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    Elimination Reactions Name Rxns

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    Hiba Rehman

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    Elimination Reactions Name Rxns

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    Hiba Rehman
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    0 views32 pages

    Elimination Reactions Name Rxns

    Uploaded by

    Hiba Rehman

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
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    Elimination reactions

    SN
    Predict the most likely mechanism and the
    product for the reaction below

    E2
    Which diastereomer of 1-bromo-4-t-butylcyclohexane, the cis
    or the trans, undergoes elimination more rapidly when treated
    with sodium ethoxide? Explain your answer.
    When 1-iodo-1-methylcyclohexane is treated with NaOEt as the base, the
    more highly substituted alkene product predominates. When t-BuOKis used
    as the base, the less highly substituted alkene predominates. Give the
    structures of the two products and offer an explanation.

    The small, unhindered base ethoxide yields the more stable alkene
    (Saytzeff’s product). When the bulky t-butoxide base is used, the most
    accessible hydrogen is removed. This results in the least highly
    substituted alkene (Hoffman’s product).
    Hofmann Elimination Reaction

    E2,thermal decomposition
    Slow

    200 TIMES FASTER


    Cope elimination, Thermal elimination

    Intramolecular 5-membered cyclic transition state, leading to a syn elimination

    Cope Reaction of N-oxides, which can easily be


    prepared in situ from tertiary amines with an
    oxidant such as peracid, leads to alkenes via a
    thermally induced syn-elimination in aprotic
    solvents.
    Chugaev elimination

    • Elimination of water from alcohols to produce


    alkenes. The intermediate is a xanthate
    Mechanism

    CH3I

    At about 200 °C, the alkene is formed by an intramolecular elimination. In a 6-


    membered cyclic transition state the hydrogen atom is removed from the carbon
    atom β to the xanthate oxygen in a syn-elimination. The side product decomposes
    to carbonyl sulfide (OCS) and methanethiol.
    Rigid geometry
    Grieco Elimination

    • Dehydration of an aliphatic primary alcohol


    through a selenide intermediate to deliver a
    terminal alkene.
    Corey–Winter olefin synthesis

    syn-elimination

    DMAP: 4-(Dimethylamino)pyridine
    Thiophosgene
    Mechanism
    Ramberg–Bäcklund reaction
    Mechanism
    Claisen Condensation

    • Carbon–carbon bond forming reaction that occurs


    between two esters or one ester and another carbonyl
    compound in the presence of a strong base. The
    reaction produces a β-keto ester or a β-diketone.
    • At least one of the reagents must be
    enolizable (have an α-proton and be able to
    undergo deprotonation to form the
    enolate anion).
    • The base used must not interfere with the
    reaction by undergoing nucleophilic
    substitution or addition with a carbonyl
    carbon.
    Mixed (or "crossed") Claisen condensation,
    where one enolizable ester or ketone and one
    non-enolizable ester are used.
    Dieckmann condensation

    • Intramolecular chemical reaction of


    diesters with base to give β-ketoesters.

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