Leave this section blank in your post-lab report. Correspondence to F �5���t�����f`[� �p�ŝ1���q - 66.198.246.17. The Benzophenone/Ketyl Tetrahydrofuran(THF) Still 1. This can be explained by examining Figure 5. product.). Below a mechanism that is consistent with this conclusion is shown (Figure 8). Engl., 34 (1995) 1171. The aromatic nitration of acetanilide is an exothermic reaction ; the temperature must be carefully controlled by... Chloroform is an organic compound with formula CHCl 3 . Reduction of a ketone using sodium borohydride. Educ. 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. View Lab Report - Reduction_of_Benzoin_post_lab_ from CHEM 269 at University of Massachusetts, Amherst. Filter the dried solution into a round-bottom flask. D. Giron, Thermochim. N. B. Singh and R.J. Singh, React. sodium borohydride reduction of a ketone . ; Kopecky, K.R. Vicinal dihalides, such as 1,2-dibromooctane, are smoothly converted to the correspondin… Reduction of Benzyl Written by x TA x Lab Section x Date x Introduction Figure 1 Mechanism Reaction for the reaction with NaBH4 Procedure Refer to lab manual. Therefore, it is important to add the acetophenone Nevertheless, this reaction can be carried out without the need for a solvent, leading to pure alcohol without side products. Soc., Dalton Trans., (1996) 11. G. W. H. Höhne, H. K. Cammenga, W. Eysel, E. Gmelin and W. Hemminger, Thermochim. This reaction resulted in the formation of 0.43 g product. Transfer the mixture in a The flask was then placed in a hot bath for 2 minutes. chm1321 lab 4: Reduction of Benzyl . Jpn., 63 (1990) 290. Since the 1H NMR of all of the stereoisomers of hydrobenzoin are nearly indentical, an acetal derivative of the product was formed (Figure 4).
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. Then, the solution was cooled and poured into a separatory funnel containing 5 mL of 10% aqueous potassium carbonate. In order to accurately determine the stereochemistry of the product or products formed, a derivative of the hydrobenzoin, with a distinct NMR must be made. In this experiment, the reduction of Benzil using sodium borohydride was run in order to determine whether the reaction was indeed stereospecific. thisproblem, the first step in the work-up is to boil off much of the ethanol. In general, chemists must use similar chemical reactions in order to better understand the mechanisms involved in various processes. This reaction resulted in the formation of 1.03 g of product. Chem 269 Sodium Borohydride Reduction of Benzoin Formal Report.docx, Sodium Borohydride Reduction of Benzoin.docx, University of Massachusetts, Amherst • CHEM 269, University of Massachusetts, Amherst • CHEM MISC. Air was continuously pulled through the sidearm flask until the petroleum ether evaporated and an oil was left behind. 0
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Place 380 mg (0.380 g) of vanillin in a clean 5 mL conical reaction vial containing a spin vane. Chem., 102 (1990) 1363. After the There are four main peaks that correspond to the product formed. a conic flask and prepare an ice bath. V... Benzoin is the precursor of the antiepileptic medicine, Dilantin (Phenytoin) . Chem.
