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    Ochem 13

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    This experiment prepared benzilic acid through the rearrangement of benzil. Benzil was reacted with potassium hydroxide to produce benzilic acid. The product was analyzed and had a 52% yield, a melting point of 150°C which matched expectations, and an IR spectrum consistent with benzilic acid. Sources of error may have included impure glassware and some loss of product during transfer and filtration.

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    Ochem 13

    Uploaded by

    Izzy
    160 views2 pages
    This experiment prepared benzilic acid through the rearrangement of benzil. Benzil was reacted with potassium hydroxide to produce benzilic acid. The product was analyzed and had a 52% yield, a melting point of 150°C which matched expectations, and an IR spectrum consistent with benzilic acid. Sources of error may have included impure glassware and some loss of product during transfer and filtration.

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    This experiment prepared benzilic acid through the rearrangement of benzil. Benzil was reacted with potassium hydroxide to produce benzilic acid. The product was analyzed and had a 52% yield, a melting point of 150°C which matched expectations, and an IR spectrum consistent with benzilic acid. Sources of error may have included impure glassware and some loss of product during transfer and filtration.

    Copyright:

    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    160 views2 pages

    Ochem 13

    Uploaded by

    Izzy
    This experiment prepared benzilic acid through the rearrangement of benzil. Benzil was reacted with potassium hydroxide to produce benzilic acid. The product was analyzed and had a 52% yield, a melting point of 150°C which matched expectations, and an IR spectrum consistent with benzilic acid. Sources of error may have included impure glassware and some loss of product during transfer and filtration.

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    © All Rights Reserved
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    Elizabeth Ping | February 28, 2012| 1

    Preparation of Benzilic Acid

    Introduction:

    The purpose of this experiment was to prepare benzilic acid by the rearrangement of the alpha-
    diketone benzil as well as to determine the melting point and IR of benzilic acid

    Benzil to benzilic acid

    Mechanism of the rearrangement of benzil to make benzilic acid

    Procedure:
    See attachment.

    Observations:

    Dried product (Benzilic acid) 0.056 g


    Percent yield 52%
    Melting point Benzilic acid (expected: 150 °C) 150 °C

    See IR spectroscopy sheet for benzilic acid.


    Elizabeth Ping | February 28, 2012| 2

    Calculations:

    Theoretical yield:

    Benzil= (0.1 g)(1 mol/210.232 g) =4.757X10-4 mol Benzil

    KOH = (0.25 mL)(2.044g/1 mL)(1 mol/56.097 g)=9.111X10-3 mol KOH

    Therefore, Benzil is the limiting reagent.

    (4.757X10-4 mol Benzil)(1 mol Benzilic acid/1 mol Benzil)(228.247 g/mol Benzilic acid/1 mol
    Benzilic Acid)= 0.1086 g Benzilic acid

    Percent yield =(actual/theoretical)X 100%= (0.056 g /0.1086 g)*100= 52%

    Conclusion:

    In this experiment, benzilic acid was prepared by a rearrangement of the alpha-diketone benzil.
    The possible amount of benzilic acid was 0.1086 g; while 0.056 g was the actual amount
    produced which gave a percent yield of 52%. The observed melting point of benzilic acid was
    150 °C which is the same as the expected melting point of benzilic acid. This suggests that the
    product is pure. The IR of benzilic acid showed an O-H at ~3400 cm-1, carboxylic acid at ~2800
    cm-1 (very wide), C=O at ~1700 cm-1, C-O at ~1250 cm-1 and an aromatic at ~700 and 750 cm-1.

    Sources of error may have been due to using unclean glassware that may have produced side
    reactions. Some of the product may have been lost during transferring and during the filtration
    process since some green/pale brown color could be seen in the Erlenmeyer flask.

    Questions:

    See attachment.

    References:

    Pavia, Donald, Gary Lampman, George Kriz, and Randall Engel. Introduction to Organic
    Laboratory Techniques: A Microscale Approach. Belmont: Thomson Brooks, 2007.

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