Benzoin Condensation

Benzoin Condensation - Benzoin Condensation Tore...

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Benzoin Condensation Tore Maras-Lindeman Drawer: U33A TA: Matthew Fields • University of Kentucky-Department of Chemistry• April 11, 2011 Tore Maras-Lindeman • tmli222@uky.edu • University of Kentucky Department of Chemistry
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Table of Contents Benzoin Condensation 2 Purpose 2 Theory 2 Results and Discussion 5 Theoretical Yield of Benzoin 5 Percent Yield 5 Melting point of benzoin 6 IR examination 6 Conclusion 7 Waste Disposal 7 Appendix A - IR Spectrum 8 Bibliography 9 Tore Maras-Lindeman • email: tmli222@uky.edu • University of Kentucky Department of Chemistry 1
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Benzoin Condensation Condensation without the production of water or alcohol ? Purpose The synthesis of benzoin from benzaldehyde with an appreciable yield in order to understand the role of cyanide ions as a catalyst during this reaction was the purpose of this experiment(Mayo 2010 ). Theory Condensation(Steven F. Pedersen 2010) without the production of water or alcohol seems erroneous, but in fact condensation is what this type of reaction is. Basically, benzoin is an α - hydroketone which manifests due to the dimerization the (Smith 2009) aromatic aldehyde, benzaldehyde. In this experiment, benzaldehyde acts like both a nucleophile and an electrophile and its dimerization occurs in the presence of a catalytic cyanide ion. In other words this is a cyanide-catalyzed benzoin condensation where we observe the reaction of two moles of benzaldehyde that in turn forms a new carbon carbon bond yielding benzoin, coined as condensation. Cyanide has a high nucleophilic efficiency. This efficiency is due to low steric hindrance and ease of polarisability(Steven F. Pedersen 2010). CN - is a strong nucleophile it must be understood that cyanide itself stabilizes, that is, a resonance stabilized carbanion which is an intermediate carbanion of which CN - is a good leaving group(Steven F. Pedersen 2010). This resonance stabilized carbanion is a strong nucleophile and attacks the carbonyl of benzaldehyde. In the same way of a Gringard Reaction (Timberlake 2010)CN
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Benzoin Condensation - Benzoin Condensation Tore...

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