acid hydrolysis mechanism of acetals


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PDF GENERAL ACID CATALYSIS IF ACETAL HYDROLYSIS

The hydrolysis rates measured in buffer solutions of the twelve acetals sin died were found to be dependent on the concentration of undissooiated acid and

  • What is the mechanism of acetal hydration?

    The mechanism for acetal formation is similar to the formation of a hydrate.
    The mechanism for acetal formation can be divided into two parts, the first of which is addition of one equivalent of alcohol to form the hemiacetal.
    The second part of the mechanism involves conversion of the hemiacetal into the acetal.

  • In the first step, one of the oxygens will be protonated (either is possible).
    The other oxygen "kicks out" the one activated in the first step.
    So far so good.
    However, in the next step, water will attack the "carbonyl" carbon to give a hemi-acetal and a hydroxyl group.

  • What is the reaction mechanism for acetal?

    Acetal Formation Mechanism
    Formation of an acetal occurs when the hydroxyl group of a hemiacetal becomes protonated and is lost as water.
    The carbocation that is produced is then rapidly attacked by a molecule of alcohol.
    Loss of the proton from the attached alcohol gives the acetal.

  • In free solution, the acid-catalyzed hydrolysis of acetals generally proceeds through an A-1 mechanism in which the substrate is in fast pre-equilibrium with its protonated analogue and decomposition of the latter species is rate-limiting.
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