Purpose: The purpose of this experiment is synthesizing the organic compound by using separation methods.

This separation method is called simple distillation. The simple distillation is a separation process that synthesized 4-methycyclohexene from dehydration of methylcyclohexanol. In this lab, 4methylcyclohexanol reacts with phosphoric and sulfuric acid to produce 4-methylcyclohexene. This alkene mixture experiment, purified by simple distillation to determines the product that produced.

Reagent required: 7.5 mL of 4-methylcyclohexanol (mw =114.2, Boiling point =171-173c) 2.0 mL of 85%phosphoric acid, h3po4 30 drops (0.04mL) of concentrated sulfuric acid,h2so4 Saturated sodium chloride,NaCl Granular anhydrous sodium sulfate,Na2SO4 Bromine test reagent Pottassium permanganate test reagent

Apparatus required: 50 mL round bottom flask 25mL round bottom flask Erlenmeyer flask Glass stirring rod Pastuer pipets Boiling stones Distillation apparatus Ice bath water Heating mantle Weighning balance

Procedure : The apparatus for simple distillation was set up before proceed the experiment. The ice bath was placed around the receiver flask in order to lessen the loss of product by evaporation. 50mL empty round bottom flask was weighed and by using graduated pipette, 7.5 mL of 4-methylcyclohexanol was pipets into a round bottom flask. The flask was reweighed. 2.0mL of 85% phosphoric acid and 30 drops of concentrated sulfuric acid along with 1 and 2 boiling chip was added in to the distillation flask and mixed thoroughly. The flask was heated with a heating mantle and distilled slowly while maintaining the

distillation temperature below 100c. the distillation process was continued until about 0.5-0.6 mL of residue remains in the distillation flask or the mixture begin to smoke or bump. Next, the distillate mixture was mixed with NaCl solution and transferred into a test tube. The test tube was closed and shake gently to allowed layer to separate. Drawn off the bottom aqueous layer with pastuer pipet and discard. Transfer the crude 4-methylcyclohexene to an Erlenmeyer flask. A small amount of anhydrous sodium sulfate and a stopper was placed on the flask. The liquid was dried for about 15 minutes with occasional swirled. During the drying interval, the distillation apparatus was cleaned , dried with acetone. 25.0 Ml round bottom flask that has been weighed while capped. The dried cyclohexene with a Pasteur filter pipet into the distillation apparatus. 1 or 2 boiling chips was added and proceed with distillation process. Reweighed flask and calculated percent yield of 4-methylcyclohexene.