), Reactivity in molecular crystals, VCH, Weinheim 1993, p.177. 655-48-1 [Online]; ChemDoor: 2011. http://www.chemdoor.com/cas/655-48-1.html (Access 3/2/2014). The sodium salt of 5,5-diphenylhygantion, Dilantin , is an anticonvulsant used for the treatment of epilepsy. in the fume hood. University of Oklahoma. To this, a stirbar and 20 mL ethanol were added. M. Epple, S. Ebbinghaus, A. Reller, U. Gloistein and H. K. Cammenga, Thermochim. S. M. Sarge, E. Gmelin, G. W. H. Höhne, H. K. Cammenga, W. Hemminger and W. Eysel, Thermochim. After forming the meso hydrobenzoin product, the acetal derivative was formed. Soc.
Lab report- sodium borohydride reduction of a ketone. Reduction_of_Benzoin_post_lab_ - Name Esther Darfour Report Submission Date Experiment Title Sodium Borohydride Reduction of Benzoin Section Day and, 5 out of 5 people found this document helpful, Your TA will assign the technique points when they grade the, The purpose of this lab is to reduce using metal hydride sodium borohydride to, produce 1,2-diphenylthane-1,2-diol. dissolving metal reduction) In this experiment you will investigate the second example and look at the selectivity of a hydride reduction. The soluble benzophenone ketyls can be formed as radical anion by one-electron reduction of carbonyls with sodium. 1 Experiment 15: Reduction and Oxidation of Organic Compounds Part 1. This reaction mixture was then left to stir for another fifteen minutes. by cooling the beaker in an ice bath. Course. Stereospecificity is the property of a certain reaction mechanism the results in the formation of particular stereoisomeric products. The control of the pH value is the key to the benzoin condensation of benzaldehyde. Keep the Because of its high boiling point, Procedure In a 50 mL Erlenmeyer flask, dissolve about 0.500 g (note the actual amount used) of fluorenone in 8 - 10 mL of methanol. The solvent was then removed to leave an oily residue. The mixture was then poured into a suction filtration apparatus to allow for drying. After formation of the precipitate, the reaction mixture was left to stir for fifteen minutes.
A stereospecific mechanism explicitly defines the stereochemical outcome given a specific reactant. If the (+/-) hydrobenzoin products were formed, the resulting acetal derivative would show no distinction between the two methyl groups. 1959, 81, 2748. Chem. Chem. Stereochemical Analysis of Benzil Reduction, http://www.sigmaaldrich.com/catalog/product/aldrich/294535, http://www.chemdoor.com/cas/655-48-1.html, http://pubs.acs.org/doi/abs/10.1021/jf60176a035. F �5���t�����f`[� �p�ŝ1���q 225 0 obj <>stream
The usual procedure (and the one employed in thi sex periment) involves dissolving the borohydride in 95% ethanol and adding the carbonyl compound to this solution. Journal of Thermal Analysis and Calorimetry 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. Given a single, stereoisomerically pure starting material, or a mechanism in which a certain stereoisomer is energetically favored, the stereospecific will result in the formation of a single stereoisomer. Sodium borohydride, sodium hydroxide and hydrochloric acid are corrosive; if any of these solutions come in contact with your skin, rinse immediately with cold running water. 2. Sodium borohydride, a representative borohydride reagent, behaves as an effective source of nucleophilic hydride in an aprotic polar solvent, such as DMSO, sulfolane, HMPA, DMF or diglyme, and is used for the reduction of alkyl halides.93,94 As shown in Table 3, primary and secondary iodides, bromides and chlorides are converted to hydrocarbons at temperatures between 25 and 100 °C using sodium borohydride. to the borohydride solution while stirring the mixture continuously. Spring 2014. 2. This is a preview of subscription content, log in to check access. by controlling the rate of addition and By forming this acetal derivative of the hydrobenzoin product, the stereochemistry can be determined using a simple 1H NMR. Many drug manufacturing processes utilize stereospecific reagents in order to increase the overall yield and to decrease overall cost of the manufacturing procedure. Finally, the reaction mixture was diluted with 10% potassium bicarbonate. Finally the sidearm flask was cleaned and dried and weighed. Name: Esther Darfour Report Submission Date: 11/08/19 Experiment Title: Sodium Borohydride ( See also: Prepara... Propose 1. The acetal derivative of the hydrobenzoin product formed an oil, and a percent yield and 1H NMR of this product was able to be acquired. Introduction: The most common and useful reducing agents for reducing aldehydes, ketones, and other functional groups are metal hydride reagents. There are four main peaks that correspond to the product formed. Once the hydrobenzoin product was collected and dried, a percent yield and melting point range was obtained. The reduction of an aldehyde or ketone with sodium borohydride is straight forward and usually affords a high yield of the alcohol.
