CHM2123 Problem Set #9 Saponification of Esters/Soaps

Posted November 27th, 2015

1. In part A of the experiment, you are asked to perform a titration.

Assuming that you perform the experiment as described, and
22.00 mL H2SO4 are required to reach the equivalence point,
determine the concentration of NaOH in your alcoholic solution.
(2 points)
solution volume = 30 mL NaOH/EtOH
at equivalence point, moles of base are equal to moles of acid.
0.022 L x 0.25 mol/L = 0.0055 mol H2SO4 x (2 mol NaOH/1 mol
H2SO4) = 0.011 mol NaOH
[NaOH] = 0.011 mol/0.030 L = 0.367 M NaOH

2. In another experiment to determine the molar mass of an ester,

a student dissolves 450 mg of an unknown ester into 50 mL
alcoholic NaOH. After the hydrolysis reaction was complete, the
mixture required 19 mL of sulfuric acid, 0.5N, to be neutralized.
When the concentration of the starting material was determined,
20 mL of the same NaOH solution was neutralized with exactly
10.00 mL of 0.5 N H2SO4.
a) The acid concentration is defined in Normality instead of
Molarity. What is the difference between molarity and
normality? (1 point)
Normality is the equivalent concentration of H+ or OH ions in
solution, whereas molarity is simply the concentration of the
molecule in solution.
b) Determine the concentration of NaOH used in this reaction. (1
point)

c) Determine the concentration of unreacted NaOH after ester

hydrolysis. (1 point)

d) Determine the molar mass of the ester. (1 point)

e) Knowing that the ester is monobasic, absorbs strongly under

UV light, displays a weak band located at 3078 cm-1 in the IR
spectrum, and displays no singlet peaks in the 1H NMR,
determine its structure. (1 point) (There are two possibilities)

3. Sodium laureth sulfate or sodium stearate are key ingredients in

many soaps. How do these molecules work to remove a stain,
such as pen ink, from your shirt? How is this different from
bleach? (2 points)
Sodium laureth sulfate and sodium stearate are surfactants
found in soaps and detergents. At a certain concentration of
surfactant, the molecules will self-assemble to form a micelle
via electrostatic interactions. The exterior of the micelle is
composed of hydrophillic, water-loving groups, and the inside
of the micelle is composed of lipophilic, oil-loving tails. With a
bit of force and friction, the ink dissolves into the emulsion of the
micelle, and the stain is lifted away.

O
O
Na

Bleach is an oxidizing agent that induces a chemical reaction

to remove the stain, whereas micelles simply cage and
physically transport the stain off of the clothing.

4. Based on the observations you will be performing in this

experiment, how could you determine if the tap water in the MRN
laboratory is hard water? (1 point)
In step 3 of Preparation of a hard soap, you place a small
amount of hard soap in a test tube with distilled water and
shake. The distilled water will produce many suds.
Compare this to the Marion tap water. If the water is soft, it
should still easily produce suds. On the other hand, if the tap
water is hard, creating suds will be comparatively more
difficult.