Preparation of Methyl Cyclohexanecarboxylate

The chemistry you will use is outlined below:

A useful background paper on the mechanism of Grignard reagent formation--particularly the origin of radical coupling products--is here..

• 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.

Grading:

• 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 ±.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.