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Introduction The benzophenone-sodium still is a widely used method to produce moisture, oxygen, and peroxide free organic solvents, especially for tetrahydrofuran (THF). Add the acetophenone dropwise Chem. https://doi.org/10.1023/A:1010126626572, DOI: https://doi.org/10.1023/A:1010126626572, Over 10 million scientific documents at your fingertips, Not logged in Pre-Lab Complete the pre-lab assignment in WebAssign. 4). This conclusion provided evidence that the meso hydrobenzoin product had been formed exclusively in the first step of the experiment. Res. The reaction mechanism is shown in Figure 9. Sodium borohydride is considered to be a selective reagent, 31 which means that it is a weaker reducing agent when compared to LiAlH 4 (e.g., see Section 7.6).Sodium borohydride is useful for the reduction of aldehydes, ketones, or acid chlorides in the presence of other easily reducible functional groups. -it is exothermic addition of benzophenone should not be too rapid because minimizes side reaction of sodium borohydride with solvent methanol. Hydrogen gas is highly flammable. 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. The percent yield was found to be 60.62%, and the melting point range was found to be 136.1 -136.5 OC. The Sodium Borohydride Reduction of Benzil and Benzoin The reduction of benzoin produces three stereoisomeric hydrobenzoin products: a (1R, 2R) isomer, a (1S, 2S) isomer, and a meso compound. The two most common hydride reagents in organic chemistry are lithium aluminum hydride (LiAlH 4) and sodium borohydride (NaBH 4. Sodium borohydride Reduction of Benzil Introduction: The Purpose of this experiment is for the students to learn how to use sodium borohydride to reduce benzil to its secondary alcohol product via reduction reaction. evolved, this treatment with acid must be carried out in a fume hood or a very [Online] 1971, J. Agric. As noted before, depending on the stereoisomer of the hydrobenzoin, the acetal derivative could form two distinct stereoisomers (Figure 4). 225 0 obj
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Phys. Next, 0.114 g of sodium borohydride was added in four parts to the mixture. Acta, 219 (1993) 333. Mp 136.1-136.5 OC (Lit.1 137-139 OC. (4S-5R)-2,2-dimethyl-4,5-diphenyl-1,3-dioxolane. 2018/2019. volume 52, pages165–176(1998)Cite this article. In the second step, the benzoin is oxidized to benzil through the use of an oxidizing agent. 1979, 56 540; Rowland, A.T. J. Chem Educ. Combine the ether extracts and wash them with an equal volume of Soc. 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. ethoxyborohydridesare destroyed with aqueous acid. Acta, 248 (1995) 1. Then finally 4-5 drops of HCl were added to the reaction mixture until a white precipitate formed. K. Bowden and M. Hardy, Tetrahedron, 22 (1966) 1169. The unequal discount of narrow ketones has been attained through a countless of different approaches. by controlling the rate of addition and Stereospecific reactions cut down on the time and possible cost associated with separating the stereoisomeric forms in a reaction mixture. 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. Chemical and sensory data supporting the difference between the odors of the enantiomeric carvones. Because of its high boiling point, (Too much product would be lost in the aqueous ethanol layer.) Reduction of benzophenone with sodium borohydride lab report. Journal of Thermal Analysis and Calorimetry
The two most common metal hydride reagents are sodium borohydride (NaBH4) and lithium aluminum hydride (LAH, LiAlH. The melting point range of the hydrobenzoin product was found to be 136.1– 136.5 OC (Lit.1 137 – 139 OC). The blogger spend time to maintain contents of this scientific website to share the joy of studying natural science. F. Toda, in Y. Ohashi (Ed. The collected organic extracts were then combined and washed with 10 mL of water. well-ventilated room. By forming this acetal derivative of the hydrobenzoin product, the stereochemistry can be determined using a simple 1H NMR. �qƍ,L���0�`ig�̬P{�g�k�5C�#?c
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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. 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., 98 (1994) 1365. Res., 28 (1995) 193. Y. Ohashi (Ed. A stereospecific mechanism explicitly defines the stereochemical outcome given a specific reactant. Weight 4.0g of acetophenone into Procedures taken from Dr. Burlingham6. 2018/2019. 2, (1995) 325. Int. 1) Meso-hydrobenzoin; MSDS No.294535 [Online]; Sigma Aldrich: May 18, 2012. http://www.sigmaaldrich.com/catalog/product/aldrich/294535 (Accessed 3/2/2014). The ether extract is dried with either sodium sulfate or magnesium sulfate. Perkin Trans. R. Sato, T. Nagaoka, T. Goto and M. Saito, Bull. This step is used to neutralize any acid in solution, because the acetal that is formed is stable to base hydrolysis. 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. In applications like pharmaceuticals and various amino acids used in biological systems only utilize one of the stereoisomers. B. S. Goud, K. Panneerselvam, D. E. Zacharias and G. R. Desiraju, J. Chem. If the (+/-) hydrobenzoin products were formed, the resulting acetal derivative would show no distinction between the two methyl groups. M. Epple, S. Ebbinghaus, A. Reller, U. Gloistein and H. K. Cammenga, Thermochim. M. Epple and L. Tröger, J. Chem.
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