Although it could The third step is a condensation reaction of benzil with dibenzyl ketone (1,3-diphenyl-2-propanone) to produce tetraphenylcyclopentadienone. Solids, 8 (1990) 115. B. S. Goud and G. R. Desiraju, J. Chem.
The solvent-free reduction of benzophenone and five substituted benzophenones with sodium borohydride to the corresponding alcohols was studied by thermal analysis, X-ray powder diffractometry, NMR spectroscopy, and scanning electron microscopy. Because ethanol, the reaction solvent, is 2) Hydrobenzoin (racemic); CAS No. Stereochemical Analysis of Benzil Reduction. This was then left to stir for an additional fifteen minutes.
The melting point range of the hydrobenzoin product was found to be 136.1– 136.5 OC (Lit.1 137 – 139 OC). 1) Meso-hydrobenzoin; MSDS No.294535 [Online]; Sigma Aldrich: May 18, 2012. http://www.sigmaaldrich.com/catalog/product/aldrich/294535 (Accessed 3/2/2014). 1H NMR spectrum obtained on a 200 mHz NMR in CDCl3. T. L. Threlfall, Analyst, 120 (1995) 2435.
J. Janek and C. Korte, Solid State Ionics, 85 (1996) 305.
2. This step is used to neutralize any acid in solution, because the acetal that is formed is stable to base hydrolysis. S, (1995) 244. This is because when the sodium borohydride attacks the camphor, it would attack in the endo-phase due to the steric strain caused by the two geminal methyl groups on one side of the cyclohexane ring. Course Hero is not sponsored or endorsed by any college or university. 211 0 obj <>/Filter/FlateDecode/ID[<5AB6024AFD04A141B9A438312DD1374E>]/Index[188 38]/Info 187 0 R/Length 110/Prev 313763/Root 189 0 R/Size 226/Type/XRef/W[1 3 1]>>stream
This final product was formed so as to more easily identify the stereochemistry of the hydrobenzoin product. (Figure 7) The peaks at δ 1.677 and 1.906 ppm correspond to the two methyl groups attached to the acetal. By finding this melting point it could be inferred that the meso hydrobenzoin product had been formed, but a 1H NMR of the product could provide more evidence of the formation of this specific product. 5) Klein, D. Organic Chemistry John Wiley & Sons, Inc.; Hoboken, New Jersey 2012. In applications like pharmaceuticals and various amino acids used in biological systems only utilize one of the stereoisomers. University. completed, allow the mixture to stand at room temperature for 15 minutes with
This series of reactions (Figure 1) were carried out first using benzil and sodium borohydride to form the hydrobenzoin product, then the hydrobenzoin product was combined with anhydrous acetone and iron trichloride to form the product (4S-5R)-2,2-dimethyl-4,5-diphenyl-1,3-dioxolane. Chem. Journal of Thermal Analysis and Calorimetry 52, 165–176 (1998). The percent yield was found to be 60.62%, and the melting point range was found to be 136.1 -136.5 OC.
(4S-5R)-2,2-dimethyl-4,5-diphenyl-1,3-dioxolane. Chemical and sensory data supporting the difference between the odors of the enantiomeric carvones. product.). Iron trichloride acts as a lewis acid in this mechanism allowing for the nucleophilic addition of the diol.
