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  • CHEM F311 Lecture 37 Mannich Reaction and Use of Specific Enol Equivalents

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    The document summarizes lecture 37 of the organic chemistry course CHEM F311. It recaps carbonyl condensation reactions and previews the Mannich reaction and use of specific enol equivalents, including those with activating groups and Wittig and Reformatsky reagents. The Mannich reaction mechanism is shown adding formaldehyde, an amine, and HCl to a carbonyl. Examples of specific enol equivalents are given like esters with activating carbonyls and Wittig/Reformatsky reagents converting carbonyls to alkenes and alcohols.

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    The document summarizes lecture 37 of the organic chemistry course CHEM F311. It recaps carbonyl condensation reactions and previews the Mannich reaction and use of specific enol equivalents, including those with activating groups and Wittig and Reformatsky reagents. The Mannich reaction mechanism is shown adding formaldehyde, an amine, and HCl to a carbonyl. Examples of specific enol equivalents are given like esters with activating carbonyls and Wittig/Reformatsky reagents converting carbonyls to alkenes and alcohols.

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    21 views6 pages

    CHEM F311 Lecture 37 Mannich Reaction and Use of Specific Enol Equivalents

    Uploaded by

    living luxurious
    The document summarizes lecture 37 of the organic chemistry course CHEM F311. It recaps carbonyl condensation reactions and previews the Mannich reaction and use of specific enol equivalents, including those with activating groups and Wittig and Reformatsky reagents. The Mannich reaction mechanism is shown adding formaldehyde, an amine, and HCl to a carbonyl. Examples of specific enol equivalents are given like esters with activating carbonyls and Wittig/Reformatsky reagents converting carbonyls to alkenes and alcohols.

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    © All Rights Reserved
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    CHEM F311 Organic Chemistry – III

    Lecture 37 – 01st Dec. 2022


    Recap
     Control in carbonyl condensations
     Methods for controlling cross condensations

     Intramolecular reactions are easier to control

     Use of compounds which cannot enolise


    Preview
     Mannich reaction

     Use of specific enol equivalents


     Presence of activating groups
     Witting and Reformatsky reagents

     Enamines
    Mannich reaction

    O HCHO O

    NHR2 NR2
    HCl
    O

    O O
    HCl
    + HCHO + NH N

    OMe

    O
    O
    Use of Specific Enol Equivalents
    Presence of activating groups
    CO2Et

    CONH2

    NC

    piperidine Ph
    COOEt PhCHO + COOEt TM
    COOEt COOEt
    EtOOC COOEt
    Wittig & Reformatsky reagents
    COOEt
    O
    EtO
    P COOEt
    O EtO
    TM
    OH NaH

    CO2Et
    (i) Zn
    BrCH2COOEt TM
    OH
    (ii) Et2CO

    CO2H
    HO
    O HCHO O
    (i) MeI O O
    AcOH
    Et2NH, H+
    (ii) NaHCO3
    overnight
    NEt2 OAc

    BrZnCH2COOMe

    OH OH OH
    (i) KOH, H2O

    O O CO2H (ii) H+ COOMe


    HO OAc

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