Chapter 13 Organic Compounds with Oxygen and Sulfur

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Chapter 13 Organic Compounds with Oxygen and Sulfur 13. 4 Aldehydes and Ketones 1

Chapter 13 Organic Compounds with Oxygen and Sulfur 13. 4 Aldehydes and Ketones 1

Carbonyl Group in Aldehydes and Ketones A carbonyl group • in an aldehyde is

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. 2

Naming Aldehydes An aldehyde • has an IUPAC name in which the -e in

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 (1 C), acet (2 C), propion (3 C), and butyr (4 C), followed by aldehyde. O ║ H─C─H O ║ CH 3─CH 2─C─H methanal (formaldehyde) ethanal (acetaldehyde) propanal (propionaldehyde) 3

Naming Aldehydes 4

Naming Aldehydes 4

Aldehydes in Flavorings Several naturally occurring aldehydes are used as flavorings for foods and

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

Naming Ketones In naming ketones • as IUPAC, the -e in the alkane name

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─C─CH 2─CH 3 propanone 2 -butanone (dimethyl ketone) (ethyl methyl ketone) 6

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

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

Learning Check Classify each as 1) aldehyde or 2) ketone. O O || ||

Learning Check 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 | CH 3 D. 8

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

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

Learning Check Classify each as an 1) aldehyde 2) ketone O ║ A. CH

Learning Check Classify each as an 1) aldehyde 2) ketone O ║ A. CH 3─CH 2─C─CH 3 O │ ║ C. CH 3─C─CH 2─C─H │ CH 3 3) alcohol or 4) ether. B. CH 3─O─CH 3 OH │ D. CH 3─CH 3 10

Solution O ║ A. CH 3─CH 2─C─CH 3 2) ketone CH 3 O │

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

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

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

Solution Name each of the following: O ║ 1. CH 3─CH 2─CH 2─C─H O

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

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

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

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

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

Learning Check Draw the structural formulas for each: A. 4 -methylpentanal B. 2, 3

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

Solution Draw the structural formulas for each: CH 3 O │ ║ A. 4

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