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The Synthesis: Slowly heat the reaction mixture up to reflux (keep hot plate tem

ID: 956258 • Letter: T

Question

The Synthesis: Slowly heat the reaction mixture up to reflux (keep hot plate temperature 160 180 "C). Intermittently check the temperature of hot plate by inserting a thermometer in opening on aluminum block. Make sune to stir the reaction mixture. Heat the reaction at reflux for 30 minutes. To ensure a high temperature in the vial, it may be helpful to wrap aluminum foil around the flask, however do not wrap the Hickman head or condenser as that would prevent condensation and collection of the distillate. As the product, 4- methylcyclohexene, is formed it will distill and collect in the Hickman head. If you have a side-port in Hickman head then remove the product as it is forms. Place the collected product in a clean conical vial. Make sure to cap it to prevent product evaporation. If you do not have a Hickman head with side port then wait until the reaction is complete to remove the distillate. The reaction will be done when the reaction mixture stops boiling. The Purification/Work-u Remove the product from the Hickman head using a pipet. Then rinse the head with 3.0 mL of saturated sodium chloride. Add the sodium chloride rinse to the conical vial containing the 4-methylcyclohexene product. Shake, and then allow the layers to separate. Remove the aqueous layer (set aside but do not discard yet). Then transfer the organic layer (containing your product) to a clean and dry conical vial and dry it with anhydrous sodium sulfate. Next, either carefully decant the liquid product, or filter it through a cotton-plugged glass Pasteur pipet, into a pre-weighed conical vial. Determine the mass of the product and calculate the percent yield. The Characterization/Identification: The product will be characterizcd by Br test. Br Test: Place 4-5 drops of the starting material 4-methylcyclohexanol (colorless) in one test tube. Place 4-5 drops of the isolated product 4-methylcyclohexene (colorless) in another test tube. Clearly label or mark the test tubes. To each test tube add 2-3 drops of a bromine solution in CH Cl or CCL4). Record the physical observations of the solutions in cach test tube. Prelab Report: Make sure to write a good prelab report in your lab notebook before coming to lab. Apart from the usual components of the prelab report include the following: 4-Methylcyclohexene synthesis reaction. 4-Methylcyclohexanol, 4-methylcyclohexene, H:PO, HSO4, CaCl2, NaC, Na SOs, CH Cl2 and acetone in the table of reagents. * Calculation of limiting reagent and theoretical yield based on the amounts given in this handout A neat hand-drawn diagram of the apparatus given in this handout. Postlab Report: Tis is a synthesis experiment and you'll have more data and observation in this experiment, therefore, a well written report, in your lab notebook, is expected. Apart from the usual components of the postlab report, write a complete arrow pushing mechanism for the synthesis of 4 methylcyclohexene and describe each step of the mechanism in your own words. Include the reaction of Bra test and clearly expla : Clearly ex g chemicals in this Alkene Synthesis experiment: H2SO4, 2) H3PO 3) CaCl 4) NaCl, 5) Na2SO 6) B2 in

Explanation / Answer

NaCl is used in order to separate the organic and inorganic layers.

Br2 in CH2Cl2 is used in order to characterizate the product. This reaction let bromation happen in the alkene molecule.

H2SO4 is used in acid dehydration with heat in order to produce the alkene(150°C).

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