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 …show more content…

Conversion of t-butanol to t-butyl chloride
Introduction:
Tertiary alcohols can be converted to alkyl chlorides by the addition of concentrated hydrochloric acid to the alcohol via SN1 reaction (Wilcox & Wilcox, 310). The purpose of this experiment is to convert t-butyl alcohol to t-butyl chloride via an SN1 reaction.
Procedure:
Obtain all chemicals before starting, and refer to p. 315-316 from Wilcox &Wilcox. The exception to this procedure is to take the IR and RI of t-butyl chloride instead of distilling t-butyl chloride. Make sure a cork is kept in the test tube at all times because t-butyl chloride is volatile.
Data:
Volume of t-butyl alcohol | 5 mL | Weight of t-butyl chloride | 3.5 mL | % yield | 60.34 % | RI of t-butyl chloride | 1.383 |

Results/Discussion: When comparing the values of the literature IR and RI(Refractive Index) for tert-butyl chloride, the IR shows some similar peaks, however, the numbers are off by a few cm^-1. The RI also differs by 0.045. This shows that t-butyl chloride contains some impurities. The low percent yield can be the result of the solution of t-butyl chloride being extremely volatile. Therefore, the maximum amount of t-butyl chloride was not obtained.
Conclusions:
Tert-butyl alcohol is successfully converted to tert-butyl chloride with a yield of 60.34%.

Calculations

References
2-Chloro-2-methylpropane. Chemblink.com. 2011. Web. 09 October 2011.
Chemical Book. Chemicalbook.com. Web. 09