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    CHM 301 Organic Chemistry 11: Acid Chloride

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    WAN NUR AISYAH WAN AZIZAN
    Acid chlorides, also known as acyl chlorides, have the general formula RCOCl. They can be named using IUPAC or common nomenclature. Acid chlorides are prepared by reacting carboxylic acids with reagents like thionyl chloride or phosphorus trichloride. The main reactions of acid chlorides include hydrolysis, which produces carboxylic acids, ammonolysis to form amides, alcoholysis to form esters, and Friedel-Crafts acylation to add an acyl group to an aromatic ring.

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    CHM 301 Organic Chemistry 11: Acid Chloride

    Uploaded by

    WAN NUR AISYAH WAN AZIZAN
    40 views22 pages
    Acid chlorides, also known as acyl chlorides, have the general formula RCOCl. They can be named using IUPAC or common nomenclature. Acid chlorides are prepared by reacting carboxylic acids with reagents like thionyl chloride or phosphorus trichloride. The main reactions of acid chlorides include hydrolysis, which produces carboxylic acids, ammonolysis to form amides, alcoholysis to form esters, and Friedel-Crafts acylation to add an acyl group to an aromatic ring.

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    Acid chlorides, also known as acyl chlorides, have the general formula RCOCl. They can be named using IUPAC or common nomenclature. Acid chlorides are prepared by reacting carboxylic acids with reagents like thionyl chloride or phosphorus trichloride. The main reactions of acid chlorides include hydrolysis, which produces carboxylic acids, ammonolysis to form amides, alcoholysis to form esters, and Friedel-Crafts acylation to add an acyl group to an aromatic ring.

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    © All Rights Reserved
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    40 views22 pages

    CHM 301 Organic Chemistry 11: Acid Chloride

    Uploaded by

    WAN NUR AISYAH WAN AZIZAN
    Acid chlorides, also known as acyl chlorides, have the general formula RCOCl. They can be named using IUPAC or common nomenclature. Acid chlorides are prepared by reacting carboxylic acids with reagents like thionyl chloride or phosphorus trichloride. The main reactions of acid chlorides include hydrolysis, which produces carboxylic acids, ammonolysis to form amides, alcoholysis to form esters, and Friedel-Crafts acylation to add an acyl group to an aromatic ring.

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    of 22

    CHM 301

    ORGANIC CHEMISTRY 11

    ACID CHLORIDE
    SUBTOPICS

    1.0 General formula


    2.0 Nomenclature: IUPAC and
    common name
    3.0 Preparation
    4.0 Reactions
    1.0 GENERAL FORMULA

    2.0 NOMENCLATURE
    General formula O
    R C Cl
    Nomenclature
    i) IUPAC name
    - acid or acyl chlorides are named by replacing the
    suffix “-ic acid” with “-yl chloride”.
    O O
    H3C C OH H3C C Cl
    ethanoic acid ethanoyl chloride

    - carbonyl carbon atom is designated as C1.


    O O
    6 5 4 3 2
    CH3CH2CHCH2CCl CH3CH=CCH2CH2CCl
    5 4 3 2 1 1
    CH3 CH3
    3-methylpentanoyl chloride 4-methyl-4-hexenoyl chloride

    O O 2N O
    C Cl C Cl

    benzoyl chloride 3-nitrobenzoyl chloride


    - for acids that are named as alkanecarboxylic
    acids, the acid chlorides are named by using the
    suffix –carbonyl chloride.
    O
    C Cl
    cyclopentanecarbonyl chloride
    ii) Common name:

    O Br O
    CH3CH2CCl CH3CHCH2CCl
    IUPAC : propanoyl chloride IUPAC : 3-bromobutanoyl chloride
    Common: propionyl chloride Common: ß-bromobutyryl chloride
    3.0 PREPARATION OF
    ACID CHLORIDES
    PREPARATION OF ACYL CHLORIDES / ACID
    CHLORIDES

     Carboxylic acids reacts with phosphorus (v) chloride (PCl5) or


    sulphur dichloride oxide (thionyl chloride) or phosphorus
    trichloride (PCl3) at room temperature to form acyl chloride.
     In the case of benzoic acid, the reaction mixture is heated.
    O O
    R C OH PCl5 R C Cl POCl3 HCl
    carboxylic acids acid chlorides

    O O
    R C OH SOCl2 R C Cl SO2 HCl
    carboxylic acids acid chlorides

    O O
    3 R C OH PCl3 3 R C Cl H3PO3
    carboxylic acids acid chlorides
    Examples:

    O O
    CH3 C OH SOCl2 CH3 C Cl SO2 HCl
    ethanoic acid ethanoyl chloride

    O O
    C OH SOCl2 C Cl SO2 HCl
    benzoic acid benzoyl chloride
    4.0 REACTIONS OF ACYL CHLORIDES

    1. Hydrolysis
    2. Ammonolysis
    3. Alcoholysis
    4. Friedel-Craft acylation
    4.1 HYDROLYSIS

     Acyl chlorides react readily with water to form carboxylic acids.


