Experiment 12

Carboxylic Acids and Acid Derivatives

1. Write the chemical reactions involved in tests A-F.
a. Solubility of Carboxylic Acids in 5% NaHCO3.
Glacial acetic acid

+
Benzoic Acid

+ H2O + CO2(g)

+
b. Test for Acetic acid

+ H2O + CO2(g)

+ NaOH Fe(OH)2(CH3COO-)
c. Test for Benzoic Acid

+ NH4OH
d. Formation of Esters
From carboxylic acids

+
From acyl halides

+ H2O

+
e. Hydroxamic Test

+ H2O

f.

+
Hydrolysis of Acid Derivatives
Acetic anhydride

CH3CONHOH +

(CH3CO)2O + H2O
Esters
+ NaOH

Amines
+ NaOH

+ NH3

2. Why would acyl halides yield higher amides compared to carboxylic acids or esters on reactions with
ammonia?
Acy l halides have higher yield due to the fact that it is much more unstable and therefore
much reactive than carboxylic acids and esters. The leaving group (X-) causes acyl halides to
be more reactive than carboxylic acids and esters.
3. Why should excess alkali be avoided in the test for acetic and benzoic acid using FeCl3 solution?
It should be avoided because the excess OH- would react with the Fe3+ forming a red orange
complex [Fe(OH)3]. The Fe3+ would be less available for the production of the red complex
Fe(OH)2(CH3COO) (with acetic acid) or the flesh colored precipitate Fe(C6H5COO) (with
benzoic acid), and thus would yield to inaccurate results.
Reference:
http://chemistry2.csudh.edu/rpendarvis/carboxder.html
http://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/crbacid2.htm