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Chemistry LibreTexts

MI5. Alkene Binding and Insertion

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  • Figure MI5.4. Hydride transfer to a bound alkene, drawn in the more common way.
    • The reverse of elimination is insertion.
    • A coordinated alkene is sometimes considered electrophilic because it is giving electrons to the metal.
    • A coordinated alkene is activated, like a coordinated carbonyl compound.

    Problem MI5.2.

    Draw the insertion products in the following cases.

    Problem MI5.3.

    Alkenes can be converted into other compounds through the use of organometallic reagents, such as "Schwartz's reagent" (below). In this case, the resulting alkyl compound can easily be converted into a long-chain alkyl halide or alcohol through the addition of appropriate reagents. Provide a mechanism for the reaction shown below.

    Problem MI5.4.

    1,2-alkyl insertions and -eliminations are also known in a few cases, although they are much slower than 1,2-hydride insertions and -eliminations. Show the 1,2-insertion products for the following cases.