{"id":25797,"date":"2026-03-22T06:19:57","date_gmt":"2026-03-22T06:19:57","guid":{"rendered":"https:\/\/notes.aayo.blog\/?p=25797"},"modified":"2026-03-22T06:19:58","modified_gmt":"2026-03-22T06:19:58","slug":"carboxylic-acid-and-its-derivatives-2","status":"publish","type":"post","link":"https:\/\/notes.aayo.blog\/index.php\/2026\/03\/22\/carboxylic-acid-and-its-derivatives-2\/","title":{"rendered":"Carboxylic Acid and its derivatives"},"content":{"rendered":"\n

Introductions
Aromatic Carboxylic acid
Organic compounds containing carboxyl group (-COOH) as a functional group are called
carboxylic acid. The carboxyl group is the combination of the carbonyl & hydroxyl groups.<\/p>\n\n\n\n

General representation:
R\u2500 COOH or Ar \u2500 COOH
Where, R= alkyl groups (in aliphatic carboxylic acids) and Ar = aryl group usually Phenyl group (in
aromatic carboxylic acid)<\/p>\n\n\n\n

Nomenclature <\/p>\n\n\n\n

IUPAC format : Alkanoic Acid <\/p>\n\n\n\n

Aliphatic Carboxylic Acids <\/p>\n\n\n\n

Aromatic Carboxylic acid<\/p>\n\n\n\n

Isomerism
2) Functional Isomerism:
Example: Isomers of C2H4O2
Carboxylic acid shows following types of isomerism.
1) Chain Isomerism:
Example: Isomers of C4H8O2

2) From Nitriles (or Cyanides)
Alkane nitrile undergoes acidic hydrolysis to give carboxylic acid.
Question: Write the functional isomer of ethanoic acid & its IUPAC names.
<\/p>\n\n\n\n

2) From Nitriles (or Cyanides)
Alkane nitrile undergoes acidic hydrolysis to give carboxylic acid.
Question: Write the functional isomer of ethanoic acid & its IUPAC names.
General Methods of Preparation of Monocarboxylic acids
1) From Oxidation of Aldehydes
Aldehydes are easily oxidized into carboxylic acids by using oxidizing agents under normal conditions.
3) From Grignard\u2019s reagent (Carboxylation reaction)
Grignard reagent reacts with carbon dioxide in the presence of dry ether to form an addition product, which
on acid hydrolysis gives carboxylic acid.<\/p>\n\n\n\n

4) From Dicarboxylic Acid
When dicarboxylic acid is heated with glycerol, forms monocarboxylic acid.<\/p>\n\n\n\n

5) From Sodium Alkoxide
When sodium alkoxide reacts with carbon monoxide in presence of temperature and pressure, gives
sodium alkanoate, which on acidification efnrdil. HCl forms carboxylic acid.<\/p>\n\n\n\n

6) From Trihaloalkanes<\/p>\n\n\n\n

Question. What is meant by carboxylation reaction? Write an example of it.
Question. Give the chemical reaction for the preparation of ethanoic acid from
i) Sodium ethoxide ii) Ethane nitrile iii) Methyl magnesium iodide
iv) 1,1,1-Trichloroethane<\/p>\n\n\n\n

<\/p>\n\n\n\n

Preparation of Benzoic acid from Alkylbenzene
By Oxidation of Toluene
By Oxidation of Benzaldehyde<\/p>\n\n\n\n

Physical Properties of Monocarboxylic Acid
a)State, color, and odor: Lower members of carboxylic acids up to C10 are colorless unpleasant smelling
liquid while higher members are colorless, odorless waxy solids.
b) Solubility: The first four members are completely soluble in water because they can form
intermolecular hydrogen bonds with water molecules whereas higher members are insoluble in water due
to an increase in the hydrophobic nature of the hydrocarbon portion<\/p>\n\n\n\n

Question: The boiling point of Methanoic acid is higher than ethanol though they have same molecular
mass. Explain<\/p>\n\n\n\n

Question: The boiling point of Methanoic acid is higher than ethanol though they have same molecular
mass. Explain<\/p>\n\n\n\n

