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    The Chemistry of Benzene-8

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    TiffannieNguyen
    This document discusses retrosynthetic analysis for organic synthesis. It emphasizes working backwards from the target product through precursor molecules in single steps to arrive at the starting material. Retrosynthetic analysis is presented as the best way to design multi-step syntheses, though it does not come naturally and requires practice. A trivial example is then given to illustrate the process, showing different reaction pathways and the need to separate ortho and para isomers.

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    The Chemistry of Benzene-8

    Uploaded by

    TiffannieNguyen
    9 views1 page
    This document discusses retrosynthetic analysis for organic synthesis. It emphasizes working backwards from the target product through precursor molecules in single steps to arrive at the starting material. Retrosynthetic analysis is presented as the best way to design multi-step syntheses, though it does not come naturally and requires practice. A trivial example is then given to illustrate the process, showing different reaction pathways and the need to separate ortho and para isomers.

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    or3ganicsyntyes flw hart

    Original Title

    Org Synth-1(1-2015)

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    This document discusses retrosynthetic analysis for organic synthesis. It emphasizes working backwards from the target product through precursor molecules in single steps to arrive at the starting material. Retrosynthetic analysis is presented as the best way to design multi-step syntheses, though it does not come naturally and requires practice. A trivial example is then given to illustrate the process, showing different reaction pathways and the need to separate ortho and para isomers.

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    Flag for inappropriate content
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    9 views1 page

    The Chemistry of Benzene-8

    Uploaded by

    TiffannieNguyen
    This document discusses retrosynthetic analysis for organic synthesis. It emphasizes working backwards from the target product through precursor molecules in single steps to arrive at the starting material. Retrosynthetic analysis is presented as the best way to design multi-step syntheses, though it does not come naturally and requires practice. A trivial example is then given to illustrate the process, showing different reaction pathways and the need to separate ortho and para isomers.

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    The Chemistry of Benzene-8

    The Name of the Game: Organic Synthesis

    108B
    Org Syn1

    With the chemistry of benzene now at your disposal, you can synthesize a truly remarkable
    variety of biologically and medicinally important molecules...I said MEDICINAL, you naughty
    boys and girls!!
    Remember: RETROSYNTHETIC ANALYSIS!! Work backwards one step at a time from
    the product to a molecule that, in one step, will give the product. The precursor molecule now
    becomes the product and the process is repeated until the starting material specified in the
    problem is reached.
    Retrosynthetic analysis is the best way to develop or analyze any proposed synthetic
    pathway. Ideally, you will learn to recognize the immediate precursors for each intermediate
    product along a given reaction pathway. Developing such recognition does, however, take lots of
    practice. Unless you are genetically predestined to be a politician, a lawyer, or a bureaucrat,
    working backwards does not come naturally. Trust me, kids: it's the only way to design a multistep synthesis.

    A Trivial But Illuminating Example


    Br
    FeBr3/Br2

    FeBr3/Br2

    KMnO4

    Cleanly gives
    bromobenzene

    CH3Cl,
    AlCl3

    COOH

    COOH

    Leads to toluene
    and other crappola;
    separate o,p and pray
    that Gary is in a good mood
    when he grades your exam...

    Gives meta!!
    Not a precursor

    Br

    CH3Cl,
    AlCl3

    (chocolate; espresso...)

    Br
    (sep o,p)
    So far, so good!

    FeBr3/Br2

    Gives o- and p-bromotoluene; must


    be separated, so you get to chant
    sep o, p; polyalkylation
    is also a problem
    Gives o- and p-bromotoluene;
    must be separated

    The magic words: separate o,p (!): an incantation of almost mythical proportions come exam
    time. Since the physical properties (mp, bp, solubility) of the ortho, meta, and para isomers of a
    given compound are always significantly different, you can, in fact (or theory), physically
    separate them which means that you can invoke this incantation of near mystical ecstatic power
    while taking an O-Chem exam to get yourself out of the synthetic mess that your refusal to work
    backwards has just created for you...

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