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    16 Acetoacetic Malonic Esters ENG

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    georgia
    This document discusses several organic reactions including the Claisen condensation, Dieckmann reaction, acetoacetic ester synthesis, malonic ester synthesis, and Michael addition. It provides background on the reactions, including their applications and mechanisms. It also discusses the synthesis of barbiturates and introduces Rainer Claisen, Walter Dieckmann, Arthur Michael, and Emil Knoevenagel who made contributions to these reactions.

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    16 Acetoacetic Malonic Esters ENG

    Uploaded by

    georgia
    44 views10 pages
    This document discusses several organic reactions including the Claisen condensation, Dieckmann reaction, acetoacetic ester synthesis, malonic ester synthesis, and Michael addition. It provides background on the reactions, including their applications and mechanisms. It also discusses the synthesis of barbiturates and introduces Rainer Claisen, Walter Dieckmann, Arthur Michael, and Emil Knoevenagel who made contributions to these reactions.

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    This document discusses several organic reactions including the Claisen condensation, Dieckmann reaction, acetoacetic ester synthesis, malonic ester synthesis, and Michael addition. It provides background on the reactions, including their applications and mechanisms. It also discusses the synthesis of barbiturates and introduces Rainer Claisen, Walter Dieckmann, Arthur Michael, and Emil Knoevenagel who made contributions to these reactions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    44 views10 pages

    16 Acetoacetic Malonic Esters ENG

    Uploaded by

    georgia
    This document discusses several organic reactions including the Claisen condensation, Dieckmann reaction, acetoacetic ester synthesis, malonic ester synthesis, and Michael addition. It provides background on the reactions, including their applications and mechanisms. It also discusses the synthesis of barbiturates and introduces Rainer Claisen, Walter Dieckmann, Arthur Michael, and Emil Knoevenagel who made contributions to these reactions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 10

    11-Feb-19

    Acetoacetic and malonic esters.

    • Preparation. Claisen condensation.


    • Application of the acetoacetic and
    malonic ester into the organic
    synthesis.
    • Knoevenagel reaction.
    • Michael reaction.

    b-Dicarbonyl compounds

    1
    11-Feb-19

    Stabilization of the anion by electron delocalization involving both


    carbonyl groups

    The Claisen Condensation

    2
    11-Feb-19

    The Claisen Condensation

    Rainer Ludwig Claisen


    1851-1930

    Intramolecular Claisen Condensation


    The Dieckmann Reaction

    Walter Dieckmann
    1869 - 1925

    3
    11-Feb-19

    The Dieckmann Reaction

    PROBLEM: Write the structure of the Dieckmann cyclization product formed on treatment of
    each of the following diesters with sodium ethoxide, followed by acidification.

    Mixed Claisen Condensation

    Possible when one of the ester components is incapable of forming an enolate.

    4
    11-Feb-19

    The Acetoacetic Ester Synthesis

    The anion produced by proton abstraction from ethyl acetoacetate is nucleophilic.

    The new carbon–carbon bond is formed by an SN2-type reaction.

    Saponification and decarboxylation of the alkylated derivative of ethyl acetoacetate yields a


    ketone.

    The Acetoacetic Ester Synthesis

    The acetoacetic ester synthesis brings about the overall transformation of an alkyl halide to
    an alkyl derivative of acetone.

    5
    11-Feb-19

    Problem: Synthesise!

    The Malonic Ester


    Preparation

    6
    11-Feb-19

    The Malonic Ester Synthesis

    The malonic ester synthesis is conceptually analogous to


    the acetoacetic ester synthesis.

    The Malonic Ester Synthesis

    By performing two successive alkylation steps, the malonic ester synthesis can be
    applied to the synthesis of a,a-disubstituted derivatives of acetic acid:

    7
    11-Feb-19

    The Malonic Ester Synthesis


    It can be adapted to the preparation of cycloalkanecarboxylic acids
    from dihaloalkanes.

    Barbiturates

    8
    11-Feb-19

    Barbiturates

    Barbiturates
    Synthesis of Phenobarbital:

    9
    11-Feb-19

    Michael Addition

    Arthur Michael
    1853 - 1942

    Knoevenagel Condensation

    Emil Knoevenagel
    1865 - 1921

    Thank you for your attention!

    10

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