Question: The boiling point of Methanoic acid is higher than ethanol though they have same molecular
mass. Explain<\/p>\n\n\n\n

Chemical Properties of Aliphatic and Aromatic carboxylic acids<\/p>\n\n\n\n

1)Acidic nature:<\/p>\n\n\n\n

Carboxylic acids are more acidic in nature than aliphatic alcohols because the carboxylate ion forme
after the ionization of carboxylic acid is resonance stabilized whereas alkoxide ion formed after the
ionization of alcohol is not resonance stabilized. More the stability of ions in an aqueous solution higher
will be the acid strength.
Example: Acetic acid (Ethanoic acid) is a stronger acid than Ethanol<\/p>\n\n\n\n

Effect of Substituent on acidic strength of Carboxylic Acid
i) Electron donating groups such as \u2212CH3, \u2212OH, \u2212NH2, etc. donates the electrons and shows + I effect
which destabilizes the carboxylate anion by intensifying the negative charge on the oxygen atom & decrease
the acid strength of carboxylic acid.<\/p>\n\n\n\n

Example:<\/p>\n\n\n\n

Question: Why is ethanoic acid (acetic acid) weaker acid than Methanoic acid (Formic acid)?
ii) Electron withdrawing groups such as \u2212F, \u2212Cl, \u2212Br, \u2212I, \u2212CN, \u2212NO2, etc. withdraw the electrons and
shows the \u2212 I effect, which stabilizes the carboxylate anion by dispersing the negative charge on the oxygen atom
& increase the acid strength of carboxylic acid.<\/p>\n\n\n\n

Example:<\/p>\n\n\n\n

Question: Why is Chloroacetic acid stronger acid than acetic acid?
Effect of Substituent on acidic strength of Benzoic Acid
Benzoic acid is less acidic than formic acid but more acidic than acetic acid because the phenyl group (\u2212C6H
is a weak electron-releasing group than the \u2212CH3 group of acetic acid. \u2212CH3 group intensify the negative char
more in acetate ion and destabilize than the \u2212C6H5 group in benzoate ion.
Example:
Decreasing Order of acidic strength: HCOOH > C6H5COOH> CH3COOH
Electron donating substituent (-OH, -NH2, -CH3, etc.) decreases the acidic strength of benzoic acid
whereas electron-withdrawing substituent (-NO2, -Cl, -Br, -I, -CN, etc.) increases the acidic strength
benzoic acid.
For example:<\/p>\n\n\n\n

Reactions to show the acidic nature of carboxylic acid<\/p>\n\n\n\n

Laboratory Test of Carboxylic Acid<\/p>\n\n\n\n

Carboxylic acid reacts with sodium carbonate or sodium bicarbonate & produces brisk effervescence of
carbon dioxide gas whereas other weak acids like alcohol & phenols do not react with sodium
carbonate or sodium bicarbonate.<\/p>\n\n\n\n

Other Important Reactions:<\/p>\n\n\n\n

Electrophilic Substitution Reaction of Benzoic Acid
\u2212COOH group is meta directing group. Due to resonance in benzoic acid, electron density
decreases more at the ortho and para positions as compared to the meta positions. Hence, the incoming
electrophile will prefer to attack the meta position during the electrophilic substitution
reactions.<\/p>\n\n\n\n

Some examples of electrophilic substitution reactions are as follows:<\/p>\n\n\n\n

Uses of Benzoic acid
Salt of benzoic acid i.e. sodium benzoate is used as a food preservative.
Esters of benzoic acid are used in perfumery.
Used in organic synthesis (dyes, drugs).<\/p>\n\n\n\n

Formic acid (Methanoic acid)<\/p>\n\n\n\n

Formic acid differs from other carboxylic acid because it contains both carboxyl group (\u2212COOH)
and aldehyde (\u2212CHO) group. So, it behaves as both acid as well an aldehyde<\/p>\n\n\n\n

