This document discusses the nomenclature, physical properties, preparation, and reactions of carboxylic acids. It begins by defining carboxylic acids and how they are classified. Rules of IUPAC nomenclature for aliphatic, cyclic, and aromatic carboxylic acids are provided. Key physical properties like solubility and boiling point are attributed to hydrogen bonding. Carboxylic acids are described as stronger acids than alcohols or phenols due to resonance stabilization of the conjugate base. Common methods for preparing carboxylic acids include oxidation reactions and hydrolysis of nitriles. Characteristic reactions include forming salts with bases, and generating acid derivatives like esters, acid chlorides, anhydrides, and am
Aldehydes and ketones are organic compounds which incorporate a carbonyl functional group, C=O. The carbon atom of this group has two remaining bonds that may be occupied by hydrogen or alkyl or aryl substituents. If at least one of these substituents is hydrogen, the compound is an aldehyde.
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containing a carbonyl group is often referred to as a carbonyl compound.
Aldehydes and ketones are organic compounds which incorporate a carbonyl functional group, C=O. The carbon atom of this group has two remaining bonds that may be occupied by hydrogen or alkyl or aryl substituents. If at least one of these substituents is hydrogen, the compound is an aldehyde.
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. A compound containing a carbonyl group is often referred to as a carbonyl compound.
Preparation and reaction of aldehyde and ketone, electromeric effect, aldol condensation, cannizarro reaction, perkin condensation, benzoin condensation, nucleophilic addition reaction and uses of aldehyde and ketone
The combination of a carbonyl group and a hydroxyl on the same carbon atom is called a carboxyl group. Compounds containing the carboxyl group are called carboxylic acids. The carboxyl group is one of the most widely occurring functional groups in organic chemistry.
Aromatic Carboxylic acids: Carboxylic acids have an aryl group bound to the carboxyl group is known as aromatic carboxylic acids. The general formula of an aliphatic aromatic carboxylic acid is Ar-COOH.
Acidity of carboxylic acid:
A carboxylic acid may dissociate in water to give a proton and a carboxylate ion. Dissociation of a carboxylic acid involves breaking an O-H bond gives a carboxylate ion with the negative charge spread out equally over two oxygen atoms, compared with just one oxygen atom in an alkoxide ion. The delocalized charge makes the carboxylate ion more stable therefore; dissociation of a carboxylic acid to a carboxylate ion is less endothermic.
Preparation Methods:
1. Oxidation:
The oxidation of aldehyde with oxidizing agents such as CrO3 to forms carboxylic acids containing the same numbers of carbon atoms with a oxidizing agents like chromic acid, chromium trioxide. The silver oxide (Ag2O) in aqueous ammonia solution (Tollen’s reagent) is mild reagent give good yield at room temperature. E.g. Acetaldehyde reacts with CrO3 in aqueous acid to give acetic acid.
2. Grignard reagents (from CO2):
Carboxylic acid can be prepared by the reaction of Grignard reagent (alkyl magnesium halide) with carbon dioxide (CO2) in presence of dry ether. Grignard reagents react with carbon dioxide to forms a magnesium carboxylates which on hydrolysis by dilute HCl produces carboxylic acids.
3. Hydrolysis of nitrile:
The hydrolysis of nitrile or cyanide in presence of dilute acid to forms a carboxylic acid. In this reaction –CN group is converted to a –COOH group.
4. Hydrolysis Reactions:
All the carboxylic acid derivatives can be hydrolyzed into the carboxylic acid in the acidic or basic media; the hydrolysis reaction is fast and occurs in presence of water with no acid or base catalyst.
1. From Ester (Hydrolysis of ester): Ester can be hydrolyzed in either acidic or basic medium to yield carboxylic acid. The ester is heated with an excess of water contains strong acid or base catalyst.
Properties of Carboxylic Acids:
1. Low molecular weights carboxylic acids are colourless liquid at room temperature i.e. lower member ate liquid up to C9 and have characteristic odors whereas higher members are solid.
