To develop organic laboratory techniques, to synthesize 4-methylcyclohexene, and to gain experience using Fourier Transform Infrared (FTIR) Spectroscopy to characterize the product of a reaction.
As we have previously noted, alcohols are not good leaving groups. However, the addition of an acid to an alcohol can convert a bad leaving group, hydroxide, to an effective leaving group, water. In the absence of a nucleophile, a protonated alcohol can undergo an elimination reaction. The synthesis of 4-methylcyclohexene can be accomplished in this way.
H2SO4, H3PO4 OH
Although the synthesis of 4-methylcyclohexene is ...view middle of the document...
Saunders College Publishing, 1999.
mL conical vial. Continue collecting the distillate until the reaction mixture stops boiling. Approximately 0.5 mL will remain in the reaction vial. Transfer all of the distillate to the 3mL conical vial. Using a Pasteur pipet with a bent tip, rinse the material clinging to the walls of the condenser into the well of the Hickman head with 1 mL of a saturated, aqueous sodium chloride solution. Transfer the rinse from the well of the Hickman head to the 3-mL vial. Isolation of 4-methylcyclohexene Allow the distillate to separate into layers. Remove the aqueous layer, and after confirming its identity, discard it. Transfer the organic layer to a small, clean, dry test tube. Add 3–4 microspatulas of anhydrous sodium sulfate to the test tube, and allow the drying agent 15 minutes to dry the product. Carefully transfer the dry 4-methylcyclohexene to a tared, clean, dry vial. Determine the mass of the 4-methylcyclohexene collected. Analysis of the 4-methylcyclohexene IR Spectrum Obtain an IR spectrum of your product using the Attenuated Total Reflectance FTIR Spectrometer. After collecting your spectrum, wash the Ge crystal with acetone, dry the crystal with a piece of lens paper, and return the crystal to the spectrometer. Make certain to...