Separation of Benzoic Acid and Acetanilide

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Chem 3100 Thursday 9am-1:45pm
Olumba Obu
Unknown #: 146 Fall-11
Organic Chemistry Midterm Report
13 October 2011

Table of Contents
Separation of Benzoic Acid and Acetanilide 3
Extraction and Purification of Caffeine from Tea 4
Extraction of Trimyristin from Nutmeg 5
Conversion of t-butanol to t-butyl chloride 6
Appendix
7 Calculations 8 Literature and Experimental Values of Benzoic Acid and Acetanilide 9 Experimental Caffeine IR 10 Literature Caffeine IR 11 Experimental Trimyristin IR 12 Literature Trimyristin IR 13 Experimental Tert- Butyl Chloride IR 14 Literature Tert-Butyl Chloride IR and RI 15 References

Separation of Benzoic Acid and Acetanilide
Introduction:
The best way to separate an acidic or basic compound from a mixture is through an extraction. With the use of the separatory funnel, the insoluble liquid (organic layer) is separated from the soluble liquid (aqueous layer). The purpose of this lab is to separate a mixture of benzoic acid from acetanilide.
Procedure:
Obtain an unknown sample from instructor. The mixture is weighed out and place in a 125mL flask. 25 mL of methylene chloride was added to the mixture. Next the required KOH is added into the mixture, and refer to p. 117 from Wilcox &Wilcox.. The exception to this procedure is the use of a rotary evaporator instead of simple distillation.
Data:
Mass of Mixture | 3.9591 | Mass of Benzoic Acid | 1.204 g | Mass of Acetanilide | 1.372 g | % Recovery | 65.07 % | % Composition of Pure Benzoic Acid | 46.74% | % Composition of Pure Acetanilide | 53.26 % | Melting Point of Benzoic Acid | 122-125 Degrees Celsius | Melting Point of Acetanilide | 113-116 Degrees Celsius |

Results/Discussion:
The percent recovery of acetanilide and benzoic acid did not yield 100 percent. A possible cause of this was due to the loss of benzoic acid through filtration, so minuscule amounts of acetanilide residue were left



References: 2-Chloro-2-methylpropane. Chemblink.com. 2011. Web. 09 October 2011. Chemical Book. Chemicalbook.com. Web. 09 October 2011. SCHNITZLER, E. et al. Thermoanalytical study of purine derivatives compounds. Eclet. Quím. [online]. 2004, vol.29, n.1 [cited  2011-10-09], pp. 71-78 . The Vibrational Spectra and Assignments of t-Butyl Chloride and t-Butyl-d9 Chloride, and the Calculated Ionization-Equilibrium, Deuterium-Isotope Effect J. C. Evans and ,G. Y. -S. Lo Journal of the American Chemical Society 1966 88 (10), 2118-2122 Wilcox & Wilcox. Experimental Organic Chemistry: A Small-Scale Approach. New Jersey: Prentice Hall, 1995.

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