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  CH 3 — C—OH= CH 3 —COOH carboxyl group

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

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

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 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 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 C=O with –ate acidalcohol O  methyl CH 3 — C—O —CH 3 Ethanoate methyl ethanoate (IUPAC) (acetate)methyl acetate (common)

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

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

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 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 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 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 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 + CH 3 CH 2 COH + HOCH 3 O  CH 3 CH 2 COCH 3 + H 2 O

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  CH 3 COH + HOCH 3 O  B. CH 3 CO – K + + HOCH 3