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    Naeem Assignment

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    Tayyab Awan
    The document discusses retrosynthesis and stereoselectivity in organic synthesis. It defines retrosynthesis as a technique to plan a synthesis by reducing a target molecule into simpler structures through known reactions until commercially available starting materials are identified. Syntheses can be linear or convergent. Convergent synthesis is more efficient as it synthesizes fragments independently before combining them. The document provides examples of synthesizing different functional groups like alkenes through dehydration, Grignard reactions, eliminations, and using phosphonium ylides.

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    Naeem Assignment

    Uploaded by

    Tayyab Awan
    45 views13 pages
    The document discusses retrosynthesis and stereoselectivity in organic synthesis. It defines retrosynthesis as a technique to plan a synthesis by reducing a target molecule into simpler structures through known reactions until commercially available starting materials are identified. Syntheses can be linear or convergent. Convergent synthesis is more efficient as it synthesizes fragments independently before combining them. The document provides examples of synthesizing different functional groups like alkenes through dehydration, Grignard reactions, eliminations, and using phosphonium ylides.

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    The document discusses retrosynthesis and stereoselectivity in organic synthesis. It defines retrosynthesis as a technique to plan a synthesis by reducing a target molecule into simpler structures through known reactions until commercially available starting materials are identified. Syntheses can be linear or convergent. Convergent synthesis is more efficient as it synthesizes fragments independently before combining them. The document provides examples of synthesizing different functional groups like alkenes through dehydration, Grignard reactions, eliminations, and using phosphonium ylides.

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    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    45 views13 pages

    Naeem Assignment

    Uploaded by

    Tayyab Awan
    The document discusses retrosynthesis and stereoselectivity in organic synthesis. It defines retrosynthesis as a technique to plan a synthesis by reducing a target molecule into simpler structures through known reactions until commercially available starting materials are identified. Syntheses can be linear or convergent. Convergent synthesis is more efficient as it synthesizes fragments independently before combining them. The document provides examples of synthesizing different functional groups like alkenes through dehydration, Grignard reactions, eliminations, and using phosphonium ylides.

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    of 13

    Assignment OF

    RETROSYNTHESIS

    Topic: Stereoselectivity In Retrosynthesis of Organic Compounds


    Submitted By: M. Naeem
    Submitted To: Ma’am Ambreen Ghani
    Class: Bs Chemistry
    Semester : 8th
    Roll no. BSF1603449

    Date: 28-05-2020

    University of Education Lahore, Vehari Campus


    Definition

     Retrosynthetic analysis (retrosynthesis) is a technique for planning a


    synthesis, especially of complex organic molecules, whereby the complex
    target molecule (TM) is reduced into a sequence of progressively simpler
    structures along a pathway which ultimately leads to the identification of a
    simple or commercially available starting material (SM) from which a
    chemical synthesis can then be developed.
     Retrosynthetic analysis is based on known reactions (e.g the Wittig reaction,
    oxidation, reduction etc).
     The synthetic plan generated from the retrosynthetic analysis will be the
    roadmap to guide the synthesis of the target molecule
    Synthetic Planning

     Synthesis is a construction process that involves converting simple or


    commercially available molecules into complex molecules using specific
    reagents associated with known reactions in the retrosynthetic scheme.
     Synthesis can be grouped into two broad categories:
    (i) Linear synthesis
    (ii) Convergent synthesis
    Linear Synthesis

     In linear synthesis, the target molecule is synthesized through a series of


    linear transformations.
     Since the overall yield of the synthesis is based on the single longest route to
    the target molecule, by being long, a linear synthesis suffers a lower overall
    yield.
     The linear synthesis is fraught with failure for its lack of flexibility leading to
    potential large losses in the material already invested in the synthesis at the
    time of failure
    Convergent Synthesis

     In convergent synthesis, key fragments of the target molecule are synthesized


    separately or independently and then brought together at a later stage in the
    synthesis to make the target molecule.
     A convergent synthesis is shorter and more efficient than a linear synthesis
    leading to a higher overall yield. It is flexible and easier to execute due to the
    independent synthesis of the fragments of the target molecule
    One Functional Group

     One Functional Group Analysis Synthesis (path a)


    Disconnection close to the functional group
    (path a) leads to substrates (SE) that are readily
    available. Moreover, reconnecting these
    reagents leads directly to the desired TM in high
    yield using well-known methodologies.
    Disconnection via path b also leads to readily
    Analysis
    accessible substrates. However, their
    reconnection to furnish the TM requires more
    steps and involves two critical reaction
    attributes: quantitative formation of the
    enolate ion and control of its monoalkylation by
    ethyl bromide.
    Alkene Synthesis

     Alkenes can be made by the dehydration of alcohols 2, usually under acidic


    conditions.
     This route is particularly good for cyclic alkenes 3
     The same alkene is formed from 2 regardless of which side eliminates but 4
    gives a 76% yield of an 80:20 mixture of 5and 6
     When Zimmermann and Keck wished to study the photochemistry of a series
    of alkenes of the general structure 7
     They used the Grignard method and dehydrated 8 with POCI3 in pyridine
     Eliminations on alkyl halides done by the E2 mechanism with a strong
    hindered base to avoid SN2 reactions.
     This approach is good for terminal alkenes 10 as the elimination is successful
    on primary halides
     Triphenyl phosphine, reacts with an alkyl halide in an SN2 reaction to give a phos-
    phonium salt 18. Treatment with base, gives the phosphoniumylid 19.

     The carbanion end of the ylid adds to the aldehyde 22 and the 'betaine' then cyclises 23 to
    the four-membered ring which frag- ments to give the products 24. So the Z-alkene 20 is
    formed from the cis oxaphosphetane 24

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