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    Benzoin Condensation: - 1 - DE Jones

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    Liz Hackett
    The document describes the benzoin condensation reaction, which is the condensation of aldehydes in an oxidatively balanced process to form acyloins, compounds with a hydroxyl group bonded to a carbonyl group. It is an important reaction in biochemical processes like the pyruvate dehydrogenase reaction. The document also provides the experimental procedure for performing the benzoin condensation of benzaldehyde, involving dissolving thiamine hydrochloride in water and ethanol, adding sodium hydroxide, then benzaldehyde and heating. The product is colorless crystals with a melting point of 134-135°C. Atom economy and percent yield are discussed as measures of a reaction's efficiency and effectiveness. Finally, the 12 principles of

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    Benzoin Condensation: - 1 - DE Jones

    Uploaded by

    Liz Hackett
    39 views9 pages
    The document describes the benzoin condensation reaction, which is the condensation of aldehydes in an oxidatively balanced process to form acyloins, compounds with a hydroxyl group bonded to a carbonyl group. It is an important reaction in biochemical processes like the pyruvate dehydrogenase reaction. The document also provides the experimental procedure for performing the benzoin condensation of benzaldehyde, involving dissolving thiamine hydrochloride in water and ethanol, adding sodium hydroxide, then benzaldehyde and heating. The product is colorless crystals with a melting point of 134-135°C. Atom economy and percent yield are discussed as measures of a reaction's efficiency and effectiveness. Finally, the 12 principles of

    Original Description:

    Acyloin Lecture organic

    Original Title

    Exp 7 Acyloin Lecture

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    The document describes the benzoin condensation reaction, which is the condensation of aldehydes in an oxidatively balanced process to form acyloins, compounds with a hydroxyl group bonded to a carbonyl group. It is an important reaction in biochemical processes like the pyruvate dehydrogenase reaction. The document also provides the experimental procedure for performing the benzoin condensation of benzaldehyde, involving dissolving thiamine hydrochloride in water and ethanol, adding sodium hydroxide, then benzaldehyde and heating. The product is colorless crystals with a melting point of 134-135°C. Atom economy and percent yield are discussed as measures of a reaction's efficiency and effectiveness. Finally, the 12 principles of

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    39 views9 pages

    Benzoin Condensation: - 1 - DE Jones

    Uploaded by

    Liz Hackett
    The document describes the benzoin condensation reaction, which is the condensation of aldehydes in an oxidatively balanced process to form acyloins, compounds with a hydroxyl group bonded to a carbonyl group. It is an important reaction in biochemical processes like the pyruvate dehydrogenase reaction. The document also provides the experimental procedure for performing the benzoin condensation of benzaldehyde, involving dissolving thiamine hydrochloride in water and ethanol, adding sodium hydroxide, then benzaldehyde and heating. The product is colorless crystals with a melting point of 134-135°C. Atom economy and percent yield are discussed as measures of a reaction's efficiency and effectiveness. Finally, the 12 principles of

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 9

    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.).

    DE Jones

    -1-

    Benzoin Condensation: Mechanism

    DE Jones

    -2-

    Experimental
    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

    DE Jones

    -3-

    Experimental
    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

    DE Jones

    -4-

    Experimental
    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

    DE Jones

    -5-

    Experimental
    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

    DE Jones

    -6-

    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


    DE Jones -7-

    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.

    DE Jones

    -8-

    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.

    DE Jones

    -9-

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