Organic Chemistry Lab 315

Fall, 2016
Lab does not meet on Tues., Oct. 11.
(Monday classes meet).
 DUE DATES
• Today
– At beginning of lab – Identification of an Unknown
Report
– Problem #1, Part II, Spectroscopy Problem Set
– At end of lab -- copy of laboratory notebook pages
for today's experiment (do not turn in your pre-lab
notes or in-class notes)

• Next Week (when we meet)

– Part II, #2 Spectroscopy Problem Set

– Extraction of Caffeine Report

 Report Notes – Last Week
• Pay attention to significant figures in
calculations. Review them if necessary.
• You cannot add a digit to an
experimentally determined mass.
– Example: mass = 1.254 ± .001 and for some reason you add “0”
and use 1.2540. You would not add a “2” for example – why
would you add any digit to the data?
• Properly labeled vial example in Pavia. It
must include the melting point range – you
always report ranges (and it is an
indication of purity).
 In Lab Today
• Learn the new technique of extraction.

• Drying organic solvents (See p. 697 in

Pavia).
Experiment Notes
Beaker containing
dissolved caffeine
and insoluble binder

Funnel with glass

wool as filter

Separatory funnel
supported on iron
ring on ring stand

Stopcock closed

Beaker underneath
“just in case”
Experiment Notes
Beaker containing
dissolved caffeine Separatory funnel
and insoluble binder with stopper

Funnel with glass Aqueous layer on

wool as filter top

Separatory funnel Methylene

supported on iron chloride layer on
ring on ring stand bottom (contains
caffeine)
Stopcock closed

Drain off CH2Cl2

bottom layer into
Beaker underneath beaker
“just in case”
Total 3 extractions
(8 ml x 3)
 Experiment Notes
Extractions in a Separatory funnel
•Add liquids using a glass funnel in order to not
Remove stopper before
contaminate the neck of the sep. funnel.
separating phases.

•After replacing the stopper, turn the sep. funnel

upside down to vent. Repeat if audible/visible gas
escapes.

•Shake/swirl gently, but thoroughly, to mix the

immiscible liquid phases. An emulsion may form in
this experiment. Stopcock should be closed!

•Caffeine is in the bottom CH2Cl2 layer. Drain bottom

layer through stopcock into 100 ml beaker. [This is
one extraction.]

•Add additional CH2Cl2 (using glass funnel) from top.

•Extract with CH2Cl2 three times total, combining all

extracts in beaker.
 Experiment Notes
Drying Organic Solvents

There will be water dissolved in the CH2Cl2 extracts that

needs to be removed.
Organic solvents are “dried” by using an anhydrous salt that
can absorb the water and become hydrated.
See Section 12.9 in Pavia for common drying agents and
equations for anhydrous salt → hydrated salt
MgSO4 + H2O → MgSO4∙10H2O
When you are ready to dry your solution, bring it to the
instructor’s bench.
After drying, decant the solution into a pre-weighed beaker.
 Experiment Notes
• Make sure the balance is displaying ±.001g
• Evaporate solvent using a hot plate UNDER THE HOOD.
• Do not recrystallize caffeine.
• Weigh the beaker and mostly dry caffeine.
• Place your caffeine in a properly labeled vial. See Pavia
for an example of a correctly labeled vial.
• Caffeine tablet contains 200 mg of caffeine. The
remainder is “inert ingredients”.
• Calculate the % isolation based on the mg caffeine in the
2 tablets.
 Report for Next Week
• Report Form in Manual
• Separation Scheme (flow chart of procedure for
separating a pure product from reaction by-
products or mixture impurities).
– See explanation and example in Manual/class web
page.
• There is no other written report required (major
grading will be for the Separation Scheme – be
sure you understand it).
 Report for Next Week
• Some additives in Vivarin:
– polyethylene glycol and polysorbate 80
(water-soluble)
– titanium dioxide and silicon dioxide (water-
insoluble)
– D&C yellow #10 and yellow #6 aluminum lake
dyes (water-insoluble)
– carnauba wax (water-insoluble)
– dextrose (water-soluble)
 Report for Next Week
• These additives should be included in your
Separation Scheme for isolating caffeine from
Vivarin tablets. You do not need to find the
structures for these compounds.

• You can ignore the effect of Na2CO3 on the water-

solubility of any of these additives, although
Na2CO3 should be included in the scheme.
(Na2CO3 was added to the Vivarin-water solution.)
 Report for Next Week
• Your Separation Scheme should resemble
the one done for isolation of caffeine from
tea leaves, shown in class. (It would be
helpful if you printed the linked page and
brought it to class.)
• Tea leaves separation
Right-click on the hyperlink above, and then
choose “open hyperlink”’
 Weekly Clean-up
•