P-Ester

Preparation of n-Butyl Cyclopropanecarboxylate

The chemistry you will use is outlined below:

A nice reference concerning this class of cyclization: https://dx.doi.org/10.1016/S0040-4020(01)01134-6. (On-campus or VPN/proxy access required)

You should be aware of several safety issues.

The chlorobutyronitrile is of the same chemical class as iodomethane, so keep it in the fume hood, try not to spill it, and use gloves throughout the experiment.
Powdered sodium hydroxide is very caustic; it is also extremely hygroscopic (it absorbs water from the atmosphere). Take care not to spill it, and transfer it to your reaction flask as quickly as possible.
The organic compounds used in this experiment are volatile and have disagreeable odors, so avoid keeping open containers of any of these outside the fume hood.
Addition of water to hydrolyze the nitrile causes a large amount of heat as the excess NaOH dissolves. Add water in 5-mL increments at first to avoid excessive heat buildup.

Several techniques are important to the succesful execution of this preparation:

Glassware needed for formation of the carboxylic acid

Grading:
50 points are possible for "Results." You will be graded on yield, purity and characterization you relate in Report I.

You should calculate the yield of pure carboxylic acid from chlorobutyronitrile.
You should calculate the yield of butylcyclopropanecarboxylate from cyclopropanecarboxylic acid.
You should then calculate the overall yield, which is the product of the two individual yields.

Your refractive index for the ester should match the literature value (1.4260 ± 0.0003 at 25°C); an acceptable temperature-corrected value will be within ±0.0005 of this.
You should take IR spectra of both the carboxylic acid and the ester; you need to identify any peaks in the functional group region, and establish that the fingerprint region matches that of a reference spectrum.
You should demonstrate with gas chromatography that the purity of the liquid ester is >99%. If the butanol peak is >1% the area of the ester peak, you must redistill. Be sure you have confirmed the retention time of each compound, and that the GC needle is not contaminated!
You will need to report the boiling range and pressure for each compound; this, like melting points of solids, is a characteristic physical property.