Arrange the following reactions according to their probability of happening spontaneously in the aspirin molecule, in a neutral medium under normal temperature and pressure conditions. Start with 1 for the reaction with the lowest probability up to 5 for the reaction with the highest probability:

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A ❏ hydrolysis of ethanoate group

B ❏ partial reduction of the aromatic ring

C ❏ oxidation of the aromatic ring

D ❏ racemisation

E ❏ formation of intramolecular H-bonding

8 COMMENTS

  1. The answer is below and Temitope David is the winner.
    Details below:
    The chemical structure of aspirin (acetylsalicylic acid) consists of an aromatic
    ring, a carboxyl moiety and a phenolic hydroxide esterified with acetic acid.
    Racemization of aspirin is impossible because it requires a chiral molecule.
    Aspirin does not have an asymmetric carbon atom and therefore is not a chiral
    molecule. The aromatic ring is very stable and hence it is not very reactive.
    Its total or partial reduction can occur by hydrogenation only in the presence
    of the appropriate catalysts and under high pressure. The oxidization of the
    aromatic ring is very difficult but, under certain conditions (for example, in the
    presence of free oxygen radicals), such a reaction can occur under mild
    conditions as, for example, when aspirin is used therapeutically and interacts
    within the arachidonic acid cascade in vivo. If aspirin is kept in a damp place,
    partial hydrolysis of the molecule may occur even at room temperature.
    Intramolecular hydrogen bonding is easily formed in aspirin. The planar
    structure of the acetylsalicylic acid molecule allows interaction between the
    hydrogen atom of the carboxyl group and the phenolic oxygen of the ester
    group. The resulting six-cyclic structure, which forms without energy, is quite
    stable.
    A ❏ 4
    B ❏ 2
    C ❏ 3
    D ❏ 1
    E ❏ 5

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