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    Chapter 21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

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    張湧浩
    The document describes reactions involving carboxylic acid derivatives. It discusses nucleophilic acyl substitution reactions where an alcohol reacts with a carboxylic acid to form an ester and a carboxylate ion. It also describes similar reactions where an amine reacts with an ester to form an amide and an alcohol. The document provides examples of hydrolysis, reduction, and anhydride formation reactions.

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    Chapter 21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

    Uploaded by

    張湧浩
    91 views20 pages
    The document describes reactions involving carboxylic acid derivatives. It discusses nucleophilic acyl substitution reactions where an alcohol reacts with a carboxylic acid to form an ester and a carboxylate ion. It also describes similar reactions where an amine reacts with an ester to form an amide and an alcohol. The document provides examples of hydrolysis, reduction, and anhydride formation reactions.

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    problem_chp21-4

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    The document describes reactions involving carboxylic acid derivatives. It discusses nucleophilic acyl substitution reactions where an alcohol reacts with a carboxylic acid to form an ester and a carboxylate ion. It also describes similar reactions where an amine reacts with an ester to form an amide and an alcohol. The document provides examples of hydrolysis, reduction, and anhydride formation reactions.

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    91 views20 pages

    Chapter 21. Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

    Uploaded by

    張湧浩
    The document describes reactions involving carboxylic acid derivatives. It discusses nucleophilic acyl substitution reactions where an alcohol reacts with a carboxylic acid to form an ester and a carboxylate ion. It also describes similar reactions where an amine reacts with an ester to form an amide and an alcohol. The document provides examples of hydrolysis, reduction, and anhydride formation reactions.

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    Chapter 21.

    Carboxylic Acid
    Derivatives: Nucleophilic Acyl
    Substitution Reactions
    21.1 O O
    CH3OH
    C C
    CH3CH2 O CH2CH3

    • Ethanoic acid + ethanol


    • methyl ethanoate + Propanoic acid
    • ethyl ethanoate + Ethanoic acid
    • methyl propanoate + Propanoic acid
    • ethyl propanoate + Ethanoic acid
    21.1 answer
    • Ethanoic acid + ethanol
    • methyl ethanoate + Propanoic acid
    • ethyl ethanoate + Ethanoic acid
    • methyl propanoate + Propanoic acid
    • ethyl propanoate + Ethanoic acid

    An anhydride reacts with an alcohol to give a carboxylic acid


    and an ester.
    Alcoholysis 醇解
    O
    21.2
    CH3CH2CH2NH2
    C
    CH3CH2 OCH3

    • N-Propyl propanamide + methanol


    • N-Propyl ethanamide + ethanol
    • N-Ethyl propanamide + methanol
    • N-Ethyl ethanamide + ethanol
    • N-Ethyl ethanamide + propanol
    Level 3
    Challenging
    21.2 answer

    • N-Propyl propanamide + methanol


    • N-Propyl ethanamide + ethanol
    • N-Ethyl propanamide + methanol
    • N-Ethyl ethanamide + ethanol
    • N-Ethyl ethanamide + propanol
    Aminolysis 胺解
    An ester reacts with an amine to produce an amide
    and an alcohol.
    Level 3
    Challenging
    O
    21.3 HCl
    C
    CH3CH2 NHCH3 heat

    O
    O
    (a) (b)
    NH2
    H

    (c) CH3COOH (d)


    COOH
    21.3 answer
    O
    O
    (a) (b)
    NH2
    H

    (c) CH3COOH (d)


    COOH

    Hydrolysis 水解
    21.4
    Predict the outcome of the following
    reaction.
    O

    OH SOCl2

    1. 2. 3.
    O O
    OH
    H Cl

    4. 5.
    O
    O
    S
    OH S OH
    O
    21.4 answer
    O

    OH SOCl2

    1. 2. 3.
    O O
    OH
    H Cl

    4. 5.
    O
    O
    S
    OH S OH
    O
    O
    21.5 1. 2CH3MgBr
    C
    +
    CH3CH2 Cl 2. H3O

    (a) (b)

    HO
    OH

    (c) (d)

    OH HO
    21.5 answer

    (a)
    (b)
    HO
    OH

    (c) (d)

    OH HO
    21.6 O
    1) LiAlH4

    NH2 2) H2O

    O
    (a) COOH (b)

    NH2

    (d)
    (c)
    CH2NH2 CH2NHCH3
    21.6 answer

    O
    (a) COOH (b)

    NH2

    (d)
    (c)
    CH2NH2 CH2NHCH3
    21.7 O
    1) LiAlH4

    NHCH3 2) H2O

    O
    (a) COOH (b)

    NH2

    (d)
    (c)
    CH2NH2 CH2NHCH3
    21.7 answer

    O
    (a) COOH (b)

    NH2

    (c) (d)
    CH2NH2 CH2NHCH3
    O O
    21.8
    C C
    CH3CH2 Cl
    + -
    HO CH3

    a.Ethanoic methanoic anhydride


    b.Methanoic propanoic anhydride
    c.Ethanoic anhydride
    d.Ethanoic propanoic anhydride
    21.8 Answer

    a.Ethanoic methanoic anhydride


    b.Methanoic propanoic anhydride
    c.Ethanoic anhydride
    d.Ethanoic propanoic anhydride

    An acid halide reacts with a carboxylic acid


    to form an anhydride.
    21.9
    What sequence of reagents will accomplish the
    following transformation?
    OH
    OH

    1. 2.
    + +
    H 2 PhMgBr H3O H3O+
    2 PhMgBr
    CH3OH Et2O Et2O

    3. 4.
    H+ H+ 2 PhOH

    PhOH CH3OH

    5.
    SOCl2 2 PhOH
    21.9 answer
    OH
    OH

    1.
    +
    2.
    H +
    2 PhMgBr H3O 2 PhMgBr H3O+

    CH3OH Et2O Et2O

    3. 4.
    H+ H+ 2 PhOH

    PhOH CH3OH

    5.
    SOCl2 2 PhOH
    1.

    5.

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