1.

Prepare a flow diagram for the isolation

(workup) of isopentyl acetate.
2.Add 10.9 mL (8.80 grams) of isopentyl alcohol
(2) (isoamyl alcohol) to a dry 50 mL round
bottom flask equipped with a stir bar and clamped
to a ring stand. Position an electric stirrer under
the flask so the stir bar gently rotates in the
isopentyl alcohol. Slowly add 12.5 mL (12.60
grams) of glacial acetic acid (1) to the isopentyl
alcohol. CAUTION: Acetic acid is a corrosive
acid!
3.Slowly add 2.5 mL of concentrated sulfuric acid
to the reaction mixture. WARNING: Sulfuric
acid must be added slowly to the reaction
mixture!
CAUTION: Sulfuric acid is very corrosive!
4.See Safety Sheet for disposal and neutralization
of acids. Do not place acids in the ORGANIC
WASTE CONTAINER!
5.Setup a reflux apparatus (See setup on front lab
bench) and reflux the reaction mixture for 35
minutes.
THE LAB INSTRUCTOR MUST CHECK
YOUR APPARATUS BEFORE YOU BEGIN
REFLUXING!
6.After refluxing remove the heating mantle and
allow the apparatus to cool for 5 minutes. Place
an ice bath under the 50 mL reaction flask and
cool for an additional 5 minutes. Do not remove
the reflux condenser or turn off the water
running through the condenser during the
cooling process!
Workup
1.Pour the cooled reaction mixture into a 125 mL
separatory funnel. Pour 25 mL of cold water into
the 50 mL flask, swirl it to rinse the flask, and
then add the aqueous solution to the separatory
funnel.
2.Stopper the separatory funnel and rock the
funnel as described in the extraction experiment.
Be sure and vent the funnel two or three times
during the extraction.

3.Allow the two liquid phases to separate, then

drain off and discard the aqueous layer. WHICH
LAYER IS THE AQUEOUS LAYER? Note: If
the two layers do not separate, add 25 mL of
saturated sodium chloride solution.
4.Extract the organic layer (isopentyl acetate)
with 25 mL of 10% sodium carbonate solution.
CAUTION: A LARGE VOLUME OF
CARBON DIOXIDE IS RELEASED IN THIS
PROCESS.
5.Drain off the aqueous layer and check it for
acidity using litmus paper. Re extract the organic
layer with 10% sodium carbonate solution if the
solution is still acidic.
6.GENTLY extract the organic layer (isopentyl
acetate) with 10 mL of saturated sodium chloride
solution. Drain off the aqueous layer and transfer
the organic layer (isopentyl acetate) to a 150 mL
beaker.
7.Add a small amount of anhydrous magnesium
sulfate to the beaker (enough to cover the bottom
of the beaker), swirl and then let the solution
stand for 10 minutes.
8.Using a fluted filter paper gravity filter the
isopentyl acetate into a 50 mL round bottom flask.
Seal the round bottom flask with a Teflon stopper
and wrap the teflon stopper with parafilm.
The distillation step will be completed in the next
lab period.
Isolation and Purification
1.Set up a simple distillation apparatus (see
distillation apparatus on front bench) and distill
the isopentyl acetate (3). CHECK WITH THE
INSTRUCTOR BEFORE STARTING YOUR
DISTILLATION.Check the position of your
thermometer. (Why is the position of the
thermometer important?
2.Collect the fraction that distills between 130 C
and 143 C in a preweighed 25 mL round bottom
flask. Record the boiling point and mass of your
collected fraction. Transfer the purified isopentyl
acetate to a labeled vial.