Pre-Lab Complete the pre-lab assignment in WebAssign. Heat the mixture to boil on a Chem., 98 (1994) 1365. Procedures taken from Dr. Burlingham6. reaction has been completed, the excess borohydride and the Acta, 248 (1995) 1. Cram, D.J. 2018/2019. Below a mechanism that is consistent with this conclusion is shown (Figure 8). Next, 0.114 g of sodium borohydride was added in four parts to the mixture.
portion of diethyl ether. The reaction between sodium borohydride and Combine the ether extracts and wash them with an equal volume of The D... Rayon is a manufactured regenerated cellulose fiber. Send your donation to the Bitcoin address: Synthesis of p-nitroacetanilide-Nitration-Lu Le Laboratory, Synthesis of Chloroform from Acetone and Bleach - Haloform Reaction - Lu Le Laboratory, Preparation and Standardization of 0.1M Sodium Thiosulfate - Lu Le Laboratory, Preparation of 5,5-diphenylhygantion - Synthesis of Dilantin - Lu Le Laboratory, Kinetic Studies on Saponification of Ethyl Acetate by the Conductance Method - Physical Chemistry, Synthesis of 2-Methyl-2-Hexanol-The Grignard Reaction-Lu Le Laboratory, Sodium Borohydride Reduction of Acetophenone - Lu Le Laboratory, The Diels-Alder Reaction of Anthracene with Maleic Anhydride - Lu Le Laboratory, Preparation of Benzoin - Synthesis of Dilantin - Lu Le Laboratory, Synthesis of Rayon - Fibers - Lu Le Laboratory. L. Addadi, M. Cohen, M. Lahav and L. Leiserowitz, J. Chim. small-scale reaction such as in this experiment, the ethanol can be boiled away H. Schmalzried, Chemical Kinetics of Solids, VCH, Weinheim 1995. Chim. Learn more about Institutional subscriptions. Correspondence to
The Diels-Alder reaction is a cycloaddition reaction, a reaction in which two molecules undergo addition to yield a cyclic product. %%EOF
Prior to beginning the experiment, all glassware was placed in oven to ensure they were dry before use. K. Bowden and M. Hardy, Tetrahedron, 22 (1966) 1169. N. B. Singh and R.J. Singh, React. 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. Place 380 mg (0.380 g) of vanillin in a clean 5 mL conical reaction vial containing a spin vane. The two most common hydride reagents in organic chemistry are lithium aluminum hydride (LiAlH 4) and sodium borohydride (NaBH 4. The blogger spend time to maintain contents of this scientific website to share the joy of studying natural science. This formed an oil which was able to be run in the NMR, and a useful 1H NMR spectrum was acquired. Your TA should have graded the prelab before you began the. Chem. 1H NMR (200MHz, CDCl3) δ 1.677 ppm (s, 3H), 1.906 ppm (s, 3H), 5.574 ppm (s, 2H), 7.088 ppm (m, 10 H). acetophenone is exothermic. Bunsenges. N. B. Singh, R. J. Singh and N. P. Singh, Tetrahedron, 50 (1994) 6441. Ed. Below a mechanism that is consistent with this conclusion is shown (Figure 8). 3) Leitereg, Theodore J. et al. In order to raise the efficiency of the first reaction, the time over which the sodium borohydride was added and the time over which the reaction mixture was allowed to stir could be increased in order to ensure that more of the sodium borohydride had reacted with the benzil. Food Chem., 1971, 19 (4), pp 785–787. Rev. Weight 4.0g of acetophenone into D.C. Wigfield, Tetrahedron, 35 (1979) 449. 4) Todd, D. J. Chem. And the 1H NMR (200 MHz, CDCl3), Table 1, was utilized to characterize this acetal derivative of the hydrobenzoin. (Too much product would be lost in the aqueous ethanol layer.) This reaction resulted in the formation of 0.43 g product. In general, chemists must use similar chemical reactions in order to better understand the mechanisms involved in various processes.
The percent yield was found to be 73.33%. 188 0 obj <> endobj
Since the thiazole ring is broken easily in basic solution, both the aqueous solutions of thiamine hydrochloride and sodium hydroxide should be cooled thoroughly with an ice bath before use.
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