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Halogenation of a Substituted Benzene Ring By: John Doe CHEM 210(1 or 2, as appropriate)L – Lab Day (M, T, W, R, or F) Date(s) Lab Performed (don’t forget any days you collected additional data.)

Samplle Reportt ((Be sure tto Doublle Space)) Samp e Repor Be sure o Doub e Space Abstract The purpose of this experiment was to halogenate a substituted benzene ring. Acetanilide, a substituted benzene ring, was reacted with bromine in acetic acid and hydrobromic acid at room temperature to prepare para-bromoacetanilide. A product was obtained in a yield of 0.12 g (86%) and with a melting point of 150-157 °C. An infrared spectrum of the product showed bands at 3300, 1700, 1600 and 1500 wavenumbers. A 1H NMR of the product showed signals at 2.04, 7.45, 7.56, and 10.02 ppm. The halogenation of a substituted benzene ring (acetanilide) with bromine was successful since parabromoacetanilide was obtained as shown by melting point, infrared, and 1H NMR analysis. Introduction Get background from McMurry (and/or other referenced material) regarding the reaction that was carried out. For example, who discovered it, significant intermediates, and/or why it is important.1(show references after each new statement of fact) Reaction Give the overall chemical reaction with structures and names of all reactants and products. Make sure you include the reaction conditions and reaction mechanism. Give the mechanism specific to this reaction using structures and arrows. You must use the software ChemDraw (or other chemical drawing software). Be sure it is neat and has good resolution. Experimental details2 Acetanilide (0.090 g, 0.67 mmol), glacial acetic acid (0.5 mL), and a spin vane were placed in a 5 mL conical vial. The vial was fitted with an air condenser and placed in a 23 – 27 ºC water bath. The mixture was stirred to dissolve the acetanilide. A mixture of 2.5 M bromine/7.7 M hydrobromic acid (1.0 mL, 2.5 mmol Br2) was added to the vial...

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