CHEM 2203 Fall 2014

Modifications for Expt 12: Reductive Catalytic Hydrogenation of an Alkene:

Decane
Please incorporate the following modifications to the lab textbook procedure:
Reagents and Equipment
Substitute 1-decene for 1-octene as the substrate. Look up the physical properties of 1decene and decane, include them in your lab notebook, and use them in your calculations.
The procedure calls for preparation of a solution of the substrate, 1-decene, in absolute
ethanol. This solution will be pre-made using the same amounts described in the
textbook for 1-octene: 120 L of 1-decene dissolved in 250 L of absolute ethanol.
In terms of concentration, this solution is 32.4 v/v% of 1-decene in absolute ethanol.
Use the same amount in mmoles of 1-decene = 0.76 mmol.
The volume of the pre-made solution of 1-decene in absolute ethanol that will afford
0.76 mmol of 1-decene is 440 L (rounded to two sig figs for practical reasons).
So, add 440 L of the pre-made 1-decene solution in ethanol, via a clean syringe, to
your reaction mixture.
Where did this value come from? You are responsible for knowing how to perform the
necessary calculations!
Isolation of Product
Perform the pentane extractions carefully. It is preferable to leave some of the organic layer
behind each time, rather than try to withdraw all of it, and thus increase the chances of taking
some of the aqueous layer as well. If too much water is transferred, a lot of sodium sulfate will
be required in the drying step. As three extractions are utilized, any overall loss of product
should be negligible.
Instead of a stopper, the 25-mL Erlenmeyer flask containing the organic extracts may be
covered loosely with centrifuge tube cap or a small watch glass.
The use of sodium sulfate as a drying agent should be a familiar procedure by now. There is
no need to weigh it. Proceed as in previous experiments.
The purification procedure (see below) will not be performed, so the crude product should be
concentrated fully in this step. Transfer the dried solution by filter pipet to a tared screw-cap
test tube containing a boiling stone, and place in the heater block. What is the expected form
of the product solid or liquid?
Purification and Characterization
The crude product will not be purified by column chromatography.
Obtain the weight of the crude product only (no boiling point or refractive index).
A representative IR spectrum for the entire section may be obtained as directed by your TA.