Alkylation of m-Xylene - Alkylation of m-Xylene Last...

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Alkylation of m -Xylene Last update: 22 August 2005 Dr. Glenn Nomura Reference : 1. Williamson, Macroscale and Microscale Organic Experiments , 4 th edition, Houghton Mifflin: New York, 2003, Experiment 29.5, (2X) microscale alkylation of m -xylene, p. 384 2. Click, http://ocw.mit.edu/OcwWeb/Chemistry/5-301January--IAP-2004/StudyMaterials/index.htm to view Reaction Work-Up I’ ; although the MIT video illustrates the extraction technique in macroscale, the theory and practice of extraction is scalable to the test tube scale of this experiment. Equation: CH 3 CH 3 CH 3 H 3 C C(CH 3 ) 3 H 3 CC l CH 3 CH 3 FeCl 3 m-xylene MW 106.17 d 0.868 bp 139 o C 2-chloro-2-methylpropane or t-butyl chloride MW 92.57 d 0.851 bp 51 o C Materials: 1. m-xylene, 1.2 mL (0.00981 mol) 2. t-butyl chloride, 1.0 mL (0.00919 mol) 3. iron (III) chloride, 60 mg Procedure: Prepare one calibrated Pasteur pipet to contain 1.2 mL and another to contain 1.0 mL. As an alternative, the instructor may set up two burets for dispensing m-xylene and t-butyl chloride. As an alternative to the Williamson order of steps, add approximately 60 mg of FeCl 3 catalyst ( Note A ) to a clean dry test tube and followed by 1.2 mL of m-xylene. Add the 1.0 mL of t-butyl chloride last to this mixture and be prepared to install the septum immediately and immerse the test tube in ice water. A septum fitted with a polyethylene tube leading to a second test tube containing a wad of cotton wetted with water serves as an HCl trap. Cool the reaction test tube in an ice bath slush. The reaction will immediately evolve HCl gas bubbles even at 0°C The reaction will continue to bubble vigorously for about 15 - 30 minutes. The rate of bubbling will indicate how far along the reaction has proceeded. When the bubbling has subsided, take the septum off and add 2 mL of water to the reaction mixture, mix the contents by placing a pipet at the bottom of the reaction mixture and
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Alkylation of m-Xylene - Alkylation of m-Xylene Last...

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