CH243 Organic Chemistry Laboratory

Thompson

Working Notes Experiment 15: Carbonyl Chemistry: Thiamine-Mediated Benzoin Condensation of Furfural
Introduction In this reaction two benzaldehyde molecules will react (condensation) to form benzoin using vitamin B1 (thiamine) as a catalyst. Condensation reactions like this have high atom economy, but have traditionally required highly toxic cyanide salts as catalysts. Replacing dangerous cyanide salts with the safe, biologically derived thiamine is a significant green enhancement to the reaction. Note that this is a two-week experiment as the reaction rate is slow so we will start the reaction week one and do the workup and purification week two. Techniques Melting Point Determination (Chapter 12) Recrystallization (Chapter 13) Reading Notes Prepare the reaction in the mini-hoods to minimize exposure. The product will be characterized by melting point and infrared spectroscopy. Experiment Report For this experiment I would like you to create a summary report. The report should be a typed one-page narrative and should include: A brief summary of your results including o Percent yield of furfural product. o Atom economy for this reaction o Yield economy (% yield * atom economy) Analyze the quality end error of your experiment. o Melting point (or range) of your product. o Did the experiment go well or poorly and can you explain what went wrong? Do you find your results to be reliable? Evaluate this experiment in terms of its greenness. o Give a brief overall analysis of the greenness of this reaction o What recommendations do you have to improve the green character of this reaction? Attach a copy of your IR (another copy should be taped in your notebook).

Working Notes Experiment 15

CH243 Organic Chemistry Laboratory

Name____________________

Experiment 15: Carbonyl Chemistry: Thiamine-Mediated Benzoin Condensation of Furfural

Pre-laboratory Questions 1. Give the balanced equation for this reaction.

2. Describe the role of sodium hydroxide in this reaction?

3. Complete the following tables of chemical data: Compound M.M. Sol. m.p. b.p. (g/mol) (C) (C) Thiamine hydrochloride Water Ethanol Sodium hydroxide Furfural Furoin

D (g/mL)

4. Consider the chemicals used for this experiment. What realistic hazards are present? What safety procedures are necessary beyond wearing goggles and gloves?

Working Notes Experiment 15