CHEM12C Ch. 21 Aldehydes & Ketones

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daynuhmay
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CHEM12C Ch. 21 Aldehydes & Ketones
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2013-06-23 19:24:09
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Aldehydes Ketones
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Aldehydes & Ketones
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    • - The mechanism has two steps.
    • - H:– adds to the planar C=O from
    • both sides.
    • - The mechanism has two steps.
    • - R:– adds to the planar C=O from
    • both sides.
    • - The mechanism has two steps.
    • - –CN adds to the planar C=O from both
    • sides.
    • - The reaction forms a new C–C σ bond and a
    • new C–C π bond.
    • • Ph3P=O is formed as by-product.
    • - The reaction is fastest at pH 4–5.
    • - The intermediate carbinolamine is unstable, and loses H2O to form the C=N.
    • - The reaction is fastest at pH 4–5.
    • • The intermediate carbinolamine is unstable, and loses H2O to form the C=C.
    • The reaction is reversible. Equilibrium favors
    • the product only with less stable carbonyl
    • compounds (e.g., H2CO and Cl3CCHO).
    • • The reaction is catalyzed with either H+ or –OH.
    • - The reaction is reversible.
    • - The reaction is catalyzed with acid.
    • - Removal of H2O drives the equilibrium
    • to favor the products.
    • - Step [1] is best with CH3X and RCH2X since the reaction follows an SN2 mechanism.
    • - A strong base is needed for proton removal in Step [2].
    • This reaction is the reverse of cyanohydrin
    • formation.

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