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    Chapter 7 - Carboxylic Acids

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    Roy Zahreddine
    This document summarizes key points about carboxylic acids from an organic chemistry course. It discusses IUPAC naming of carboxylic acids, their physical properties including boiling points and dimer formation, acidity and pKa values, salt formation reactions, saponification reactions, and common synthesis and important examples of carboxylic acids.

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    © All Rights Reserved
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    Chapter 7 - Carboxylic Acids

    Uploaded by

    Roy Zahreddine
    30 views8 pages
    This document summarizes key points about carboxylic acids from an organic chemistry course. It discusses IUPAC naming of carboxylic acids, their physical properties including boiling points and dimer formation, acidity and pKa values, salt formation reactions, saponification reactions, and common synthesis and important examples of carboxylic acids.

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    Chapter 7 - Carboxylic acids

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    This document summarizes key points about carboxylic acids from an organic chemistry course. It discusses IUPAC naming of carboxylic acids, their physical properties including boiling points and dimer formation, acidity and pKa values, salt formation reactions, saponification reactions, and common synthesis and important examples of carboxylic acids.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    30 views8 pages

    Chapter 7 - Carboxylic Acids

    Uploaded by

    Roy Zahreddine
    This document summarizes key points about carboxylic acids from an organic chemistry course. It discusses IUPAC naming of carboxylic acids, their physical properties including boiling points and dimer formation, acidity and pKa values, salt formation reactions, saponification reactions, and common synthesis and important examples of carboxylic acids.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 8

    12/15/2020

    CHEM331 ‐ Organic Chemistry (3 cr.)
    Fall 2020‐2021

    Course Instructor: Jean El Achkar, PhD, Assistant Professor
    E‐mail: [email protected]

    Chapter 7: Carboxylic acids

    Introduction
    The functional group of carboxylic acids consists of a C=O
    with ‐OH bonded to the same carbon.
    Carboxyl group is usually written ‐COOH.
    Aliphatic acids have an alkyl group bonded to ‐COOH.
    Aromatic acids have an aryl group.

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    12/15/2020

    IUPAC Names

    Remove ‐e from alkane (or alkene) name, add ‐oic acid.


    The carbon of the carboxyl group is #1.

    Ph H
    Cl O C C
    CH3CH2CHC OH H COOH

    2‐chlorobutanoic acid trans‐3‐phenyl‐2‐propenoic acid 
    (cinnamic acid)

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    12/15/2020

    Physical Properties: Boiling Points

     Higher boiling points than similar alcohols, due to dimer


    formation.
     A chemical entity consisting of two structurally similar monomers
    joined by bonds.

    Acetic acid, b.p. 118C
    5

    Physical Properties:
    Melting Points

     Aliphatic acids with more than 8 carbons are solids at


    room temperature.
     Double bonds (especially cis) lower the melting point.
     Note these 18‐C acids:
     Stearic acid (saturated): 72C
     Oleic acid (one cis double bond): 16C
     Linoleic acid (two cis double bonds): ‐5C

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    12/15/2020

    Acidity

     A carboxylic acid may dissociate


    in water to give a proton and a
    carboxylate ion.
     The equilibrium constant Ka for
    this reaction is called the acid‐
    dissociation constant.
     The pKa of an acid is the negative
    logarithm of Ka, and we
    commonly use pKa as an
    indication of the relative acidities
    of acids.

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    12/15/2020

    Salts of Carboxylic Acids

    Sodium hydroxide removes a proton to form the salt.

    Adding a strong acid, like HCl, regenerates the carboxylic acid.

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    Saponification

     “Soap‐making”
     Base‐catalyzed hydrolysis of ester linkages in fats and oils.

    O CH2 OH
    CH2 O C (CH2)16CH3 CH OH
    O
    CH2 OH
    CH O C (CH2)16CH3 + 3 NaOH
    O O
    +-
    CH2 O C (CH2)16CH3 + 3 Na O C (CH2)16CH3

    Soap

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    11

    Synthesis Review
    Oxidation of primary alcohols and aldehydes with
    chromic acid.
    Cleavage of an alkene with hot KMnO4 produces a
    carboxylic acid if there is a hydrogen on the double‐
    bonded carbon.
    Alkyl benzene oxidized to benzoic acid by hot KMnO4 or
    hot chromic acid.

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    12

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    Synthesis

    Oxidation of primary alcohols and aldehydes with 
    chromic acid.

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    Synthesis

    Cleavage of an alkene with hot KMnO4 produces a 
    carboxylic acid if there is a hydrogen on the double‐
    bonded carbon.

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    Synthesis

    Alkyl benzene oxidized to benzoic acid by hot KMnO4 or 


    hot chromic acid. 

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    Some Important Acids

    Acetic acid is in vinegar and other foods, used industrially 
    as solvent, catalyst, and reagent for synthesis.
    Fatty acids from fats and oils.
    Benzoic acid in drugs, preservatives.
    Adipic acid used to make nylon 66.
    Phthalic acid used to make polyesters.

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