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    Proto Org Chem

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    Upendra Kkr
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    Proto Org Chem

    Uploaded by

    Upendra Kkr
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    protocol

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    Proto Org chem

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    4 views5 pages

    Proto Org Chem

    Uploaded by

    Upendra Kkr
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    © All Rights Reserved
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    of 5

    Task:-

    Preparation of dibenzalacetone from the reaction of acetone and benzaldehyde, under


    catalytic influence of sodium hydroxide solution. The final product is purified afterwards
    using recrystalization method.

    Method:-
    The experimental procedure is carried out according to the script, except as noted as follows.
    The precipitate of step-4 was, after washing with water, accidentally filled into the 250mL
    flask used in step-6 without measuring the pH beforehand. The precipitate was then removed
    and rinsed from the flask, and the filtration procedure was repeated until pH-7.0 was achieved
    In step 6, the precipitate was accidentally filled into a ceramic porcelain dish which had not
    been weighted. The precipitate was removed and filled into another porcelain dish .
    Additional notes and detailed descriptions of processed mentioned in the script:
    For cooling during steps 2-4, a water bath is used. The recrystallization apparatus of step-6
    was completed by a heating apparatus.

    Results:-
    Observations: 6-7 runs of washing were needed to reach pH-7.0 in step 5-. After three runs of
    washing with ice-cold 2-propanol was done in step-6.

    Reaction mechanism: –
    1) Theoretical basics:- Aldol reaction involves Aldehyde ie. Benzaldehyde and ketone ie
    acetone that has an α-hydrogen atom. Abstruction of an α-hydrogen base produces Carbanion
    which attacks the carbonyl carbon of the molecule by base initiated Nucleophillic addition
    reaction. An alcohol group is formed . After the alcohol dehydrates to form final the product.

    A nucleophile is an electron rich species which is negatively charged.An electrophile is an


    electron deficient species which has a positive charge on it. The reaction between
    benzaldehyde and acetone occurs in the presence of sodium hydroxide as a base. It is a type of
    mixed aldol condensation reaction.

    General reaction:-

    2 Benzaldehyde Acetone Dibenzalacetone Water


    Mole.Wt=106,13 g/mol Mole.Wt= 58,08 g/mol Mole.Wt=234,30 g/mol Mole.Wt=18 g/mol
    Mechanism:-

    Step-1- Deprotonation:-

    Acid-Base reaction Nucleophile Carbanion ion Enolate ion

    Resonance form of Enolate

    Acetone has α-hydrogen atom on both sides and this can be protonated to giverise a
    Nucleophile (resonance stabilized) enolate anion. Enolate is a an electron rich and highly
    reactive toward electrophile.

    Step-2 Nucleophilic attack:-

    Nucleophile(carbanion) Electrophile Alkoxide ion

    Benzaldehyde carbonyl carbon atom is more electrophilic than that of Acetone due to the
    partial positive charge on the carbon atom.

    Step-3 Protonation:-

    Acid-Base reaction and reformation of catalyst (OH -) β-hydroxy ketone


    The formation of alkoxide or phenoxide undergone protonation, giving a neutral β-hydroxy
    ketone having both alcohol (-OH) and (–C=O) carbonyl group. which undergoes base
    catalyzed dehydration reaction.

    Step-4 Deprotonation of α-carbon:-

    Second deprotonation with Sodium hydroxide leads to the formation of resonance stabilized
    carbanion.

    Step-5 Condensation and Elimination:-

    Dibenzalacetone

    Repetation of step -1 to step-2 will lead to synthesis of Dibenzalacetone.

    Elimination of hydroxide ion to form then α-β-unsaturated ketone called Benzalacetone. The
    entire sequential reaction is repeated to lead to condensation of Benzaldehyde gives the
    second α-carbonyl carbon of acetone collectively form Dibenzalacetone.
    Melting point of the yielded product:-

