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    5 Aldol

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    Antinia Taylor-Dantes

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    5 Aldol

    Uploaded by

    Antinia Taylor-Dantes
    5 views4 pages

    Original Title

    5-Aldol

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    © © All Rights Reserved

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    5 views4 pages

    5 Aldol

    Uploaded by

    Antinia Taylor-Dantes

    Copyright:

    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    of 4

    Lab 5-Aldol Condensation

    Introduction:
    The α-proton of a carbonyl compound is more acidic than alkane C-H bonds (pKa range: ~9 to
    ~25 compared to ~50), and it can be deprotonated by a base to form an enolate. Enolates are
    nucleophilic and can react with electrophilic carbonyls like ketones or aldehydes to produce α,
    β-unsaturated carbonyl compounds. This type of reaction is called aldol condensation, which
    includes an aldol reaction and dehydration. Watch a video “aldol reaction”.
    In this lab, acetophenone will be treated with sodium hydroxide to form an enolate, which will
    react with benzaldehyde to generate chalcone as product. Chalcone has a conjugate system,
    which is responsible for its 350-400 nm absorption in UV-Vis spectrum. This absorption is
    responsible for the yellow color of chalcone.

    Procedure:
    1) Prepare an ice-water bath in a 100-ml beaker; then add 4 ml ethanol and 6 ml 30%
    NaOH to another 50-ml beaker. Then add a magnetic stir bar to the 50-ml beaker and
    put the beaker into the ice-water bath. Stir the solution for 5 minutes, then remove the
    ice-water bath and continue stirring.
    2) In a clean, dry, short test-tube, add 0.5 ml acetophenone and 0.5 ml benzaldehyde.
    Swirl, then use a pipet to slowly (dropwise) add the mixture into the stirring solution
    from the previous step; then stir the solution for one hour at room temperature.
    3) Add a piece of ice to the reaction and stir for 10 minutes, the ice should melt, and
    product should precipitate. Collect the solid product using vacuum filtration, spread the
    solid on a tared watch glass, put it in fume hood to air-dry for 30 minutes.
    4) Weigh the product and calculate the theoretical and percent yields. Measure the
    melting point of the dry product. The melting point of pure chalcone should be around
    55-57 °C.

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    Post lab questions
    1. What is the pKa range of the α-proton of a carbonyl compound?

    2. What is the color of the product chalcone, and what is responsible for this color?

    3. Based on the amount of two starting materials (0.5 ml acetophenone and 0.5 ml
    benzaldehyde), determine the limiting reactant and excess reactant.

    4. What is the theoretical yield in grams?

    5. What is the percent yield of your product?

    Page 4 of 4

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