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    Final Examination: Take Home Question

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    Augustin Toma
    1) FeCl3 produces lower yields than AlCl3 in Friedel-Crafts reactions due to an unknown side reaction. Trace amounts of titanium in AlCl3 make it more reactive. 2) FeCl3 is less effective than AlCl3 for reactions using primary alkyl halides. AlCl3 forms a superacid that stabilizes carbocation intermediates better than FeCl3. 3) AlCl3 also allows for more selective alkylations through complex formation with nitroalkanes, giving it greater utility in Friedel-Crafts reactions.

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    Final Examination: Take Home Question

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    Augustin Toma
    51 views2 pages
    1) FeCl3 produces lower yields than AlCl3 in Friedel-Crafts reactions due to an unknown side reaction. Trace amounts of titanium in AlCl3 make it more reactive. 2) FeCl3 is less effective than AlCl3 for reactions using primary alkyl halides. AlCl3 forms a superacid that stabilizes carbocation intermediates better than FeCl3. 3) AlCl3 also allows for more selective alkylations through complex formation with nitroalkanes, giving it greater utility in Friedel-Crafts reactions.

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    1) FeCl3 produces lower yields than AlCl3 in Friedel-Crafts reactions due to an unknown side reaction. Trace amounts of titanium in AlCl3 make it more reactive. 2) FeCl3 is less effective than AlCl3 for reactions using primary alkyl halides. AlCl3 forms a superacid that stabilizes carbocation intermediates better than FeCl3. 3) AlCl3 also allows for more selective alkylations through complex formation with nitroalkanes, giving it greater utility in Friedel-Crafts reactions.

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    © All Rights Reserved
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    51 views2 pages

    Final Examination: Take Home Question

    Uploaded by

    Augustin Toma
    1) FeCl3 produces lower yields than AlCl3 in Friedel-Crafts reactions due to an unknown side reaction. Trace amounts of titanium in AlCl3 make it more reactive. 2) FeCl3 is less effective than AlCl3 for reactions using primary alkyl halides. AlCl3 forms a superacid that stabilizes carbocation intermediates better than FeCl3. 3) AlCl3 also allows for more selective alkylations through complex formation with nitroalkanes, giving it greater utility in Friedel-Crafts reactions.

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    Augustin Toma : 250668801

    Sunday, April 13, 2014

    Final Examination: Take Home Question


    FeCl3 has consistently been reported to produce lower yields when used as a
    substitute for AlCl3 in Friedel Craft alkylations/acylations. According to W.A Riddel and
    C.R. Noller, The ferric chloride has a detrimental action which is apparently due to the
    acceleration or inauguration of an unknown side reaction(Riddle,1930). Its postulated
    that the trace presence of Titanium in aluminum chloride lends itself to its greater
    reactivity

    (Gore,

    1955).

    Although

    FeCl3

    can

    be

    used

    in

    Friedel

    craft

    alkylations/acylations, it is notably less effective when used with primary alkyl halides,
    which are the least reactive alkylating agents(Olah,1995). The HCl-AlCl3 system, which is
    used in Friedel craft alkylations, is a super acid (unlike FeCl3), which is capable of giving
    greater stability to the intermediate carbocations (Olah, 2009). This is a consequence of
    the stronger attraction that the halogen of the alkyl halide will have to the aluminum
    chloride, this causes the alkyl group to become especially electrophilic. The more stable
    the intermediate, the more successful the reaction will be. In addition to this, aluminum
    chloride also forms complexes with nitro alkanes that can be used to perform more
    selective alkylation, giving it more utility in Friedel craft alkylations (Olah,1995).
    References
    Olah, George A., and George A. Olah. Superacid Chemistry. Hoboken, NJ: Wiley, 2009.
    Print.
    Riddell, W. A., and C. R. Noller. "Mixed Catalysts In The Friedel And Crafts Reaction. The
    Yield Of Benzophenone From Benzoyl Chloride And Benzene Using Ferric Chloride
    Aluminum Chloride Mixtures As Catalysts." Journal of the American Chemical Society
    52.11 (1930): 4365-369. Print.
    Gore, P. H. "The Friedel-Crafts acylation reaction and its application to polycyclic aromatic
    hydrocarbons." Chemical Reviews 55.2 (1955): 229-281.
    Olah, George A., and rpd Molnr. Hydrocarbon Chemistry. New York: Wiley, 1995.
    Print.

    Augustin Toma : 250668801

    Sunday, April 13, 2014

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