    Melting point range :- 113,5 °C-114,1 °C Literature value= 111° C-113°C

    Calculation of the theoretical yield:-

    C6 H5-CHO=10,6 gms, (CH3)2-CO = 2,9 gms

    =234,3 gm/ mol / 58,08 gm/mol x 2,9 gm


    =11,6988 gm=11,7 gm

    Experimental yield= 8,8 gms


    yield = 8,8 gm/11,7gm x 100% Literature value= 68,3%
    =75.21%

    Error Discussion:-
    The experiment yielded 75.2% of the theoretical amount of dibenzalacetone that could be
    attained. Literature however states a much lower experimental yield of around 42.7% for
    microscale and 68.3% for macroscale [4]. This could partly be because of the differences in
    procedure – firstly, no excess of benzaldehyde is used. The reactor is not cooled and allowed
    to cool for half an hour only. For washing, no ice-cold isopropanol is used, but ethanol.
    Likewise for recrystallization, the substance of choice is ethanol according to source
    [4].Nonetheless, the yield obtained in practical class could have been higher, due to the errors
    made during the experiment and remaining uncertainties: As a random error:
    The precipitate of step-4 was, after washing with water, accidentally filled into the 250mL
    flask used in step 6 without measuring the pH beforehand. The precipitate was then removed
    and rinsed from the flask, and the filtration was repeated until pH-7,0 was reached. In step-6,
    the precipitate was accidentally filled into a ceramic crucible which had not been weighted.
    The precipitate was removed and filled into another pan.

    Systematic errors may have occurred in the weighting of the substances, due to the balance
    used to determine the experimental yield having an accuracy of +/- 0.05g only.

    The melting point of the yielded substance is 113.5 °C – 114.1 °C.Literature gives a value of
    100.5-112 °C, while the script gives 111°C-113°C, suggesting significant impurity in the
    yielded substance. However, both systematic errors (accuracy of the melting point analyzing
    device +/- 0.05°C) and random errors may have occurred during the measurement of melting
    point. Remaining amount of different substances in the apparatus and different geometric
    isomers of dibenzalacetone also have to be taken into account.
    Answer to Additional questions

    a) What chemical structure is required for a compound to be coloured (to absorb in the visible
    region of light)?

    To absorb visible light, a compound needs a chromophore, a carrier of color. These


    chromophores contain electrons which are easy to put into an excited state and by that, absorb
    energy. [1] In case of dibenzalacetone, as an aromatic ketone, these would be electrons of
    three conjugated double bonds and delocalized electrons of two benzene rings.

    b) Which spectroscopic method is used to investigate coloured compound?formulate the


    Beer-Lambert equation?
    UV/VIS Spectroscopy can be used to analyze the properties of a compound in terms of
    absorption and reflection of visible or near-visible light. [2]The Lambert-Beer equation can be
    used to determine the extinction (E) of a material by giving thickness (d [m]), using the
    concentration oft his material in solution (c [Mol/L]) and the molar absorptivity ( [m2/Mol])
    which is a material constant. [2,3]

    Alternatively, E can be calculated from the intensity of the light used in the spectrometer (I0
    [W/m2]) and the light that has passed the specimen (I [W/m2]). [2]

    E=lg(I0/I) =c x d x 

    c) Which theoretical process (MO-theory) describes visible absorption?

    Molecular orbital theory describes the traits of various compounds with overlapping atomic
    orbitals, forming molecular orbitals. An example would be the orbital formed by a benzene
    ring, in which p-orbitals of six carbon atoms combine to form a large orbital above and below
    the plane oft he benzene ring and in which electrons can freely move (therefore called
    delocalized -electrons). -electrons are easy to put into an excited state in terms of energy,
    such as electromagnetic radiation, because the nuclei exert little influence on them. Since
    visible light is electromagnetic radiation of relatively little energy (Wavelength of 380-780
    nm), systems containing many delocalized -electrons can absorb visible light. When an
    electron returns to its ground state however, energy is released in the form of electromagnetic
    radiation. A compound reflects light of the color complementary to the color it absorbs. Since
    Dibenzalacetone appears yellow, it absorbs light of wavelengths of about 400nm (blue-
    violet). [1

    References
    1.C.E. Mortimer, U. Müller (2010): Chemie (10th edition), pp. 616-619; 61; 63-65
    2.Alan Cooper : Biophysical Chemistry (2004) pp-24-28-40,
    3.A. Teck, S. Grond et al. (2005) Chemie für Mediziner (6th edition) pp. 488, 489
    4.K.Williamson Macroscale and Microscale Organic Experiments(4th Edition)pp-454-456.
    5.Script for the practical Organic Chemistry. (SS2013) Hochschule Bonn-Rhein-Sieg.

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