Beruflich Dokumente
Kultur Dokumente
I.
INTRODUCTION
A. Acyl Compounds
,where G is a halogen
R = alkyl or aryl
R
OH
+
R
:Base
+
R
OH
H-Base
OH
R
acid halide
acid anhydride
ester
H3C
NH2
amide
O
H
H 3C
H3C
R1
substituted amides
Nitriles, R - CN, though not acyl compounds, are considered as
carboxylic acid functional derivatives because they are readily hydrolyzed
to carboxylic acids.
Nucleophilic addition to the carbonyl group is less likely in acyl
compounds than in aldehydes and ketones. The characteristic reaction of
acyl compounds is nucleophilic acyl substitution:
+
R1
:Nu
H3C
G
Nu
+ G-
H3C
Nu
O
H2C
OH
H2 C
C R
O
HC
OH
HC
C R1
O
H2C
OH
H2 C
glycerol
R2
triacylglycerol
O
H2 C
C R
O
HC
H2 C
O
O
C R1
O
C R2
H2C
OH
HC
OH
3NaOH
+
R
H2C
O
-
O Na R1
O Na R2
O Na
OH
soaps
CH3(CH2)10CH2OH
S
O
lauryl alcohol
II.
O
OH
S
O
OBJECTIVES
1. To observe the general properties of carboxylic acids.
2. To compare the acidity of carboxylic acids and phenols.
3. To verify experimentally the interconversion among acyl compounds.
O Na
III.
PROCEDURE
5. Heat the mixture while swirling over a small flame. Continue for about
15 minutes or until the mixture is viscous
6. Cool the mixture
7. Add 50 mL saturated NaCl solution while stirring
8. Suction filter the product
9. Wash the soap twice with 15 mL ice-cold distilled water
10. Allow to dry
D. Comparison of soaps and detergents
Dissolve one spatula tip of soap sample in 30 mL of warm distilled water. Do
the same with a sample of detergent. Use mixtures formed for the following
tests.
1. Hydrolysis
Test the mixture with red and blue litmus paper
2. Reaction with acid
a. Place 5 mL of the sample in a test tube
b. Add 10 mL 0.5 M HCl
c. Shake to mix. Observe
3. Reaction with soft and hard water
a. Place 5 mL of 0.02 M NaCl (soft water) in a test tube
b. Add 15 drops of the sample
c. Repeat with 0.02 M CaCl2 (hard water)
4. Emulsifying action
a. Place 8 drops of kerosene in a test tube
b. Add 5 mL sample
c. Shake the tube vigorously for three minutes
d. Allow to stand for 5 minutes. Run water blank.
IV.
QUESTIONS
1. Explain the difference in the solubility of benzoic acid and sodium
benzoate in water. Which of the two would you predict to be more
soluble in CHCl3? Explain.
2. Based on the results in Part A.2, what can be said about the relative
acidities of phenols and carboxylic acids? Arrange the following
compound types in order of increasing acidity: carboxylic acid, alcohol,
phenol and water.
3. Based on the results in Part B, arrange the following compound types
in the order of decreasing hydrolysis rate: acid halides, acid