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Dehydration of 2-methylcyclohexanol

concentrated mineral acids such as sulfuric acid (H2SO4) and phosphoric acid (H3PO4).Dehydration Reactions Alcohol dehydration is an acid catalyzed reaction. which can be performed by strong. .

removes a proton from the carbon adjacent to the positively charged carbon. forming an alkene and regenerating the acid catalyst H3PO4. 2nd step .Background Alcohol dehydration proceeds by an elimination mechanism called E1. Saytzev’s rule: The more substituted alkene is the more stable product (major product).Protonation changes the very poor CH3 departs.Water major product 3rd step . OH CH3 H-O-PO3H2 H + O-H CH3 rate determining step H + H CH3 H carbocation rearrangement CH3 + oxonium ion secondary carbocation O-PO3H2 O-PO3H2 tertiary carbocation O-PO3H2 CH3 1st leaving group (-OH) into a good leaving group (H2O). leaving behind a carbocation. step . This step is the rate determining minor product step (rds).The base H2PO4. .

Dehydration of 2-methylcyclohexanol bp 165° C carbocation rearrangement minor products major product bp 110° C .

No sulfuric acid is used. . Only the qualitative test with Br2 is performed. GC is performed on the product mixture. Use 6 mL of 2-methylcyclohexanol and 5 mL of phosphoric acid.Experimental Procedure Changes from the Manual procedures: Use heating mantel instead of sand bath. Don't forget boiling chips. Test acetone as a blank. and the product. and the starting material. No refractive index will be measured.

. Do not distill to dryness.Distillation Set Up Set thermometer bulb even with the joint of the distilling head (NOTE: this drawing shows it to be too low!) Heating mantel sitting on lab jack Do not allow temperature to rise above 100 ºC.

and let it sit for 10 min. . Organic layer containing all products (KEEP!!!!) Water layer (Use pipet to discard into waste bottle) Add 0. you need to add CaCl2. shake it up.5-1.0 g CaCl2 to the centrifuge tube.Transfer distillate to a clean centrifuge tube. dissolve the pot residue in water and transfer to the same waste bottle as the aqueous layer. Do not transfer any CaCl2. shake. then allow layers to separate. Weigh the product. calculate % yield and then perform the unsaturation test. allow to stand for 10 min. Transfer the dried product to a preweighed sample vial. (Tube must be stoppered).) While the product stands. (NOTE: Even if you cannot see any water separated from the distillate.

. Observe any color change within five minutes. Add 20 drops of acetone into each test tube and shake. and one for products. one for the blank. Add 2 drops of Br2 test reagent to each tube and shake. Place 2 drops starting material and the product in each test tube.Bromine test: To distinguish between saturated and unsaturated compounds. employ the observation of color changes. Label three small test tubes. one for the starting material (methylcyclohexanol).

Methylcyclohexenes are highly fammable. Report the ratio of the products (equal to the ratio of peak areas). Area = h X w Cautions: Phosphoric acid is highly corrosive. Br2 is toxic and an oxidizer. then inject 1 µL into GC. Measure the peak height (h) and width (w) (at half the peak height). Do not use the calculated areas on your chromatogram.GC analysis: Dissolve 2-3 drops of product in 1 mL of acetone. Identify peaks by comparing retention times with those of the pure alkenes (These will be posted). Grading is 50% for the written report and 50% for results and observations. .