H-Ester

Preparation of Methyl Cyclohexanecarboxylate

The chemistry you will use is outlined below:

You should be aware of several safety issues.

The chlorocyclohexane 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.
The Grignard reagent is a strong base and very caustic; your gloves again serve as protection for your hands. The reagent is also quite air-sensitive, and ether is quite flammable. Be sure to get help from a TA when doing the transfer from the reaction flask back into the addition funnel!
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.

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 chlorocyclohexane.
You should calculate the yield of methylcyclohexanecarboxylate from cyclohexanecarboxylic 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 (1.4408 ± 0.0002 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%.
You will need to report the boiling range and pressure for each compound; this, like melting points of solids, is a characteristic physical property.