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14.9: Reactions of Epoxides with Grignard and Organolithium Reagents

  • Page ID
    183042
  • Grignard Reactions with Epoxides

    Grignard reactions with ethylene oxide produce a primary alcohol containing two more carbon atoms than the original Grignard reagent.

    Grig epoxide example.png

    The first step of the mechanism is shown below. With the second step following the protonation step common to the other reaction pathways studied in this section. This reaction follows the same SN2 mechanism as the opening of epoxide rings under basic conditions since Grignard reagents are both strong nucleophiles and strong bases.

    Grignard reagent with ethylene oxide to produce a primary alcohol

    Exercise

    12. Given the following, predict the product assuming only the epoxide is affected. (Remember stereochemistry)

    alt

    13. Predict the product of the following, similar to above but a different nucleophile is used and not in acidic conditions. (Remember stereochemistry)

    alt

    14. Epoxides are often very useful reagents to use in synthesis when the desired product is a single stereoisomer. If the following alkene were reacted with an oxyacid to form an epoxide, would the result be a enantiomerically pure? If not, what would it be?

    alt

    Answer

    12.

    altNote that the stereochemistry has been inverted

    13.

    alt

    14.

    First, look at the symmetry of the alkene. There is a mirror plane, shown here.

    alt Then, think about the mechanism of epoxidation with an oxyacid, take for example mCPBA. The mechanism is concerted, so the original cis stereochemistry is not changed. This leads to "two" epoxides.

    alt However, these two mirror images are actually identical due to the mirror plane of the cis geometry. It is a meso compound, so the final result is a single stereoisomer, but not a single enantiomer.

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