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Alkylation of benzonitrile

  1. Dec 3, 2014 #1
    1. The problem statement, all variables and given/known data
    Draw the products formed when benzonitrile ( C6H5CN) is treated with each reagent
    D. CH3CH2CH2Cl, AlCl3
    E. CH3COCl, AlCl3

    2. Relevant equations

    CN is meta director because N pulls the electron density, leaving the carbon atom more positively charged, therefore leading to resonance structure that isn't stabled if ortho / para.
    3. The attempt at a solution

    Well I thought we could do the reaction for D if we rearranged the alkyl halide to put the carbocation on a ( at least) 2ndare carbon.

    for E im not too sure why the reaction doesn't occur :/
     
  2. jcsd
  3. Dec 8, 2014 #2
    Thanks for the post! This is an automated courtesy bump. Sorry you aren't generating responses at the moment. Do you have any further information, come to any new conclusions or is it possible to reword the post?
     
  4. Dec 11, 2014 #3
    You're correct for the first one, although I was taught that Friedel-Crafts alkylations are unreactive to deactivated benzenes, as well as poorly reactive to an alkyl chain longer than 2 carbons.

    For the second one, Friedel-Crafts acylations are nonreactive to deactivated benzenes.
     
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