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    Preparation of Carboxylic Acid and Their Derivatives

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    Yuni Purnamasari

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    Preparation of Carboxylic Acid and Their Derivatives

    Uploaded by

    Yuni Purnamasari
    11 views7 pages

    Original Title

    KARBOKSIL

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    11 views7 pages

    Preparation of Carboxylic Acid and Their Derivatives

    Uploaded by

    Yuni Purnamasari

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    of 7

    PREPARATION OF CARBOXYLIC

    ACID AND THEIR DERIVATIVES


    A. PREPARATION OF CARBOXYLIC ACIDS
    1. By oxidation of alkenes
    O O
    1. KMnO4, OH-, heat
    R C C R' R C OH + R' C OH
    H H 2. H3O+

    2. By oxidation of aldehydes and primary alcohols

    O O
    1. Ag2O or Ag(NH3)2+, OH-
    R CH R C OH
    2. H3O+

    1. KMnO4, OH-, heat O


    R CH2OH R C OH
    2. H3O+
    3. By oxidation of methyl ketones
    O O
    1. X2/NaOH
    C C + CHX3
    Ar CH3 Ar OH
    2. H2O+

    4. By hydrolisis of cyanohydrins and nitriles


    R OH HA R OH
    R C C
    C O + HCN
    R R CN H2O R CO2H

    5. By carbonation of Grignard reagents


    Mg 1.CO2
    CH3CH2Cl CH3CH2 MgCl CH3CH2CO2H
    Et2O 2. H3O+
    Exercise:

    • Show how each of the following compounds


    could be converted to benzoic acid:
    a. Ethylbenzene
    b. Bromobenzee
    c. Acetophenone
    d. Benzyl alcohol
    e. Benzaldehyde
    B. Synthesis of Acid Derivatives

    1. Synthesis of Acyl Chlorides


    O O
    R C OH + SOCl2 R C Cl + SO2 + HCl
    O O
    3 R C OH + PCl3 3 R C Cl + H3PO3

    2. Synthesis of Carboxilic acid anhydrides


    O O O O
    R C OH + Cl C R' + + Cl-
    R C O C R'
    N N +
    H
    3. Synthesis of ester: esterification
    O HA O
    R C OH + R'-OH R C OR' + H2O

    O -HCl O
    R C Cl + R'-OH R C OR'

    4. Synthesis amides
    O O
    R C Cl + 2 NH3 R C NH2 + NH4Cl

    O O O
    R C O C R'
    + 2 NH3 R C NH2 + RCO2-NH4+
    5. Nitriles from dehydration of amides
    O P4H10 or (CH3CO)2O
    R C N + H3PO3 or CH3CO2H
    R C NH2
    heat, -H2O

    Exercise:
    Show all steps in the synthesis of (CH3) 3 CCN
    from (CH3) 3 CCO2H

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