SYNT m o d u l a r · l a b o r a t o r y · p r o g r a m · i n · publisher: H. A. Neidig c h e m i s t r y 738 organic editor: Joe Jeffers Copper-Catalyzed Oxidation of Benzoin to Benzil prepared by Carl T. Wigal‚ Lebanon Valley College PURPOSE OF THE EXPERIMENT Oxidize benzoin to benzil using ammonium nitrate and copper(II) ion as a catalyst‚ monitoring the reaction by thin-layer chromatography. Characterize the product using melting point measurement and infrared spectroscopy. EXPERIMENTAL
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Introduction: The purpose of this experiment is to use sodium borohydride to reduce benzil. However‚ stereochemistry allows for five possible products. If only one carbonyl group is reduced during the reaction a racemic mixture of benzoin will be the product that is produced. After the first reduction a chiral center forms causing the second reduction to occur from only one side of the ketone. Depending on which side the second reduction take place there are three possible products including: a racemic
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Synthesis of Benzoin Date of Experiment: 1-26-15 Chelsea Price Lab Partner: Joey Simmons Abstract: In this experiment‚ benzoin was synthesized from benzaldehyde‚ using thiamine hydrochloric acid as a catalyst. The thiamine HCl was deprotonated by sodium hydroxide and acted as a nucleophile to attack the benzaldehyde. A water-cooled condenser was used to heat the solution at reflux. Vacuum filtration was used to wash and dry the product. The benzoin product was recrystallized
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Benzil is produced in the first step of this experiment’s multistep synthesis through the oxidation of benzoin. In order to produce the desired o-diketone‚ the alcohol on benzoin must be oxidized. Nitric acid was the oxidizing agent used in this experiment. As a result‚ the alcohol group on benzoin acted as the nucleophile and attacked the electrophilic nitrogen of nitric acid. As this step forms oxonium‚ excess water in the system deprotonated the oxonium to restore the neutral charge on oxygen
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Benzil Reduction Introduction The objective of the experiment was to reduce Benzil‚ using sodium borohyride as the reducing agent. In a benzil reduction‚ there are five possible products than can occur‚ specifically a racemic mixture of benzoin‚ racemic mixture of hydrobenzoin‚ or meso-hydrobenzoin. Therefore‚ three different tests were conducted in determining the identity of the product: melting point‚ thin light chromatography‚ and infrared spectroscopy. (a) Mechanism and reaction equation
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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. This two-step reaction reduces aldehydes by hydrides to primary alcohols‚ and ketones to secondary alcohols. In order for the reaction to occur and to better control the stereochemistry and yield of the product‚ the metal hydride nucleophile of the reducing agents such as LiH‚ LiAlH4
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Aim Synthesis of Meso-1‚2-diphenyl-1‚2-ethanediol with focus on stereoselectivity Method Please refer to the CEM3005W practical manual for details on experimental procedure. Results and Analysis {Limiting reagent} Mass benzoin = 2.0050g (0.00945 mole) Mass sodium borohydride = 0.4059g (0.0107 mole) Mass compound A used to form compound B = 1.0647g Results Mass (g) moles Molecular formula Yield (%) Mp (pure) Compound A 1.7458 0.00815 C14H14O2 86.22 138-139 Compound C 0.4255
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Synthesis of benzilic acid from benzoin utilizing a multi-step reaction. Names: Arian Karim TA Name: Sayantan Das Lab Day & Time: Thursday 7:30-11:40 Lab Section #: Abstract The main purpose of this experiment was to synthesize benzilic acid from benzoin. This requires a multistep synthesis with benzyl as an intermediate product. The first step required HNO3 as an oxidizing agent and the second step required KOH and HCl. The percentage yields of benzil and benzilic acid were 59.5%
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Results: Limiting Reactant: Eq 1 Limiting reactant = Benzoin Theoretical yield of Benzil: Eq 2 Theoretical Yield Benzil | 0.296 g | Mass of Crude Benzil | 0.188 g | Mass of Final Benzil | 0.127 g | % Yield | 43% | % Recovery | 66% | Table 1: Mass of crude/final Benzil‚ % yield‚ and % recovery Percent Yield: % Yield = (Final product/Theoretical product) x 100 Eq 3 = (0.127 g/0.296 g) x 100 = 43% yield Percent Recovery
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Multistep Synthesis of Tetraphenylcyclopentadienone Author: Instructor: Date work performed: 10.18.2012--10.25.2012 Date work submitted: 11.01.2012 Abstract: The aim of this experiment was to perform a multistep synthesis to form tetraphenylcyclopentadienone. The first step of the reactions was to synthesize benzoin from the condensation of benzaldehyde. A yield of 28.91% benzoin was obtained. The MP of benzoin was 127O-130O C and the IR spectra displayed a carbonyl peak at 3415 cm-1
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