

12 Learning Check Name each of the following. O ║ 1. CH 3 ─CH 2 ─CH 2 ─CH 2 ─C─H O ║ 2. Cl─CH 2 ─CH 2 ─C─H O ║ 3. CH 3 ─CH 2 ─C─CH 3

13 Solution Name each of the following: O ║ 1. CH 3 ─CH 2 ─CH 2 ─CH 2 ─C─H pentanal O ║ 2. Cl─CH 2 ─CH 2 ─C─H3-chloropropanal O ║ 3. CH 3 ─CH 2 ─C─CH 3 2-butanone; ethyl methyl ketone

14 Name the following compounds. O || A. CH 3 —CH 2 —CH 2 —C—CH 3 B. CH 3 O | || C. CH 3 —C—CH 2 —C—H | CH 3 Learning Check

15 A. 2-pentanone; methyl propyl ketone B. cyclohexanone C,3,3-dimethylbutanal Solution

16 Learning Check Draw the structural formulas for each: A. 4-methylpentanal B. 2,3-dichloropropanal C. 3-methyl-2-butanone

17 Solution Draw the structural formulas for each: CH 3 O │ ║ A. 4-methylpentanalCH 3 ─CH─CH 2 ─CH 2 ─C─H Cl O │ ║ B. 2,3-dichloropropanal Cl─CH 2 ─CH─C─H CH 3 O │ ║ C. 3-methyl-2-butanoneCH 3 ─CH─C─CH 3