     Occurs in aqueous base and at room temperature.
     When an acyl chloride is added with water, carboxylic acid and
    steamy acidic fumes of HCl are formed.

    O O
    R C Cl H-OH R C OH HCl

    O
    O H+ HCl
    R C OH
    R C Cl H-OH

    OH- O
    R C O Cl-
    MECHANISM FOR HYDROLYSIS OF ACYL
    EXAMPLE:
    CHLORIDES
    O H O
    H3C C Cl CH3 C OH HCl
    O H

     Step 1: Water attacks the carbonyl carbon causing the


    C=O to cleave.
    O H O
    CH3 C Cl CH3 C Cl
    O H
    O H

    Step 2: The elimination step occursHwhen π-bond forms


    between C and O and the chloride ion is removed.
    O
    O H
    CH3 C Cl
    CH3 C O H Cl
    O H
    H
    Step 3: H+ ion is removed by chloride ion to
    yield HCl.
    O H O
    CH3 C O H Cl CH3 C O H HCl
    4.2 AMMONOLYSIS

     Acyl chlorides react with ammonia, primary and secondary


    amines to form amides.
     The reaction is rapid and produce excellent yield.

    O O
    + -
    R C Cl 2NH3 R C NH2 NH4 Cl

    O O

    R C Cl 2RNH2 R C NHR RNH3+Cl-

    O O

    R C Cl 2R2NH R C NR2 R2NH2+Cl-


    MECHANISM FOR AMMONOLYSIS OF ACYL
    EXAMPLE:
    CHLORIDES
    O O
    H3C C Cl 2NH3 CH3 C NH2 NH +Cl-
    4

     Step 1: NH3 attacks the carbonyl carbon causing the C=O to


    cleave. O O
    CH3 C Cl NH3 CH3 C Cl
    NH3

    Step 2: The elimination step occurs when π-bond forms


    between C and O and the chloride ion is removed.
    O O
    CH3 C Cl CH3 C NH3 Cl

    NH3
    Step 3: H+ ion is removed by chloride ion to yield
    amide and HCl.
    O H O H
    CH3 C N H Cl CH3 C N H HCl
    H

    HCl NH3 NH4+Cl-


    The removal of H+ ion may also be done by the
    NH3 molecule.
    O H O H
    CH3 C N H NH3 CH3 C N H NH4+
    H

    +
    NH4 + Cl- NH4+Cl-
    4.3 ALCOHOLYSIS

     Acyl chloride react with an alcohol to produce an ester.


     Does not require catalyst even through alcohol is a weak
    nucleophile because acyl chloride is highly reactive.
     The reaction is irreversible unlike the reaction of carboxylic
    acid with alcohol.
     Pyridine is added to prevent side reaction between HCl and
    ROH.

    O O
    pyridine
    R C Cl R'-OH R C OR' HCl
     When pyridine is present, it removes HCl by reacting with it to
    yield pyridinium chloride salt.

    N HCl NHCl

     Acyl chloride also reacts with phenol to


    produce ester.
     The reaction is not as vigorous as the
    reaction of acyl chloride with alcohol.

    O OH O
    pyridine
    H 3C C Cl OCCH3 HCl
    MECHANISM FOR ALCOHOLYSIS OF ACYL
    EXAMPLE:
    CHLORIDES
    O O
    pyridine
    H3C C Cl CH3CH2 O H CH3 C OCH2CH3 HCl

     Step 1: Ethanol attacks the carbonyl carbon causing the


    C=O to cleave
    O O
    H3C C Cl CH3CH2 O H CH3 C Cl

    H O CH2CH3

    Step 2: The double bond of carbonyl carbon


    regenerates and pushes chloride ion out of the
    molecule.
    O O
    CH3 C Cl CH3 C OCH2CH3 Cl
    H O CH2CH3 H
    Step 3: H+ ion is removed by chloride ion to
    yield HCl.

    O O
    CH3 C OCH2CH3 Cl CH3 C OCH2CH3 HCl

    H
    4.4 FRIEDEL-CRAFTS ACYLATION
     An effective method of adding acyl group on the
    aromatic ring.
     Treating aromatic compound with an acyl chloride
    in the presence of a catalyst, AlCl3 to produce
    ketone.
    O
    H C R
    O
    AlCl3
    R C Cl HCl

    benzene ketone
    EXAMPLES:
    O
    C CH3
    O AlCl3
    HCl
    CH3CCl

    H3 C O
    AlCl 3 O H3 C
    Cl H3 C

    -CH3: ortho and para director O

    NO2 O
    NO2
    AlCl3
    Cl

    -NO2: meta director


    O
    The End….TQ 

    Love Organic Chemistry …in shaa Allah 

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