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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 CH3─C─H CH3─CH2─C─H
methanal ethanal propanal
(formaldehyde) (acetaldehyde) (propionaldehyde)
4
Naming Aldehydes
5
Aldehydes in Flavorings
Several naturally occurring aldehydes are used as flavorings for foods and fragrances.
H
O
C
H
O
CCH=CH
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
║ ║
CH3 ─C─CH3 CH3─C─CH2─CH3 propanone 2-butanone
(dimethyl ketone) (ethyl methyl ketone)
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Ketones in Common Use
Nail polish remover, solvent
Propanone, Dimethylketone, Acetone
Butter flavoring
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Classify each as 1) aldehyde or 2) ketone. O O
|| ||A. CH3—CH2—C—CH3 B. CH3—C—H
CH3 O | ||
C. CH3—C—CH2—C—H D. | CH3
Learning Check
O
9
A. 2 ketone
B. 1 aldehyde
C. 1 aldehyde
D. 2 ketone
Solution
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Learning Check
Classify each as an 1) aldehyde 2) ketone 3) alcohol or 4) ether. O ║ A. CH3─CH2─C─CH3 B. CH3─O─CH3
CH3 O OH
│ ║ │C. CH3─C─CH2─C─H D. CH3─CH ─CH3
│ CH3
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Solution
O ║A. CH3─CH2─C─CH3 B. CH3─O─CH3
2) ketone 4) ether CH3 O OH
│ ║ │C. CH3─C─CH2─C─H D. CH3─CH─CH3
│ CH3
1) aldehyde 3) alcohol
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Learning Check
Name each of the following. O ║1. CH3─CH2─CH2─CH2─C─H
O
║ 2. Cl─CH2─CH2─C─H O ║ 3. CH3─CH2─C─CH3
13
Solution
Name each of the following: O ║1. CH3─CH2─CH2─CH2─C─H pentanal
O
║ 2. Cl─CH2─CH2─C─H 3-chloropropanal O ║ 3. CH3─CH2─C─CH3 2-butanone;
ethyl methyl ketone
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Name the following compounds. O
||A. CH3—CH2—CH2—C—CH3 B.
CH3 O | ||
C. CH3—C—CH2—C—H | CH3
Learning Check
O
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A. 2-pentanone; methyl propyl ketone
B. cyclohexanone
C, 3,3-dimethylbutanal
Solution
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Learning Check
Draw the structural formulas for each:
A. 4-methylpentanal
B. 2,3-dichloropropanal
C. 3-methyl-2-butanone
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Solution
Draw the structural formulas for each: CH3 O
│ ║ A. 4-methylpentanal CH3─CH─CH2─CH2─C─H
Cl O │ ║
B. 2,3-dichloropropanal Cl─CH2─CH─C─H
CH3 O │ ║
C. 3-methyl-2-butanone CH3─CH─C─CH3