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    E2_2 - Organic Synthesis (Preparation of Derivative).Doc

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    E2_2 - Organic Synthesis (Preparation of Derivative).Doc

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    E2_2 - Organic Synthesis (Preparation of Derivative).Doc

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    f20220889

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    © All Rights Reserved
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    Preparation (Synthesis) of Derivatives

    Aim:

    To prepare derivative and confirm the presence of functional group.

    Theory:

    To determine the actual identity and structure of an unknown compound there are different
    techniques. Modern x-ray and spectroscopic techniques have made the job much easier, but
    for some very complex molecules, identification and structure determination remain a
    challenge. In addition to spectroscopic information and information obtained from other
    instrumental methods, chemical reactions can provide useful structural information, and
    physical properties can contribute significantly to confirming the identity of a compound.

    A derivative is usually a solid material which can readily be prepared from an unknown (in
    this experiment aldehyde) and can be easily isolated and purified. Moreover, it should be
    crystalline and differ in physical properties from an unknown. Formation of derivative
    involves a reaction between the functional group and another reagent. The melting point of
    the derivative can be used as proof of the identity of the unknown.

    In this experiment we will be preparing derivative of aldehyde and we will validate the test to
    identify the functional group using the derivative.
    Tests for identification of aldehyde/ketones by forming derivative are:
     Iodoform reaction
     Schiff’s reagent
     2,4 dinitrophenylhydrazine reagent (Brady’s reagent)

    Both aldehydes and ketones react with 2,4- dinitrophenylhydrazine to form a solid 2,4-
    dinitrophenylhydrazone (DNP) derivative. The classification test serves also as derivative
    formation. The color of this derivative can also provide useful structural information. If the
    solid is yellow, this most often means that the carbonyl group in the unknown is
    unconjugated. A reddish-orange color most likely means that the carbonyl group is
    conjugated.
    Formation of 2,4-dinitrophenylhydrazone:

    There are exceptions to this though so care should be taken when interpreting this
    observation. In a few cases, compounds in which the carbonyl group is not conjugated
    produce orange precipitates. Note carefully that simply having a double bond or phenyl group
    somewhere in an aldehyde or ketone does not necessarily mean that the carbonyl group is
    conjugated. The double bond must be separated from the carbonyl by one single bond only. If
    the double bond is further away, it is isolated from the carbonyl and not conjugated with the
    carbonyl.
    Chemicals and Apparatus:
    100 ml flask, 2,4 Dinitrophenylhydrazine, Ethanol, Methanol, Concentrated HCl,
    Benzaldehyde, Water bath, Distilled water, Whatman filter paper, Funnel, Test tube and
    Spirit lamp

    Procedure:
    1. Weigh 0.1 g of 2,4 dinitrophenylhydrazine in the flask. To this add 10 ml of
    methanol.
    2. Add 5 drops of concentrated HCl and keep the solution in water bath for 10 minutes
    to make it warm. (Adjust Water bath temperature to 45° C). Then cool the solution to
    room temperature.
    3. Take another flask. Measure 1 ml methanol and to this add 1 drop of benzaldehyde.
    4. Transfer this solution to the first flask and warm the solution in water bath for 1-2
    minutes and then allow it to stand for 15 minutes at room temperature.
    5. During this incubation period, if the test is positive then the precipitate will form. If it
    doesn’t form precipitate then add cold water drop wise to the mixture (Do not add
    excess amount of water).
    6. Collect the product by vacuum filtration (When filtering aqueous solutions by suction
    filtration, use a gentle vacuum), wash with distilled water and air dry.
    7. The obtained product can be recrystallized from aqueous Ethanol. This can be done
    by dissolving the product into the ethanol and heating the mixture to boiling point of
    ethanol and the then filter.
    8. Cool the filtrate slowly at first and then in an ice bath, if necessary. The crystals
    should separate out this stage. Filter the mixture and air dry the formed derivative.

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