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    Aldol Condensation Reaction PDF

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    This document summarizes an experiment on aldol condensation reactions. The objectives were to synthesize dibenzalacetone and benzalacetophenone, measure their melting points, and understand the aldol reaction mechanism. Dibenzalacetone was successfully synthesized in part one, yielding 84% before recrystallization and 55% after. Its melting point was lower than expected, indicating impurities. Part two to make benzalacetophenone was unsuccessful due to a procedural error. Aldol condensation reactions join molecules with the loss of a small molecule like water, and an enolate ion acts as a nucleophile in the synthesis.

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    Aldol Condensation Reaction PDF

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    aizat
    342 views6 pages
    This document summarizes an experiment on aldol condensation reactions. The objectives were to synthesize dibenzalacetone and benzalacetophenone, measure their melting points, and understand the aldol reaction mechanism. Dibenzalacetone was successfully synthesized in part one, yielding 84% before recrystallization and 55% after. Its melting point was lower than expected, indicating impurities. Part two to make benzalacetophenone was unsuccessful due to a procedural error. Aldol condensation reactions join molecules with the loss of a small molecule like water, and an enolate ion acts as a nucleophile in the synthesis.

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    This document summarizes an experiment on aldol condensation reactions. The objectives were to synthesize dibenzalacetone and benzalacetophenone, measure their melting points, and understand the aldol reaction mechanism. Dibenzalacetone was successfully synthesized in part one, yielding 84% before recrystallization and 55% after. Its melting point was lower than expected, indicating impurities. Part two to make benzalacetophenone was unsuccessful due to a procedural error. Aldol condensation reactions join molecules with the loss of a small molecule like water, and an enolate ion acts as a nucleophile in the synthesis.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    342 views6 pages

    Aldol Condensation Reaction PDF

    Uploaded by

    aizat
    This document summarizes an experiment on aldol condensation reactions. The objectives were to synthesize dibenzalacetone and benzalacetophenone, measure their melting points, and understand the aldol reaction mechanism. Dibenzalacetone was successfully synthesized in part one, yielding 84% before recrystallization and 55% after. Its melting point was lower than expected, indicating impurities. Part two to make benzalacetophenone was unsuccessful due to a procedural error. Aldol condensation reactions join molecules with the loss of a small molecule like water, and an enolate ion acts as a nucleophile in the synthesis.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 6

    lOMoARcPSD|3377713

    Aldol condensation reaction

    Chemistry (Trinity College Dublin University of Dublin)

    StuDocu is not sponsored or endorsed by any college or university


    Downloaded by Aizat aziz (aizat.aziz1997@gmail.com)
    lOMoARcPSD|3377713

    Experiment 1

    Aldol Condensation reactions

    Introduction

    (a) Objectives
     To synthesize Dibenzalacetone.
     To synthesize Benzalacetophenone.
     To measure the melting point of the sample.
     To understand the mechanism of an Aldol Reaction.

    (b) Theory

    An Aldol condensation reaction is one in which an enol or an enolate ion reacts


    with a Carbonyl compound to form β-hydroxyaldehyde or a β-hydroxyketone,
    hence a dehydration gives a conjugate enone. In both parts of this practical
    experiment Benzaldehyde reacts with a ketone in the presence of a base to
    produce β-unsaturated ketones. The reaction that the experiments follow is an
    example of a crossed aldol condensation reaction where the intermediate in the
    reaction becomes dehydrated to produce the resonance- stabilised unsaturated
    ketone. The ketone loses a proton from an alpha-carbon to then form an enolate
    ion, which attacks the carbonyl carbon of the aldehyde to yield, after protonation
    alpha, beta-hydroxyketone. The intermediate formed for the aromatic aldehyde is
    unstable and is subjected to base-catalysed dehydration, until the unsaturated
    product is yielded. An important point to note is that a crossed-aldol condensation
    leads to a number of different products, unless one of the carbonyl compounds
    that is involved in the reaction cannot form an enolate ion (meaning compound
    has no alpha-hydrogens). An aromatic aldehyde, such as Benzaldehyde is
    sufficient for the reaction as only one enolate ion will form, which is from the other
    carbonyl compound. Hence formation, the nucleophilic enolate ion attacks the
    carbonyl carbon to form a β-hydroxycarbonyl product. The β-hydroxycarbonyl
    product then eliminates a molecule of water to form a conjugated system
    composed of a double bond and the carbonyl group. The elimination process with
    regards to part one of the experiment was particularly fast as the alkene is
    stabilised by conjugation to not only the carbonyl but also benzene. The
    theoretical melting point of Dibenzalacetone is 110-111 °C. In theory, the melting
    point of Dibenzalacetone is 55-57°C.

    Reaction Mechanisms:

    See post practical part (i) for reaction mechanisms

    Experiment procedure

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    lOMoARcPSD|3377713

    Part One – Synthesis of Dibenzalacetone.

