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

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Presentation on theme: "1 Carboxylic Acids, Esters, Amines and Amides Carboxylic Acids Properties of Carboxylic Acids Esters Esterification and Hydrolysis."— Presentation transcript:

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

2 2 Carboxyl Group Carboxylic acids contain the carboxyl group on carbon 1. O  CH 3 — C—OH= CH 3 —COOH carboxyl group

3 3 Naming Carboxylic Acids Formula IUPAC Common alkan -oic acid prefix – ic acid HCOOH methanoic acid formic acid CH 3 COOH ethanoic acid acetic acid CH 3 CH 2 COOH propanoic acid propionic acid CH 3 CH 2 CH 2 COOH butanoic acid butyric acid

4 4 Naming Rules Identify longest chain (IUPAC) Number carboxyl carbon as 1 (Common) Assign , ,  to carbon atoms adjacent to carboxyl carbon CH 3 | CH 3 — CH—CH 2 —COOH IUPAC 3-methylbutanoic acid Common  -methylbutryic acid

5 5 Learning Check CA1 Give IUPAC and common names: A. CH 3 COOH CH 3 | B. CH 3 CHCOOH

6 6 Solution CA 1 A. CH 3 COOH ethanoic acid; acetic acid CH 3 | B. CH 3 CHCOOH 2-methylpropanoic acid;  -methylpropionic acid

7 7 Properties Carboxylic acids are weak acids CH 3 COOH + H 2 O CH 3 COO – + H 3 O + Neutralized by a base CH 3 COOH + NaOH CH 3 COO – Na + + H 2 O

8 8 Esters In and ester, the H in the carboxyl group is replaced with an alkyl group O  CH 3 — C—O —CH 3 = CH 3 —COO —CH 3 ester group

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

10 10 Naming Esters Name the alkyl from the alcohol –O- Name the acid with the C=O with –ate acidalcohol O  methyl CH 3 — C—O —CH 3 Ethanoate methyl ethanoate (IUPAC) (acetate)methyl acetate (common)

11 11 Some Esters and Their Names Flavor/Odor Raspberries HCOOCH 2 CH 3 ethyl methanoate (IUPAC) ethyl formate (common) Pineapples CH 3 CH 2 CH 2 COOCH 2 CH 3 ethyl butanoate (IUPAC) ethyl butyrate (common)

12 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  CH 3 — C—O —CH 2 CH 2 CH 3

13 13 Solution CA2 O  propyl CH 3 — C—O —CH 2 CH 2 CH 3 propyl ethanoate (IUPAC) propyl acetate (common)

14 14 Learning Check CA 3 Draw the structure of the following compounds: A.3-bromobutanoic acid B.Ethyl propionoate

15 15 Solution CA 3 A. 3-bromobutanoic acid Br | CH 3 CHCH 2 COOH B.Ethyl propionoate O  CH 3 CH 2 COCH 2 CH 3 CH 3 CH 2 COOCH 2 CH 3

16 16 Esterification Reaction of a carboxylic acid and alcohol Acid catalyst O  H + CH 3 — C—OH + HO—CH 2 CH 3 O  CH 3 — C—O—CH 2 CH 3 + H 2 O

17 17 Hydrolysis Esters react with water and acid catalyst Split into carboxylic acid and alcohol O  H + H — C—O—CH 2 CH 3 + H 2 O O  H — C—OH + HO—CH 2 CH 3

18 18 Saponification Esters react with a bases Produce the salt of the carboxylic acid and alcohol O  CH 3 C—OCH 2 CH 3 + NaOH O  CH 3 C—O – Na + + HOCH 2 CH 3 salt of carboxylic acid

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

20 20 Solution CA4 O  H + CH 3 CH 2 COH + HOCH 3 O  CH 3 CH 2 COCH 3 + H 2 O

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

22 22 Solution CA5 A. O  CH 3 COH + HOCH 3 O  B. CH 3 CO – K + + HOCH 3


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