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Aldehydes and Ketones

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IUPAC Replace the -e in the alkane name -al ... CH3CH2CH2COOH butanoic acid butyric acid. LecturePLUS Timberlake. 18. Naming Rules ... – PowerPoint PPT presentation

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Title: Aldehydes and Ketones


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 carbonyl group
  • ?
  • CH3-C-CH3

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)

3
Aldehydes as Flavorings
4
Glucose is an aldehyde
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
  • carbonyl group
  • O O
  • ? ?
  • CH3 -C-CH3 CH3-C-CH2-CH3
  • Propanone 2-Butanone
  • (Dimethyl ketone) (Ethyl methyl ketone)

6
Ketones
  • O O
  • ? ?
  • Butter flavor CH3-C-C-CH3 butanedione
  • O
  • ?
  • Clove flavor CH3-C-CH2CH2CH2CH2CH3
  • 2-heptanone

7
Fructose is a Ketone

8
Ketones as Hormones
9
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10
Learning Check AK 1
  • Classify each as an aldehyde (1), ketone (2) or
    neither(3).
  • O
  • ?
  • A. CH3CH2CCH3 B. CH3-O-CH3
  • CH3 O
  • ?
  • C. CH3-C-CH2CH D.
  • CH3

11
Solution AK 1
  • Classify each as an aldehyde (1), ketone (2) or
    neither(3).
  • O
  • ?
  • A. CH3CH2CCH3 2 B. CH3-O-CH3 3
  • CH3 O
  • ?
  • C. CH3-C-CH2CH 1 D. 2
  • CH3

12
Learning Check AK 2
  • Name the following
  • O
  • ?
  • A. CH3CH2CCH3 B.
  • O
  • ?
  • C. CH3-CH-CH2CH
  • CH2CH3

13
Solution AK 2
  • O
  • ?
  • A. CH3CH2CCH3 B.
  • 2-butanone (ethyl methyl ketone)
  • O
  • ?
  • C. CH3-CH-CH2CH
  • cyclohexanone
  • CH2CH3
  • 3-methylpentanal

14
Learning Check AK 3
  • Draw the structural formulas for each
  • A. 4-Methylpentanal
  • B. 2,3-Dichloropropanal
  • C. 3-Methyl-2-butanone

15
Solution AK 3
  • Draw the structural formulas for each
  • CH3 O
    ?
  • A. 4-Methylpentanal CH3CHCHCH2CH
  • Cl O
  • ?
  • B. 2,3-Dichloropropanal Cl-CH2CHCH

  • O
  • ?
  • C. 3-Methyl-2-butanone CH3CHCCH3
  • CH3

16
Carboxyl Group
  • Carboxylic acids contain the carboxyl group on
    carbon 1.
  • O
  • ??
  • CH3 COH CH3COOH
  • carboxyl group

17
Naming Carboxylic Acids
  • Formula IUPAC Common
  • alkan -oic acid prefix ic acid
  • HCOOH methanoic acid formic acid
  • CH3COOH ethanoic acid acetic acid
  • CH3CH2COOH propanoic acid propionic acid
  • CH3CH2CH2COOH butanoic acid butyric acid

18
Naming Rules
  • Identify longest chain
  • (IUPAC) Number carboxyl carbon as 1
  • (Common) Assign ?, ?, ? to carbon atoms adjacent
    to carboxyl carbon
  • CH3
  • CH3 CHCH2 COOH
  • IUPAC 3-methylbutanoic acid
  • Common ?-methylbutryic acid

19
Learning Check CA1
  • Give IUPAC and common names
  • A. CH3COOH
  • CH3
  • CHCOOH
  • CH3

20
Solution CA 1
  • A. CH3COOH
  • ethanoic acid acetic acid
  • CH3
  • B. CH3CHCOOH
  • 2-methylpropanoic acid
  • ?-methylpropionic acid

21
Properties
  • Carboxylic acids are weak acids
  • CH3COOH H2O CH3COO H3O
  • Neutralized by a base
  • CH3COOH NaOH CH3COO Na H2O

22
Esters
  • In and ester, the H in the carboxyl group is
    replaced with an alkyl group
  • O
  • ??
  • CH3 CO CH3 CH3COO CH3
  • ester group

23
Esters in Plants
  • Esters give flowers and fruits their pleasant
    fragances and flavors.

24
Naming Esters
  • Name the alkyl from the alcohol O-
  • Name the acid with the CO with ate
  • acid alcohol
  • O
  • ?? methyl
  • CH3 CO CH3
  • Ethanoate methyl ethanoate (IUPAC)
  • (acetate) methyl acetate (common)

25
Some Esters and Their Names
  • Flavor/Odor
  • Raspberries
  • HCOOCH2CH3 ethyl methanoate (IUPAC)
  • ethyl formate (common)
  • Pineapples
  • CH3CH2CH2 COOCH2CH3
  • ethyl butanoate (IUPAC)
  • ethyl butyrate (common)

26
Learning Check CA 2
  • Give the IUPAC and common names of the following
    compound, which is responsible for the flavor and
    odor of pears.
  • O
  • ??
  • CH3 CO CH2CH2CH3

27
Solution CA2
  • O
  • ?? propyl
  • CH3 CO CH2CH2CH3
  • propyl ethanoate (IUPAC)
  • propyl acetate (common)

28
Learning Check CA 3
  • Draw the structure of the following compounds
  • 3-bromobutanoic acid
  • Ethyl propionoate

29
Solution CA 3
  • A. 3-bromobutanoic acid
  • Br
  • CH3CHCH2COOH
  • B. Ethyl propionoate
  • O
  • ??
  • CH3 CH2 COCH2CH3 CH3CH2COOCH2CH3

30
Esterification
  • Reaction of a carboxylic acid and alcohol
  • Acid catalyst
  • O
  • ?? H
  • CH3 COH HOCH2CH3
  • O
  • ??
  • CH3 COCH2CH3 H2O

31
Hydrolysis
  • Esters react with water and acid catalyst
  • Split into carboxylic acid and alcohol
  • O
  • ?? H
  • H COCH2CH3 H2O
  • O
  • ??
  • H COH HOCH2CH3

32
Saponification
  • Esters react with a bases
  • Produce the salt of the carboxylic acid and
    alcohol
  • O
  • ??
  • CH3COCH2CH3 NaOH
  • O
  • ??
  • CH3CO Na HOCH2CH3
  • salt of carboxylic acid

33
Learning Check CA4
  • Write the equation for the reaction of propionic
    acid and methyl alcohol in the presence of an
    acid catalyst.

34
Solution CA4
  • O
  • ?? H
  • CH3CH2COH HOCH3
  • O
  • ??
  • CH3CH2COCH3 H2O

35
Learning Check CA5
  • What are the organic products when methylacetate
    reacts with
  • A. Water and an acid catalyst?
  • B. KOH?

36
Solution CA5
  • A.
  • O
  • ??
  • CH3COH HOCH3
  • O
  • ??
  • B. CH3CO K HOCH3
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