Extraction and Isolation of Caffeine from Tea Leaves Organic Chemistry Lab (Online) Manual

Activity Extraction and Isolation Date

No. of Caffeine from Tea Leaves
Instructor’s Group No. Name Score
Signature
Date Rating

R ESULT:

1. Fill-up the table. (1 pt each)

Description of Tea Leaves

color texture

2. Description caffeine crystals (1 pt each)

Description

caffeine color shape

crystals

crude

recrystallized

Q UESTIONS:

1. What group of compounds does caffeine belong to? (1 pt)

2. Draw a separatory funnel showing the two distinct liquid layers that appeared during the
extraction process. Label the layers as aqueous or organic. (3 pts)

What physical property would explain why one layer is on top of the other layer? (2 pts)

Dept. of Chem. MSU-IIT AY:2020-2021Page 1

3. If too much drying agent is added to the extract, what is its overall effect on the final product?
(2pts)

5. Consider the structure of caffeine and provide an explanation for the difference in the in the
average mass of caffeine collected. When explaining the difference consider, how HCl might
or Na2CO3 interact with caffeine. Consider how charged molecules (ions) interact with water as
compared to neutral molecules; in other words, which would be more soluble in water, a
neutral caffeine molecule or a charged caffeine molecule. Which would be more soluble in an
organic solvent, a charged molecule or a neutral molecule?

6. Assuming that you are not told which layer is methylene chloride and which is the aqueous
layer, how will you identify the two later experimentally? (2 pts)

6. Caffeine is soluble in methanol, as well as methylene chloride. Why couldn’t you use methanol
to extract the caffeine from the aqueous portion? (2pts)

7. Dichloromethane is generally nasty stuff. What could be used to replace halogenated

solvents in this extraction procedure? Hint: Where does decaffeinated coffee come from?
Give reference. (3pts).

8. Make a schematic diagram for this experiment. (5 pts)

References

Murray, D.S.; Hansen, P.J., J. Chem. Educ., 1995 (72) 851. Hampp, A., J. Chem. Educ., 1996 (73)
1172.

Adapted from Introduction to Organic Laboratory Techniques: A Microscale Approach , 3rd edition.
Pavia, Donald L., Gary M. Lampman, George S. Kriz, and Randall G. Engel (1999).