2. Carboxylic acids are polar organic compound. Low molecular weight carboxylic acids (first four members) are soluble in water whereas solubility in water decrease as molecular weight and chain lengthing increases.
3. Aromatic acids are insoluble in water.
4. Carboxylic acids have higher melting and boiling point due to their capacity to readily form stable hydrogen-bonded dimers.
Preparation and reaction of aldehyde and ketone, electromeric effect, aldol condensation, cannizarro reaction, perkin condensation, benzoin condensation, nucleophilic addition reaction and uses of aldehyde and ketone
The combination of a carbonyl group and a hydroxyl on the same carbon atom is called a carboxyl group. Compounds containing the carboxyl group are called carboxylic acids. The carboxyl group is one of the most widely occurring functional groups in organic chemistry.
Aromatic Carboxylic acids: Carboxylic acids have an aryl group bound to the carboxyl group is known as aromatic carboxylic acids. The general formula of an aliphatic aromatic carboxylic acid is Ar-COOH.
Acidity of carboxylic acid:
A carboxylic acid may dissociate in water to give a proton and a carboxylate ion. Dissociation of a carboxylic acid involves breaking an O-H bond gives a carboxylate ion with the negative charge spread out equally over two oxygen atoms, compared with just one oxygen atom in an alkoxide ion. The delocalized charge makes the carboxylate ion more stable therefore; dissociation of a carboxylic acid to a carboxylate ion is less endothermic.
Preparation Methods:
1. Oxidation:
The oxidation of aldehyde with oxidizing agents such as CrO3 to forms carboxylic acids containing the same numbers of carbon atoms with a oxidizing agents like chromic acid, chromium trioxide. The silver oxide (Ag2O) in aqueous ammonia solution (Tollen’s reagent) is mild reagent give good yield at room temperature. E.g. Acetaldehyde reacts with CrO3 in aqueous acid to give acetic acid.
2. Grignard reagents (from CO2):
Carboxylic acid can be prepared by the reaction of Grignard reagent (alkyl magnesium halide) with carbon dioxide (CO2) in presence of dry ether. Grignard reagents react with carbon dioxide to forms a magnesium carboxylates which on hydrolysis by dilute HCl produces carboxylic acids.
3. Hydrolysis of nitrile:
The hydrolysis of nitrile or cyanide in presence of dilute acid to forms a carboxylic acid. In this reaction –CN group is converted to a –COOH group.
4. Hydrolysis Reactions:
All the carboxylic acid derivatives can be hydrolyzed into the carboxylic acid in the acidic or basic media; the hydrolysis reaction is fast and occurs in presence of water with no acid or base catalyst.
1. From Ester (Hydrolysis of ester): Ester can be hydrolyzed in either acidic or basic medium to yield carboxylic acid. The ester is heated with an excess of water contains strong acid or base catalyst.
Properties of Carboxylic Acids:
1. Low molecular weights carboxylic acids are colourless liquid at room temperature i.e. lower member ate liquid up to C9 and have characteristic odors whereas higher members are solid.
2. Carboxylic acids are polar organic compound. Low molecular weight carboxylic acids (first four members) are soluble in water whereas solubility in water decrease as molecular weight and chain lengthing increases.
3. Aromatic acids are insoluble in water.
4. Carboxylic acids have higher melting and boiling point due to their capacity to readily form stable hydrogen-bonded dimers.
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Carboxylic acid derivatives
1. 1
BY
VANA JAGAN MOHAN RAO M.S.Pharm, MED.CHEM
NIPER-KOLKATA
Asst.Professor, MIPER-KURNOOL
Email: jaganvana6@gmail.com
2. Carboxylic acids are strong organic acids which contain
the carboxyl group (-COOH, -CO2H)
Carboxylic acids are classified as aliphatic or aromatic depending
on whether R or an Ar is attached to the carboxylic group
R-COOH or Ar-COOH
C
O
O H
2
5. • Identify longest chain
• (IUPAC) Number carboxyl carbon as 1
• (Common) Assign , , , to carbon atoms
adjacent to carboxyl carbon
RULES OF NOMENCLATURE
Examples:
5
6. Cyclic compounds containing one or more COOH groups attached to
the ring are named by identifying the name of the ring followed
by the word carboxylic acid or dicarboxylic acids etc.
