Carboxylic Acids, Esters, Amines and Amides - PowerPoint PPT Presentation

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Carboxylic Acids, Esters, Amines and Amides

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Flavor/Odor. Raspberries. HCOOCH2CH3 ethyl methanoate (IUPAC) ethyl formate (common) ... compound, which is responsible for the flavor and odor of pears. ... – PowerPoint PPT presentation

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Title: Carboxylic Acids, Esters, Amines and Amides


1
Carboxylic Acids, Esters, Amines and Amides
  • Carboxylic Acids
  • Properties of Carboxylic Acids
  • Esters
  • Esterification and Hydrolysis

2
Carboxyl Group
  • Carboxylic acids contain the carboxyl group on
    carbon 1.
  • O
  • ??
  • CH3 COH CH3COOH
  • carboxyl group

3
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

4
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

5
Learning Check CA1
  • Give IUPAC and common names
  • A. CH3COOH
  • CH3
  • B. CH3CHCOOH

6
Solution CA 1
  • A. CH3COOH
  • ethanoic acid acetic acid
  • CH3
  • B. CH3CHCOOH
  • 2-methylpropanoic acid
  • ?-methylpropionic acid

7
Properties
  • Carboxylic acids are weak acids
  • CH3COOH H2O CH3COO H3O
  • Neutralized by a base
  • CH3COOH NaOH CH3COO Na H2O

8
Esters
  • In and ester, the H in the carboxyl group is
    replaced with an alkyl group
  • O
  • ??
  • CH3 CO CH3 CH3COO CH3
  • ester group

9
Esters in Plants
  • Esters give flowers and fruits their pleasant
    fragances and flavors.

10
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)

11
Some Esters and Their Names
  • Flavor/Odor
  • Raspberries
  • HCOOCH2CH3 ethyl methanoate (IUPAC)
  • ethyl formate (common)
  • Pineapples
  • CH3CH2CH2 COOCH2CH3
  • ethyl butanoate (IUPAC)
  • ethyl butyrate (common)

12
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

13
Solution CA2
  • O
  • ?? propyl
  • CH3 CO CH2CH2CH3
  • propyl ethanoate (IUPAC)
  • propyl acetate (common)

14
Learning Check CA 3
  • Draw the structure of the following compounds
  • 3-bromobutanoic acid
  • Ethyl propionoate

15
Solution CA 3
  • A. 3-bromobutanoic acid
  • Br
  • CH3CHCH2COOH
  • B. Ethyl propionoate
  • O
  • ??
  • CH3 CH2 COCH2CH3 CH3CH2COOCH2CH3

16
Esterification
  • Reaction of a carboxylic acid and alcohol
  • Acid catalyst
  • O
  • ?? H
  • CH3 COH HOCH2CH3
  • O
  • ??
  • CH3 COCH2CH3 H2O

17
Hydrolysis
  • Esters react with water and acid catalyst
  • Split into carboxylic acid and alcohol
  • O
  • ?? H
  • H COCH2CH3 H2O
  • O
  • ??
  • H COH HOCH2CH3

18
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

19
Learning Check CA4
  • Write the equation for the reaction of propionic
    acid and methyl alcohol in the presence of an
    acid catalyst.

20
Solution CA4
  • O
  • ?? H
  • CH3CH2COH HOCH3
  • O
  • ??
  • CH3CH2COCH3 H2O

21
Learning Check CA5
  • What are the organic products when methylacetate
    reacts with
  • A. Water and an acid catalyst?
  • B. KOH?

22
Solution CA5
  • A.
  • O
  • ??
  • CH3COH HOCH3
  • O
  • ??
  • B. CH3CO K HOCH3
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