Lab Report 2 CHEM 3428 Section 002

Topics: Chemistry, Epoxide, NMR spectroscopy Pages: 7 (1312 words) Published: April 14, 2015
Epoxidation Reactions Lab Report 2
Abstract
An oxygen atom is transferred from a peroxy acid to the carbon=carbon double bond thus forming an epoxide.  Scheme 1. Oxone Epoxidation.Scheme 2. mCPBA Epoxidation.
The percent yield for the Oxone epoxidation reaction was 65% yield and the mCPBA epoxidation reaction was 70% yield. Oxone is the greener alternative because using mCPBA is twice as expensive as Oxone and leaves behind the epoxide plus m-chlorobenzoic acid while Oxone creates non-toxic byproducts and recycles acetone in the epoxidation reaction. Introduction

The epoxidation of an alkene creates an epoxide that is reactive to nucleophiles. This is important in organic chemistry as well as biological sciences. For example epoxide hydrolase aids in purification during drug metabolism. The mechanisms for Oxone and mCPBA epoxidation can be found in figures 1 and 2 below.

Figure 1. Oxone Epoxidation Mechanism. Figure 2. mCPBA Epoxidation Mechanism. There are twelve key principles of green chemistry that are used to evaluate how green a reaction may be. A green reaction prevents waste before it is created with little to no toxicity. Green experiments should be designed to maximize the starting materials into the final products while minimizing toxicity. Raw materials should be renewable and products should break down and not persist in the environment while reducing derivatives. All experiments should be performed in real time with use of catalysts while minimizing potential chemical accidents. Results and Discussion

The Oxone epoxidation reaction is a two-step mechanism that includes forming the dioxirane first. The second step is using the dioxirane to attack the trans-anisole. The mCPBA reaction is a one step that forms the trans-anethole oxide. The result of the Oxone epoxidation reaction yielded 0.96 g of product which was 65% yield. The result of the mCPBA epoxidation reaction yielded 1.03 g or product which was 70% yield. The product was identified via FTIR and 1H-NMR spectroscopy. The results of the FTIR and 1H-NMR spectroscopy for each reaction can be found in table 1-4 below. Table 1. 1H NMR Spectral Analysis of Trans-Anethole Oxide (Oxone).

Structure
1H NMR

Ha: ô = 7.19ppm, m (J = 8 Hz), (2 1H)
Hb: ô = 6.85 ppm, m (J = 8 Hz), (21H)
H1: ô = 2.16 ppm, m (J = 8 Hz), (1 1H)
H2: ô = 3.02-3.52 ppm, m (J = 8 Hz), (1 1H)
OCH3: ô = 3.79 ppm, s (J = 8 Hz), (3 1H)
CH3: ô = 1.01-1.43 ppm, s (J = 8 Hz), (3 1H)

Table 2. FTIR Analysis of Trans-Anethole Oxide (Oxone).
Structure
IR (cm-1)

ṽ = 1462.80 cm-1 (m) C–H bend alkanes
ṽ = 1515.53 cm-1 (m) C–C stretch (in–ring) aromatics
ṽ = 1613.08 (m) C–C stretch (in–ring) aromatics
ṽ = 2836.34 cm-1 (m) H–C=O: C–H stretch aldehydes
ṽ = 2964.49 cm-1 (m) C–H stretch alkanes
ṽ = 3480.45 cm-1 (s,b) O–H stretch, H–bonded alcohols, phenols

Table 3. 1H NMR Spectral Analysis of Trans-Anethole Oxide (mCPBA).

Structure
1H NMR

Ha: ô = 7.16ppm, m (J = 8 Hz), (2 1H)
Hb: ô = 6.85 ppm, m (J = 8 Hz), (21H)
H1: ô = 3.02-3.52 ppm, m (J = 8 Hz), (1 1H)
H2: ô = 5.28ppm, m (J = 8 Hz), (1 1H)
OCH3: ô = 3.79 ppm, s (J = 8 Hz), (3 1H)
CH3: ô = 1.14-1.44 ppm, s (J = 8 Hz), (3 1H)

Table 4. FTIR Analysis of Trans-Anethole Oxide (mCPBA).
Structure
IR (cm-1)

ṽ = 1463.15 cm-1 (m) C–H bend alkanes
ṽ = 1515.25 cm-1 (m) C–C stretch (in–ring) aromatics
ṽ = 1585.16-1612.97 cm-1 (m) C–C stretch (in–ring) aromatics ṽ = 1721.74 cm-1 (s) C=O stretch aldehydes, saturated aliphatic ṽ = 2836.28 cm-1 (m) H–C=O: C–H stretch aldehydes
ṽ = 2963.78 cm-1 (m) C–H stretch alkanes

The tables show that the final product of both reactions was Trans-Anethole Oxide. Conclusion
In conclusion both the Oxone and mCPBA experiments were successful. mCPBA reaction had a more successful percent yield of 70% while the Oxone reaction had a slightly less yield of 65%. The green chemistry analysis ruled Oxone as the greener experiment in comparison to mCPBA....

References: Anastas, P., & Warner, J. (1998). Chapters 1-4. In Green Chemistry: Theory and Practice. Oxford [England: Oxford University Press.
Rebecca S. Centko, Ram S. Mohan*. (2001). The Discovery-Oriented Approach to Organic Chemistry. W 4. Epoxidation of p-Methoxy-trans-beta-methylstyrene. Journal of Chemical Education, 78(1), 77-79. Retrieved March 1, 2014, from http://jchemed.chem.wisc.edu/
William C. Broshears, John J. Esteb, Jeremy Richter, and Anne M. Wilson*. (2004). Simple Epoxide Formation for the Organic Laboratory W Using Oxone. Journal of Chemical Education, 81(7), 1018-1019. Retrieved March 1, 2014, from www.JCE.DivCHED.org
Appendix
Appendix 1. Annotated FTIR Spectrum of Trans-Anethole Oxide (Oxone).
Appendix 2. Annotated FTIR Spectrum of Trans-Anethole Oxide (mCPBA).
Appendix 3. Annotated 1H NMR Spectrum of Trans-Anethole Oxide (Oxone).
Appendix 4. Annotated 1H NMR Spectrum of Trans-Anethole Oxide (mCPBA).
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