Thiamine-Catalyzed Benzoin Condensation I.Conclusion Benzoin was produced by reacting 2 mols of benzaldehyde with the catalyst thiamine to form a new C-C bond. A total of 2.626 grams were recovered. There was a 33% recovery of benzoin. The low percent recovery could be due to the purity of the limiting reactant‚ benzaldehyde. Upon filtration‚ the mother liquid appeared oily making it more likely that the low recovery was due to the solution ‘oiling out.’ This could be avoided in the future
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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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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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Spectra Analysis Organic Chemistry Lab‚ CHEM 369 The University of Tennessee‚ Knoxville Dr. Smith Spectra 1: tert-butyl cyanoacetate Molecular formula: 141/13 = 10 R 11 => C10H10+11 => C10H21 C10H21NO2 – C3H10 = C7H11NO2 DBE: 2(#C - #H/2 - #X/2 + #N + 2)/2 =2(7 – 11/2 – 0/2 + 1 + 2)/2 = 3=> 1 double bond and 1 triple bond Mass spectrum table: m/z fragment |40
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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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material 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
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tetraphenylcyclopentadienone from benzaldehyde and to run reactions on carbonyl containing compounds. There was a total of three steps that led up to the synthesis of the final product‚ tetraphenylcyclopentadienone. The first step of the experiment was the condensation of 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
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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 ‚‚which represents and OH functional group. The second step of the reaction was to oxidize benzoin to form benzil; this reaction yielded 27.04% benzil. The MP of the benzil was 91O-93O C and the IR spectra revealed
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mls/student)‚ benzaldehyde (4 mls/student) wk 2: 95% ethanol (30 mls/student) wk 3: acetic acid (6 mls/student)‚ ammonium nitrate (1 g/student)‚ 0.1g/ml cupric acetate (1.5 mls/student)‚ dichloromethane (6 mls/ student)‚ 30% acetone in heptanes (3 mls/student)‚ 95% ethanol (20 mls/student) wk 4: 1‚3 diphenylacetone (0.5 g/student)‚ triethylene glycol (5 mls/student)‚ 40% benzyltrimethylammonium hydroxide/methanol (0.5 mls/student) Part A: Thiamine catalyzed condensation benzoin condensation
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54.4% 15.765 g Melting Point of Intermediate (Benzoin) Melting Point of Product (Benzil) Trial 1 – 129-131°C Trial 2 – 133-135°C Trial 3 – 132-135°C Trial 1 – 92-93°C Trial 2 – 92-94°C Trial 3 – 93-95°C Average Melting Point Observed (Intermediate): 131.3-133.6°C Average Melting Point Observed (Product): 92.3-94°C Theoretical Melting Point of Benzoin: 132°C Theoretical Melting Point of Benzil: 94.5°C Discussion and Conclusions:
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