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Alkenes as good nucleophiles

Discussion in 'MCAT Study Question Q&A' started by avenlea, 09.22.14.

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  1. avenlea

    avenlea 5+ Year Member

    Joined:
    03.29.11
    Messages:
    482
    Status:
    Pre-Medical
    Hi,

    I got a passage recently that had an alkene and a carbene and asked which was the electrophile and nucleophile. I was very confused by why the alkene would be considered to be the nucleophile and have more electron density when the carbene literally has a lone pair on it.

    Also confused why pi electrons and pi orbitals contribute to nucleophilicity in general.

    Thanks!
     
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  3. tdod

    tdod 2+ Year Member

    Joined:
    10.30.11
    Messages:
    209
    π orbitals contribute to nucleophilicty b/c the π orbitals are located above and below the plane of the sigma bond. Because the sigma bond is directly between two nuclei, the π bond is above and below the 2 nuclei (see google images). Consequently, the π electrons are less stabilized by the nuclei and therefore more nucleophilic.

    The carbene is electrophilic because it has an incomplete octet; in contrast, an alkene carbon has a complete octet.
     
    texan2414 likes this.

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