CHM$2201$ Summer$2011$ Department$of$C hemistry$Organic$Chemistry Lab I Villanova University Page 1 of 3 Dehydration of 2-Methylcyclohexanol Period 6 – June 20, 2011 Bell, Clark & Taber, pgs. 205 – 209 (Expt 20B) CH3OHCH3CH3MW = 114.19Amt. = ~ 6 mLWt. = ______ gd = 0.93 g/mL+MW = 96.17d = 0.80 g/mLMW = 96.17d = 0.81 g/mLH3PO4Heat+CH23-Methylcyclohexene1-Methylcyclohexene123 123Methylenecyclohexane(A p ossible side product) UCarry out this reaction in your hood 1. Add to a 25 mL round-bottom flask: a. 6 mL of 2-methylcyclohexanol (Avoid contact with skin; do not breath vapors) b. 5 mL of 85% phosphoric acid (CAUTION!!: corrosive liquid) c. UTWO or THREEU boiling stones 2. Attach the flask to a simple distillation apparatus as illustrated on the next page. Use a centrifuge tube as the collection receiver. 3. Heat the flask slowly to boiling and distill the formed alkenes while keeping the distillation head temperature below ~96°C by regulating the rate of heating. 4. Collect a total of 4 to 6 mL of distillate in a centrifuge tube receiver. (A small narrow tube is best for your distillation receiver since it will be easier to separate and isolate the product). The distillate that you collect in your receiver may consist of two layers: a. Upper layer: the majority of the distillate is contained in this layer and it consists of the desired mixture of cyclohexenes. b. Lower layer: if this layer is present, it should be present in a smaller amount and consists of water which codistilled with the cyclohexene products. 5. Using a disposable pipet, carefully separate the desired upper layer of the distillate from the lower water layer and transfer it to a clean dry Upre-weighedU test tube (HINT: Place the test tube in a beaker to hold it for weighing). Try not to contaminate the cyclohexenes with water from the lower layer if it is present. 6. After the cyclohexenes have been transferred to the pre-weighed test tube, reweigh the test tube (use the beaker method) and its contents to obtain the weight of the product so that you can calculate your approximate % yield. 7. After weighing the test tube and its contents, dry the product by adding some solid anhydrous sodium sulfate to the liquid product in the test tube; initially, add enough sodium sulfate to amount to about ¼ of the total volume of liquid. Stir the contents with a spatula to mix the drying agent with the liquid. If you observe only large chunks of drying agent, add another small portion of sodium sulfate, stir it and observe if the added sodium sulfate is loose and finely divided and not chunky after stirring the mixture; if it is finely divided, you have added enough drying agent. Allow the mixture to sit for ~5 – 10 minutes with intermittent stirring to ensure that the sodium sulfate contacts all of the liquid to maximize thorough drying of the liquid.CHM$2201$ Fall$2010$ Department$of$C hemistry$Organic$Chemistry Lab I Villanova University Page 2 of 3 TMBare (9/12/2010)/ JWB 5/2011 8. Using a clean disposable pipette, transfer 10 drops of the clear dried product (avoid allowing particles of sodium sulfate drying agent to get into the pipette) to a small vial with a screw cap and use this small sample for subsequent GC and IR analysis. 9. Analyze the composition of the product by GC analysis. The TAs will inject the sample for you. Identify the two main components of the reaction product by comparison of retention times (previously determined for each instrument) with authentic samples of 1-methycyclohexene (bp 110°C) and 3-methylcyclohexene (bp 104°C). a. Which cyclohexene isomer was formed in greatest amount? What is the approximate % composition of the two isomers? b. Why was the predominant isomer formed in the greatest amount? c. Based on the boiling points of the two major cyclohexene products, which would you predict to have the shortest GC retention time? Why? Does your prediction correlate with your experimental observations? d. Did you observe any additional peaks other than the two expected main products? e. Another product that could be formed in small amounts from this dehydration reaction is methylenecyclohexane (bp 102 - 103°C). Did you observe a small gc peak that might correspond to methylenecyclohexane based on its boiling point? f. Theoretically, how could methylenecyclohexane be formed in this reaction? Show a mechanism for its formation. 10. Take an infrared (IR) spectrum of your dried dehydration product (Urequest a TA to help take the IRU); compare the IRs of starting material (2-methylcyclohexanol, provided to you as a handout) and your product mixture and explain key functional group absorption band changes which indicate that the alcohol dehydration occurred to provide the desired alkene products. 11. Compare the IR of your product with the IRs of pure 1-methylcyclohexene and 3-methylcyclohexene (both spectra provided to you as handouts). a. Can you observe absorption bands in the IR of your product mixture that are unique to either of the pure cyclohexene isomers? b. If you did not have a GC analysis to determine the relative amounts of the cyclohexene isomers formed, could you, by closely examining the IRs of your product and the two individual pure cyclohexene isomers, predict which isomer is present in the greatest amount? How could you do this? NOTE: The answers to all highlighted questions should be answered in the conclusion section of your write-up.CHM$2201$ Fall$2010$ Department$of$C hemistry$Organic$Chemistry Lab I Villanova University Page 3 of 3 TMBare (9/12/2010)/ JWB 5/2011 ThermometerSimpleDistillationHeadCondenserWater In (water flows uphill )Water OutKeck ClipKeck ClipBoiling Flask(Distillation Pot)BoilingStonesHeat S ourceVacuumTakeof fAdapter3 ProngClampSimple Distillation ApparatusNote position ofthermometer