Carboxylic Acid
A carboxylic acid is an organic compound that contain carboxyl group [C (=O) OH]. The general formula of carboxylic acid is R
example include the amino acid and acetic group. Deportonation of carboxylate anion.
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1 Nomenclature
Carboxylic acids are commonly identified by their trivial names. They are often have the suffix – OIC ACID. For example butyric acid [
complex molecules containing a carboxylic acid, he carboxyl can be considered position one of the parent chain even if there are othe
Alteternatly it can be named as a ‘carboxyl’ or carboxylic acid substituent on another parent structure.
The carboxylate anion (R-COO OR RCO) of a carboxylic acid is usually named with the suffix –ate, in keeping with the general of –ic aci
bas, respectively. For example, the conjugate base of acetic acid is acetate.
2. Example- straight- chain, saturated carboxylic acid
.n Carbon atom Common name IUPAC name Chemical formula Common use
1 1 Carbonic acid Carbonic acid OHCOOH Blood and tissue
2 1 Formic acid Methanoic acid HCOOH Insect sting
3 2 Acetic acid Ethanoic acid CH3COOH Vinegar
4 3 Propionic acid Propanoic acid CH2CH3COOH Preservation milk
5 4 Butyric acid Butanoic acid CH2(CH2)2COOH Butter
6 5 Valeric acid Pentanoic acid valerian
7 6 Caproic acid Hexanoic acid CH3(CH2)4COOH Goat fat
8 7 Enanthic acid Heptanoic acid CH3(CH2)5COOH enantic
9 8 Caprylic acid Octanoic acid CH3(CH2)6COOH Coconut
10 9 Pelargonic acid Nonanoic acid CH3(CH2)7COOH Pelargonium
11 10 Capric acid Decanoic acid CH3(CH2)8COOH Palm kernel oil
12 11 Undecylic acid Undecanoic acid CH3(CH2) COOH
13 12 Lauric acid Dodecanoic acid CH3(CH2)10COOH Soap , hand wash
14 13 Tridecyclic acid Tridecanoic acid CH3(CH2)11COOH
15 14 Myristic acid Tetradecanoic acid CH3(CH2)12COOH Nutmeg
16 15 Pentadecylic acid Pentadecanoic acid CH3 (CH2)13COOH
17 16 Palmitic acid hexadecanoic acid CH3( CH2)14 COOH Palm oil
18 17 Margaric acid Heptadecanoic acid CH3(CH2)15 COOH
19 18 Stearic acid Octadecanoic acid CH3 (CH2)16 COOH Chocolate , waxes
20 19 Nonadecylic acid Nonadecanoic acid CH3(CH2)17COOH Fats, vegetable oils
21 20 Arachidic acid Icosanoic acid CH3 (CH2)18 COOH Peanut oil
3. Other carboxylic acids
Compound class Members
Unsaturated Acrylic acid –CH=CHCOOH used in polymer synthesis
monocarboxylic acid
atty acid Medium to long chain saturated monocarboxylic acid with even no of carbon
Amino acid The building blocks of proteins
eto acid Acids of biochemical significance that contain ketone group . eg. Pyruvic acid
Aromatic carboxylic acids Containting atleast one aromatic ring . eg. Benzoic acid , saliclylic acid
Dicarboxylic acid Containing two carboxyl group . eg. Adipic acid , aldaric acid
ricarboxylic acids Containing three carboxyl group eg. Citric acid , isocitric acid
Alpha hydroxy acids Containing a hydroxyl group eg. Glyceric acid, lactic acid
Divinylether fatty acid Containing a doubly unsaturated carbon chain attached via an ether bond to a fatty acid
found in some plant
4. Physical properties
[1]. Solubility
Carboxylic acid are polar . because they are both hydrogen – bond acceptor and hydrogen bond donar , they also participate in hydrog
nonpolar media due to therir tendency to ‘ self associate’ . smaller carboxylic acids are soluble in water , whereas higher carboxylic ac
hydrophobic nature of the alkyl chain .these longer chain acid tend to be soluble in less polar solvents such as ethers and alcohol.
