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Benzoin Condensation

Condensation of aldehydes . Oxidatively balanced process. Acyloins are componds which have a hydroxyl group to a carbonyl group

Important in biochemical processes (pyruvate dehydrogenase, etc.).

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Benzoin Condensation: Mechanism

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Step 1: Dissolve 1.3 g of thiamine hydrochloride in 4 mL water in a 50 mL EM flask. Add 15 mL 95% ethanol and cool the solution in ice bath.
95% ethanol (15 mL)
Thiamine hydrochloride (1.3 g) 4 mL water

Cool in ice bath

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Step 2: To the above solution, add 2.5 mL of 3M sodium hydroxide solution drop wise while swirling. Make sure that the temperature does not rise above 20 oC.

2.5 mL 3M NaOH; dropwise addition while swirling Solution from step 1 Temperature < 20 oC

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Step 3: Add 7.5 mL pure benzaldehyde to the above solution (yellow!) and heat the solution at 60 oC for 1 1.5 h.
7.5 mL pure benzaldehyde Yellow solution from step 2

Heat at 60 oC for 1 to 1.5 h

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Step 4: Cool the solution in an ice bath. If crystallization does not occur, you may need to scratch the flask (inside!) with a glass rod to induce crystallization. Step 5: Collect the product by suction filtration and wash it free of yellow mother liquor with 1:1 mixture of 95% ethanol and water. Properties of the product Color: Colorless Melting Point: 134 oC 135 oC

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Atom Economy
Atom Economy (Efficiency): A measure of the efficiency (greenness) of a chemical process Percent Yield (Fractional): A measure of the effectiveness of a chemical process

Chemical processes can be effective and inefficient

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Principles of Green Chemistry

Prevention: Better to prevent waste than to treat or clean up waste after it is formed. Atom Economy: Synthetic methods should be designed to maximize the incorporation of all materials
used in the process into the final product.

Less Hazardous chemical synthesis: Whenever practicable, synthetic methodologies should be

designed to use and generate substances that posses little or no toxicity to human health and the environment.

Designing Safer Chemicals: Chemical products should be designed to preserve efficacy of function
while reducing toxicity.

Safer Solvents and Auxiliaries:

The use of auxiliary substances (i.e. solvents, seperation agents, etc.) should be made unnecessary whenever possible, and innocuous when used.

Design for NRG Efficiency: Energy requirements should recognized for their environmental and
economic impacts and should be minimized. Synthetic methods should be conducted at ambient temperature and pressure.

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Principles of Green Chemistry

Use of Renewable Feedstocks: A raw material or feedstock should be renewable rather than
depleting, whenever technically and economically practicable.

Reduce Derivatives:

Unnecessary derivatization (blocking group, protection/deprotection, temporary modification of physical/chemical processes) should be avoided whenever possible.

Catalysts: Catalytic reagents (selective as possible) are superior to stoichiometric reagents.

Design for Degradation:

Chemical products should be designed so that at the end of their function they do not persist in the environment and break down into innocuous degradation products.
Analytical methodologies need to be further developed to allow for real-time, in-process monitoring and control prior to the formation of hazardous substances.

Real-Time Analysis for Pollution Prevention:

Inherently Safer Chemistry for Accident Prevention: Substances and the form of a
substance used in a chemical process should be chosen so as to minimize the potential for a chemical accidents, including releases, explosions, and fires.

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