reduction of benzoin with sodium borohydride lab report conclusion
The reaction yields only the meso hydrobenzoin compound. portion of diethyl ether. The collected organic extracts were then combined and washed with 10 mL of water. Stereospecific reactions cut down on the time and possible cost associated with separating the stereoisomeric forms in a reaction mixture. Starting materials were obtained from the instructor and used without further purification. 1979, 56 540; Rowland, A.T. J. Chem Educ. Finally the sidearm flask was cleaned and dried and weighed. Then use TLC plate analysis to determine if benzoin has. The two Newman projections in (Figures 5 and 6) depict the stereochemical outcomes with respect to the ethane backbone within the molecule. Course Hero is not sponsored or endorsed by any college or university. Course. V... Benzoin is the precursor of the antiepileptic medicine, Dilantin (Phenytoin) . Chem., 98 (1994) 1365. Y. Ohashi (Ed. 2)      Hydrobenzoin (racemic); CAS No. Because ethanol, the reaction solvent, is The solution was heated gently and stirred until all of the Benzil had dissolved in the ethanol. View Lab Report - Reduction_of_Benzoin_post_lab_ from CHEM 269 at University of Massachusetts, Amherst. sodium. B. S. Goud and G. R. Desiraju, J. Chem. After the (An infrared spectrum can be used to determine if any ketone is present in the Reductions occur when hydrogen is incorporated into a functional group, either through high pressure hydrogenation using hydrogen gas and a metal catalyst or through a metal-hydride transfer reaction. J. M. Thomas, Pure Appl. The overall reaction was relatively simple and resulted in the formation of a stereoisomeric product that could be studied using NMR. When most of the ethanol has been removed, the product Heat the mixture to boil on a It is one of the four chloromethanes. To this, a stirbar and 20 mL ethanol were added. H. Schmalzried, Chemical Kinetics of Solids, VCH, Weinheim 1995. An alternative third step is the reduction of benzil to dihydrobenzoin with a reducing agent, sodium borohydride. 3)      Leitereg, Theodore J. et al. temperature of the reaction mixture between 30~50. On first glance, the reduction of benzyl using sodium borohydride could result in the formation of three different stereochemical products as shown in Figure 3. Weight 4.0g of acetophenone into The proton NMR along with the melting point range acquired, 136.1– 136.5 OC          (Lit.1 137 – 139 OC), for the hydrobenzoin compound helped to lead to this conclusion. a conic flask and prepare an ice bath. Biol., 83 (1986) 831. Extract aqueous layer with the diethyl ether and do it again with another Course. Acta, 269/270 (1995) 433. ( See also: Prepara... Propose 1. 188 0 obj <> endobj Perkin Trans. Filter the dried solution into a round-bottom flask. Engl., 34 (1995) 1171. Chem., 136 (1924) 329. Journal of Thermal Analysis and Calorimetry 52, 165–176 (1998). be vacuum-distilled, distillation could not separate it from unreacted starting acid to the reaction mixture. product.). H. K. Cammenga and M. Epple, Angew. In general, chemists must use similar chemical reactions in order to better understand the mechanisms involved in various processes. J. P. Dunitz and J. Bernstein, Acc. Mp 136.1-136.5 OC (Lit.1 137-139 OC. A melting point range was acquired for the hydrobenzoin product, while a 1H NMR was collected to determine if the intended final product was formed and moreover the stereochemical properties of the final product. material (if any) because the two compounds have boiling points only 1E apart. W. E. Brown, D. Dollimore and A. K. Galwey (Eds. Today, cutting edge research is being done to better explore the mechanistic pathways of numerous chemical reactions. CONCLUSION Benzil is a yellow solid and hydrobenzoin is white; therefore, the reduction reaction is evident by the color change This reaction of benzil with sodium borohydride to form hydrobenzoin is an example of a sodium borohydride reduction of a ketone to an alcohol. 2. H. Schmalzried, Ber. 3. Sodium Borohydride Reduction of Benzoin . Ed. 225 0 obj <>stream M. Epple. In order to determine which stereoisomer of the hydrobenzoin was formed, the Newman projections of both acetal derivatives must be compared to the 1H NMR.

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