EXERCISE 1

1. 68% of salicylic acid was extracted from 100 mL DCM using 30 mL of water. Calculate the 𝐾 𝐷𝐶𝑀 .
𝑊𝑎𝑡𝑒𝑟
2. Using liquid-liquid extraction, 5.0 grams of compound M in 80 mL water was extracted twice using
10 mL ethyl acetate. (Kd=15.2)
a. Calculate the mass of compound M remained in water.
b. Determine the % efficiency of two step extraction over single step using 20 mL ethyl acetate.

EXERCISE 2

1. Complete the following table. Given the following errors, state the effect (increase, decrease or no
effect) on the % recovery and on the purity of the sample. Also write a phrase or a sentence to
explain your answer.

2. The following impurities are present on the crude compound AUBREY.

Impurities Solubility at Room Temp (g/10 mL) Solubility at 100 oC (g/10mL)

KARA 0.00051 0.025
MIA 7.30000 9.700

Propose a schematic diagram on the recrystallization of the crude compound AUBREY. Consider water as
the recrystallizing solvent. Indicate in each step the fate of the desired compound, impurities present and
the solvent used in recrystallization.

No part of this document may be reproduced by any means without the written permission of the Organic
Chemistry and Natural Products Division, Institute of Chemistry, UPLB.
EXERCISE 3

1. Substance A co-distill with water at 1 atm. Suppose that the vapor pressure of water at 95 OC is
748 mmHg, calculate the molar mass of substance A if 4.0 g of it co-distill with 34.0 g water.

2. Sebastian and his groupmates used 200 g of orange rinds as their sample for Exercise 3 of CHEM
40.1. The group stopped distillation when the volume of the distillate is 250 mL. Assuming that
distillation occurred at 97 OC and 1 atm, the vapor pressure exerted by water is 752.17 mmHg,
calculate the percent yield of the experiment. (density of water is 0.9934 g/mL).

3. Camphor (MM = 152 g/mol) has a boiling point of 204 °C at 1.15 atm. At 97.5°C, the vapor pressure
of water is 739 torr while that of camphor is 21 torr.
a. What is the mole ratio of camphor and water in the distillate?
b. Calculate the percent by mass of camphor in the distillate.
c. Is there any other component in the distillate?
d. If there is any, what is its Molar mass if it contains 6.4 grams per gram of water?

EXERCISE 4

1. Acetone extract of Moringa oleifera were analyzed using reversed-phase thin layer
chromatography. Using the data on the solubilities in water below, match the compounds to their
corresponding spot and calculate their respective Rf values using a ruler.
A 1.25 g/L
B 2.3 g/mL
C 490 mg/L
D 0.1 g/mL

No part of this document may be reproduced by any means without the written permission of the Organic
Chemistry and Natural Products Division, Institute of Chemistry, UPLB.
No part of this document may be reproduced by any means without the written permission of the
Organic Chemistry and Natural Products Division, Institute of Chemistry, UPLB.