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CHMY 222 OrgChemLab, section 3 T/Th 10-12pm TA:

Preparation of 4-Methylcyclohexene Introduction: In this experiment a very simple elimination reaction is induced to produce an alkene. The hydroxyl group of 4-Methylcyclohexnol is eliminated by protonation of a strong acid, H2SO4 and H3PO4. The 4methylcyclohexene produced is isolated and dried using distillation. The un-saturation of the alkene is checked by bromine solution color test. IR is then used to test the sample. Chemical information: Reagent/Solvent 4Methylecyclohexanol, C7H14O Amount used 1.5 mL MW Moles used Info.

114.19 83.90 mol D 0.914 g/mL g/mol Bp 171-173 C Avoid contact with skin/eye

Phosphoric H3PO4

acid,0.4 mL

98.00 129.97 molD 1.885 g/mL g/mol Bp 158 C Corrosive

Sulfuric acid, H2SO46 drops Conc.

98.086 177.69 molD 1.84 g/mL g/mol Bp 337 C Corrosive, very reactive and


Sodium1.0 mL

58.443 26.99 mol D 2.165 g/mL g/mol 142.04 g/mol 96.172 g/mol Bp 1413 C D 2.664 g/mL Bp 1429 C D 0.799 g/mL Bp 101 C Flammable, Inhalation vapor cause avoid contact of might irritation, skin/eye

chloride, NaCl Anhydrous sodium sulfate, Na2SO4 4-Methylcyclohexene,


Flow Diagram: Weight 5mL conical flask add 4-methylcyclohexanol reweight add phosphoric acid and 6 drops of sulfuric acid and a stirring bar assemble hickman distillation apparatus heat to +150 C transfer the distillate from hickmans head to a conical flask rinse head with saturated sodium chloride solution allow layers to separate then remove the bottom aqueous layer and dry with anhydrous sodium sulfate perform a functional group test and an infrared spectroscopy. Procedure, Observations and Results: 1.5 mL of 4-methylcyclohexanol was placed into a 5 mL preweighed conical vial. The vial was then reweighed to measure the amount of alcohol present by weight. 0.40 mL of 85% phosphoric acid and about 6-7 drops of concentrated sulfuric acid were added to the alcohol in the vial. A magnetic spin vane was placed in the vial and was

allowed to spin the liquids into a mixture. The vial was then attached to a distillation apparatus using a Hickman head and a water-cooled condenser. The mixture was then heated on a hotplate using an aluminum block. The vial was allowed to heat to about 170 C to avoid the alcohol from co-distilling with the water and product. The distillate was removed as soon as there was enough of it to transfer to a clean and capped vial. The distillation was allowed to continue until there was no more boiling in the vial. The inside wall of the Hickman head was then rinsed with a 1 mL portion of saturated sodium chloride solution. The rinsed liquid was then added to the collection vial. The bottom aqueous layer was removed and discarded using a pipet. The remaining organic layer was dried over granular anhydrous sodium sulfate for about 5 minutes. The organic layer was then transferred to a pre-weighed and capped vial that was then weighed again and the percentage yield was determined. IR and GC were used to test the sample. The remainder of the sample was tested against a bromine solution and potassium permanganate. Similar tests were done to the starting alcohol for comparison. The end product was a clear liquid. The collected sample weighed 0.278g. Theoretical yield: Weight of alcohol = 1.182g. || 1.182g / 114.2g per mol x 96.2g per mol = 1.000 g Percent yield: 0.278g/1.000g x 100 = 27.8% The functional group went as follow: Br2 4-Methylcyclohexanol 4-Methylcyclohexene Yellow Clear KMnO4 Clear some ppt Brown ppt

Mechanism of product synthesis:

Conclusion: The IR spectrum shows the presence of an Alkane stretch group, a clear and sharp Alkene group and a tiny peak for OH. The minute peak for OH indicated the reaction went rather well and almost all the alcohol converted to the final product. The medium absorption alkene group peak occurring at around 1450 cm-1 indicates an aromatic alkene, which means the procedure went well and the final product is available. The low percent yield can be attributed to several factors. Using phosphoric acid is not as good as using sulfuric acid, but sulfuric acid chars the sample. So not all the alcohol converted into the final product. The part of the alcohol that actually converted to the 4methylcyclohexene was still reduced more in the distillation process. The amount of condensing liquid droplets on the wall of the Hickman head were difficult to remove by a small portion of saturated sodium chloride solution. Separating the two liquid phases was particularly difficult to perform accurately. The Saturated sodium chloride was used to rinse the Hickman head after the first distillation to wash the phosphoric acid that distills with the product and to partially remove the water from the organic

layer before drying it with granular anhydrous sodium sulfate after separation. The Bromine solution test was easier to spot and clearly indicated the presence of double bonds. Questions/Exercises: 1around the methyl group. the last product (#3)

is the most dominant one because of the double bond substitution

2- Because of the position of the OH group, the double bond will move around through the ring until it reaches the methyl group.

3- The boiling point of the alcohol is higher than the alkene as seen on the chemical information table. Because of the strong intermolecular forces in the alcohol. 4- Therere 4 stereoisomers for the 4-methylcyclohexanol, Cis and Trans. They differ in the position of the substituent groups. The cis isomer has both substituents on the same side, while trans isomer has subsituents on opposite sides.