NOMENCLATURE OF CYCLIC CARBOXYLIC ACIDS
6
7. The carbon atom bearing the carboxylic group is numbered 1
and the substituents are numbered relative to it.
7
8. Salicylic acid
2-Hydroxybenzoic acid
NOMENCLATURE OF AROMATIC CARBOXYLIC
ACIDS
The simplest aromatic carboxylic acid is benzoic acid.
Substituted benzoic acids are named with benzoic acid as
the parent name.
Derivatives are named using numbers to show the location
of substituents relative to the carboxyl group.
The ring carbon attached to the carboxyl group is the #1 position.
Benzoic acid
Benzene carboxylic acid
8
4-hydroxy-3-methoxybenzoic acid
10. PHYSICAL PROPERTIES OF CARBOXYLIC ACIDS
1. Solubility
The carboxylic acid are highly polar organic compounds.
This polarity results from the presence of a strongly polarized
carbonyl (C=O) group and hydroxyl (O-H) group.
As the number of carbons in a carboxylic acid series becomes
greater, the solubility in water decreases.
Aromatic carboxylic acids are insoluble in water. 10
11. 2. Boiling Point
Carboxylic acids are polar compounds and form very strong
intermolecular hydrogen bonds to form a dimer.
As the number of carbons in a carboxylic acid series becomes
greater, the boiling point increases.
11
12. ACIDITY AND ACID STRENGTH
The most important chemical property of carboxylic acids
chemistry is their acidic nature.
The mineral acids (HCl, HBr, HI, H2SO4, H3PO4 ) are defined as
"strong acids" because they undergo complete dissociation.
Carboxylic acids are strong organic acids , they are much more
acidic than alcohols.
Carboxylic acids are stronger acids than phenols.
12
13.
14.
15. PREPARATION OF CARBOXYLIC ACIDS
1. Oxidation:
A. Oxidation of primary alcohols and aldehydes
KMnO4/ H+ / Δ
K2Cr2O4 / H+
KMnO4/ H+ / Δ
K2Cr2O4 / H+
15
16. B. Oxidation of Alkylbenzene
KMnO4 / OH-
Δ / H+
Δ / H+
KMnO4 / OH-
16
17. 2. Carbonation of Grignard Reagents:
The addition of Grignard reagents to CO2 in form of dry ice gives
an acid with one more carbon more than the original Grignard
reagent.
Example:
δ-
17
18. 3. Hydrolysis of Nitriles:
Nitriles:
They are prepared by reacting a 1° or 2° alkyl halide with cyanide salt.
Acid hydrolysis of a nitriles yields a carboxylic acids.
Examples:
+ NH3
+ NH3
+ NH3
18
19. REACTIONS OF CARBOXYLIC ACIDS
1. Reaction with Bases : Salt formation
The carboxyl hydrogen is replaced by metal ion, M+
A) With strong base:
+
19
20. B) With weak base
Weaker acids like phenols react only with strong bases like
(NaOH or KOH) and will not react with NaHCO3
20
21. 2. Reaction with Nucleophiles to form acid derivatives:
When the OH of a carboxylic acid is replaced by a nucleophile, :Nu ,
a carboxylic acid derivative is produced.
21
23. NOMENCLATURE
Nomenclature: the functional derivatives’ names are derived
from the common or IUPAC names of the corresponding
carboxylic acids.
1. Esters:
Change –ic acid to –ate preceded by the alkyl is derived from the
alcohol, R'OH.
alkyl alkanoate
Examples:
23
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1. It is an effective and inexpensive topical agent to treat
human scabies.
2. It has vasodilating and spasmolytic effect in case of asthma
and whooping cough
3. It is also used an excipient in some testosterone replacement
drugs
4. It acts as Scabicide, Pediculicide and Acaricide