[2]. Boiling points
Carboxylic acids tend to have higher boiling points than water , because of their greater surface areas and their tendencyto form stabi
boiling to occur , either the dimer bonds must be broken or either dimer arrangement must be vapourised , increasing the enthalpy o
[3]. Acidity
Carboxylic acid are bronsted – Lowry acids because they are proton donor. they are the most common type of organic acid. Carboxyli
they only partially dissociate into H3O cation and RCOO anions in neutral aqueous solution .
Carboxylic acid pKa
Acetic acid 4.76
Benzoic acid 4.2
Formic acid 3.75
Chloroacetic acid 2.86
Dichloroacetic acid 1.29
Oxalic acid 1.27
Trichloroacetic acid 0.65
Trifluoroacetic acid 0.23
Deprotonation of carboxylic acids gives carboxylate anions these are resonance stabilized, because the negative charge is delocalized
stability of the anion. Each of carbon oxygen bonds in the carboxylate anion has a partial double bond character.
[4].odor
Carboxylic acids often have strong sour odors. Esters of carboxylic acids tends to have pleasant odor and many are used in the prepara
[5]. Occurrence
Many carboxylic acids are produced industrially on a large scale. They are also frequently found in nature. Esters of fatty acid are the m
amino carboxylic acids are the main component of protein.
[6]. Application
Carboxylic acids are used in the production of polymers, pharmaceuticals, solvents and the food additives additives. Industrially impor
(component of vinegar, precursor, to solvents and coatings) acrylic and methacrylic acids (precursor to polymers, adhesives)
Adipic (polymers) citric acid (a flavor and preservative in food and beverages) fatty acids (coating), maleic acid (polymers), propionic a
salts are soaps.
5. Synthesis
[1]. Laboratory methods
Preservation methods for small scale reactions for research or for the production of fine chemicals often employ expensive consumab
1. Oxidation of primary alcohol or aldehyde with strong oxidants such s potassium dichromate, jones reagent, potassium perman
2. Oxidation cleavage of olefins by ozonolysis , potassium permanganate or potassium dichromate
3. Hydrolysis of nitriles, esters and amides usualltuy with acid or base catalysis.
4. Carbonation of Grignard reagent and organolithium reagent.
5. Halogenation is followed by the hydrolysis of methyl ketones in the haloform reaction.
6. Disproportionate of an aldehyde in the cannizzaro reaction .
5. Systematic Nomenclature of Substituted
Dicarboxylic Acids
The systematic name of an aliphatic dicarboxylic acid is derived by:
First identifying the parent chain that contains the two carboxylic acid groups and then adding a suffix -dioic acid to the na
The parent chain is numbered from the end that gives the substituents in the chain the lowest possible address number.
The substituents are arranged in alphabetical order in the full name of the dicarboxylic acid.
6. Acidity of Aromatic Carboxylic Acids
Benzoic acid is the simplest of aromatic carboxylic acids.
Two factors influence the acidity of substituted aromatic carboxylic acids: The resonance effect and the induct
operates through -bonds, the resonances effect operates by electron or charge delocalization through π–bond
7. Acidity of Aromatic Carboxylic Acids: the
Resonance Effect
When both resonance and inductive effects apply in a specified substrate, the resonance effect dominates t
order of acidity among isomeric carboxylic acids.
The carboxylate anion obtained in the ionization of aromatic carboxylic acids is best stabilized when there are
to the aromatic nucleus.
It is for this reason that the nitrobenzoic acid derivatives, with the highly electro withdrawing nitro group are st
8.Ozonolysis of Alkynes to Carboxylic Aci
Ozonolysis of alkynes under hydrolytic conditions lends access to carboxylic acids.
Terminal alkynes are strategic substrates in the synthesis of carboxylic acids because the methanoic acid form
the other carboxylic acid relatively pure.
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