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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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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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 0.001988 C14H14O2 40.02 136-138 Spectral Analysis IR Absorption (cm-1) Assignment Benzoin 3411‚ 3374 OH 2961‚ 2903 C-H aromatic 2358 C-O
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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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in the subsequent reaction. The multistep synthesis of benzilic acid begins with a conversion benzaldehyde to benzoin through a condensation reaction. The benzoin then oxidizes into benzil‚ which undergoes rearrangement to give benzilic acid. Benzoin Synthesis * When two benzaldehyde molecules condense in the presence of thiamine‚ it leads to the formation of a molecule of benzoin. The thiamine behaves as a coenzyme catalyst. This step of the reaction involves the addition of ethanol and sodium
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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% and
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benzaldehyde to yield benzoin. Thiamine catalyst along with water and ethanol were added to the benzaldehyde‚ then NaOH was added until the solution turned yellow. After recrystallization‚ the product was benzoin. Step two was the oxidation of benzoin to benzil. Nitric acid was added to the benzoin and heated‚ this was followed by recrystallization to yield the benzil. In step three the benzil from step two was to be synthesized tetraphenylcyclopentadienone. The benzil and 1‚3-diphenylacetone
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of the first step‚ Benzoin‚ is provided thereby omitting the first step involving the conversion of benzaldehyde. For this experiment‚ the microscale techniques of reflux‚ crystallization‚ and melting-point determination were used. Utilizing these techniques a product yield of 93% for benzil and 57% for Benzilic acid was obtained‚ as well as a melting point range of 94.8 – 95.4oC for benzil and 152.0 – 153.9oC for Benzilic acid. With the literature melting-point value of benzil being 95oC ( Pavia
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