    Benzaldehyde (2.88g; 2.77mL) was added to a conical flask with acetone (0.79g;
    1mL). The solution was shaken to ensure a homogeneous solution. Hence, 2M
    sodium hydroxide (40mL) and ethanol (30mL) was added to a beaker. Half of the
    solution from the conical flask was added to the beaker and mixed several times.
    After 15 minutes, the remainder of the solution was added to the beaker. Ethanol
    was used to ensure that all of the material had been transferred to the reaction
    vessel. The reaction was timed for 30 minutes and hence the product was collected
    by suction filtration. The solid that was collected was washed with water (3 x 60mL)
    and then sucked as dry as possible. The product was then weighed using a scales
    and the percentage yield before Recrystallisation was calculated. The
    Dibenzalacetone was then recrystallized from ethanol (2.5mL/g). The product was
    then dried in air and the percentage yield and melting point of the sample was
    determined.

    Part Two- Synthesis of Benzalacetophenone.

    Benzaldehyde (2.88g; 2.77mL) was added to a conical flask with acetophenone


    (3.26g; 3.17mL). The solution was mixed to ensure a homogeneous solution. Half of
    the mixture was added to a beaker containing 2M sodium hydroxide (40mL) and
    ethanol (30mL). The solution was swirled well and after 15 minutes the remainder of
    the benzaldehyde/acetone mixture was added. Ethanol was used to transfer all the
    solution to the reaction vessel. The solution was placed in ice. The reaction was
    timed for 30 minutes, swirled occasionally. The solid was recrystallized. The product
    was hence collected by suction filtration. Percentage yield and melting point was
    determined.

    Results

    Part One:

    Mr of acetone: 3(12.011)+ 6(1.0079) + 15.9994= 58.0798g.

    Theoretical yield: 0.79g/ 58.0798g= 0.01360197521 moles.

    Mr of Dibenzalacetone: 17(12.011)+ 14(1.0079) + 15.9994= 234.297g.

    Amount of Dibenzalacetone Crystals obtained: 2.69g.

    Actual yield: 2.69g/234.297g= 0.01148115426 moles.

    Percentage yield before Recrystallization: Act/Theoretical:


    0.01148115426/0.01360197521 x 100/1= 84.40799284%.

    Recrystallization:

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    lOMoARcPSD|3377713

    Crystals attained after Recrystallization: 2.69g- 1.47g= 1.22g.

    Actual yield: 1.47g/234.297g=0.006274088016moles.

    Theoretical Yield: 0.006274088016/0.01148115426 x 100/1= 54.64684015 is approx


    equal to a 55% yield.

    Melting point of Dibenzalacetone: 95 °C.

    Part Two:

    Mr of Benzaldehyde: 6(12.011) + 5(1.0079) + 12.011+ 1.0079+


    15.9994=106.1238g.

    Mr of Acetophenone: 8(12.011) + 8(1.0079) + 15.9994= 120.1506g.

    1 x 2.88g/ 106.1238g= 0.02713811605 moles.

    120.1506g x 0.02713811605= 3.260660926g

    X= amount of Acetophenone required= 3.260660926g.

    Density of Acetophenone= 1.03g/cm^3.

    Amount required = 3.165690219 approx 3.17mL.

    Discussion

    In part one of the experiment the yield dramatically dropped after recrystallization. It
    can be thought that this occurred for a number of reasons. One of which could
    perhaps be that not all of the crystals were washed with ethanol and then transferred
    into the filtration apparatus. Another could be that there was a number of impurities
    present before recrystallization and hence some of these impurities were removed
    after recrystallization. In addition, some of the product may have been lost due to
    evaporation. Finally, some of the product could also have been lost during the
    filtration process. The melting point was lower (95 °C) than the expected (110-111°C).
    The lower melting point resulted as there was impurities present and impurities tend
    to lower the melting point of compounds. In Part two of the experiment the limiting

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    lOMoARcPSD|3377713

    reagent was found and its molar value and hence its molar value was multiplied by
    the molecular mass of Acetophenone in order to calculate the value of x. The X
    value was the amount of Acetophenone that was required to synthesis
    Benzalacetophenone. The value of X was divided by the density of the ketone in
    order to calculate the value in mL. The percentage yield and melting point for Part
    Two was not calculated, due to the fact the experiment was not successful. The
    experiment was not successful, due to not following procedures efficiently enough.
    The mixture of Benzaldehyde and Acetophenone was added entirely to the NaOH
    and ethanol, instead of in two aliquots (the second being after 15 minutes). Due to
    not following the correct procedure Crystals did not form in the conical flask.
    Perhaps, heating would have helped the solution to speed up the formation of
    Crystals too.

    Conclusions

    Condensation reactions are reactions which join two or more molecules together,

    usually with the loss of a small molecule such as water or an alcohol. Precaution

    needs to be taken when following lab procedures, to ensure one obtains coherent

    results. An enolate ion acts effectively as a nucleophile, which can be used to

    synthesize Dibenzalacetone. Chalcone (Benzalacetophenone) is an important

    aromatic ketone and enone that forms the central core in many biological

    compounds.

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    lOMoARcPSD|3377713

    Downloaded by Aizat aziz (aizat.aziz1997@gmail.com)

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