Sample Laboratory Report: Conversion of Bromocylopentane to Cyclopentanol Using the S N 2 Reaction Cover Page: Conversion of Bromocylopentane to Cyclopentanol Using the S N 2 Reaction by Ezra Cornel Lab Instructor: Andrew D. White July 04, 2008 Balanced Reaction: Br 1 +1 NaOH H 2 O OH +1 1 NaBr Mechanism of Reaction: Br H NaOH OH H Results and Discusion: The product was isolated by thre extractions with ether from the aqueous reaction mixture. The product was a colorles liquid with a faint swet smel. An IR spectrum of the product (liquid suspension) was obtained (se atached) and the refractive index was measured. Refractive Index Product: n 20/D = 1.450 (Literature 1.453 1 ). Theoretical and Percent Yield % Yield = Theortical Yield = 5.0 gCyPentBr x 1 mole CyPentBr 49 g x 1 mole CyPentBr 1 ole yentOH x 1 mole CyPentOH 86 g Theortical Yield =2.8 gCyPentOH 2.01 gCyPentOH obtained .8 et expcte x 10 = 69. % Conclusion: The measured refractive index is consistent with the identification of the product as cyclopentanol. The refractive index of the starting material, bromocylopentane, is reported as 1.4885 2 . The IR spectrum is also consistent with the identification of the product as cyclopentanol. The broad absorption betwen 3200-3600 cm -1 , acompanied by the sharp absorption at 3626 cm -1 , are consistent with an O-H stretch. The strong absorption at 2962 cm -1 is consistent with an sp 3 C-H stretch. Additionaly, the medium absorption at 994 cm -1 is consistent with a C-C stretch. The percent yield of the reaction was 69.6 %. This yield was lower than expected due to the loss of sample during the extraction proces. An emulsion formed during the extraction and while it was broken up, the layers were hard to separate and product was likely lost in the aqueous layer. IR Spectrum 3 : Note: A copy of your actual IR should be included in this section. A literature example is included here only for ilustration purposes. You may include literature examples of spectra in your report to further support your conclusions (remember to include the URL?s and details of the spectra in your bibliography). sp3 C-H O-H C- Bibliography (this can be concise and we wil not grade on format, so long as the information is accurate and your TA can figure out what material you used.) 1 Aldrich Handbook of Fine Chemicals, p 1312 (2007-2008). 2 Merck Index, 11 th edition, p 867 (1989). 3 http:/riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng, IR Cl 4 Solution, acesed 1.9.09. Thomas Ruttledge C2510 Sample Laboratory Report
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