Acidic Nature:<\/p>\n\n\n\n

Abnormal behavior of Methanoic acid (or Formic acid):<\/p>\n\n\n\n

Difference between properties of HCOOH & CH3COOH<\/p>\n\n\n\n

USES:<\/p>\n\n\n\n

    \n
  1. Formic acid is used in leather tanning, the textile industry for the dying process,<\/li>\n\n\n\n
  2. It is used in the preparation of carbon monoxide.<\/li>\n\n\n\n
  3. It is used in medicine for the treatment of gout.<\/li>\n\n\n\n
  4. Acetic acid is used in plastic and rubber industries, as a coagulant in the manufacture of rubber from
    latex and casein from milk, as vinegar, and as a solvent.<\/li>\n<\/ol>\n\n\n\n

    Aliphatic and Aromatic Derivatives of Carboxylic Acid
    IUPAC Nomenclature:
    O
    Functional Group: CCl
    Aliphatic Derivative: \u201cAlkanoyl halide\u201d
    Aromatic derivative: \u201cBenzoyl halide\u201d
    Examples:
    The organic compounds formed by the replacement of the \u2013OH group of carboxylic acid by electron
    rich species like -X (halo), -NH2 (Amino), -OR (Alkoxy), and \u2013OCOR group are known as derivatives
    of
    carboxylic acid.
    These derivatives are either aliphatic or aromatic in nature.
    i.e<\/p>\n\n\n\n

    [A] Acid Halide or Acyl halide<\/p>\n\n\n\n

    IUPAC Nomenclature:
    O
    Functional Group: CCl
    Aliphatic Derivative: \u201cAlkanoyl halide\u201d
    Aromatic derivative: \u201cBenzoyl halide\u201d
    Examples<\/p>\n\n\n\n

    Aliphatic Acid halide<\/p>\n\n\n\n

    Aliphatic Acid halide<\/p>\n\n\n\n

    [B] Acid Amides<\/p>\n\n\n\n

    IUPAC Nomenclature: Functional Group:
    Aliphatic Derivative: \u201cAlkanamide\u201d
    Aromatic derivative: \u201cBenzamide\u201d
    Examples:<\/p>\n\n\n\n

    Aliphatic Acid Amide<\/p>\n\n\n\n

    Aromatic Acid Amide<\/p>\n\n\n\n

    [C] Esters
    Aliphatic Esters
    IUPAC
    Nomenclature:
    Functional Group:
    Secondary suffix: -oate
    Aliphatic Derivative: \u201c\u2026.. alkanoates\u201d
    Aromatic derivative: \u201c\u2026\u2026benzoate\u201d
    Examples:<\/p>\n\n\n\n

    Aliphatic Esters<\/p>\n\n\n\n

    Aromatic Esters<\/p>\n\n\n\n

    [D] Acid Anhydride<\/p>\n\n\n\n

    IUPAC Nomenclature: Functional
    Group: Secondary suffix: -oic anhydride
    IUPAC Name: \u201c\u2026.. oic anhydride\u201d
    Examples:<\/p>\n\n\n\n

    Aliphatic Acid Anhydride<\/p>\n\n\n\n

    Aromatic Acid Anhydride<\/p>\n\n\n\n

    Claisen Condensation
    Hofmann-Bromamide reaction(Decarbonylation reaction)
    This reaction is used to decrease the carbon chain by one carbon atom.
    When \u03b1-hydrogen containing esters undergoes condensation reaction in the presence of a strong base
    like sodium ethoxide, then \u03b2-keto ester is formed. This reaction is called the Claisen condensation
    reaction.
    For example:<\/p>\n\n\n\n

    Hofmann-Bromamide reaction(Decarbonylation reaction)<\/p>\n\n\n\n

    When primary amide is heated with bromine in the presence of aqueous NaOH or KOH solution, then<\/p>\n\n\n\n

    <\/p>\n\n\n\n

    Example:<\/p>\n\n\n\n

    Note: This reaction is used to decrease the carbon chain by one carbon atom.<\/p>\n\n\n\n

    Comparative Study of Physical Properties of Acid Derivatives<\/p>\n\n\n\n

    Relative reactivity of Acid derivatives<\/p>\n\n\n\n

    The reactivity order of acid derivatives toward nucleophilic substitution follows the order;<\/p>\n\n\n\n

    <\/p>\n","protected":false},"excerpt":{"rendered":"

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