The document provides a comprehensive overview of carboxylic acids, covering their introduction, structure, nomenclature, preparations, physical and chemical properties, and pharmaceutical uses. It details methods for synthesizing carboxylic acids and their derivatives, such as esters, amides, and acyl chlorides, including various chemical reactions involved in these processes. Additionally, it discusses the applications of specific carboxylic acids, like formic and acetic acids, in industrial and pharmaceutical contexts.

3. CONTENT ;
TNTRODUCTION
STRUCTURE
NOMEMCLATURE
PREPARATIONS
PHYSICAL PROPERTIES
CHEMICAL PROPERTIES
PHARMACEUTICAL USES

5. INTRODUCTION
Organic compounds which contain
CAROXLY GROUP (_COOH).
Name CARBOXYL → CARBonyl
(_C=O) & hydrOXYL (_OH) because in
carboxyl group these 2 groups are
directly bonded to each other .

6. STRUCTURE ;
They are represented (GENERAL STRUCTURE
FORMULA)as:
CARBONYL GROUP O
║ HYDROXYLIC GROUP
R—C—OHR may be H or ALKYL group

7.  Because of HYDROGEN in the _COOH group.
 Recall that acids are compound gives H+ ions in solution.
 Carboxylic acid in solution dissociate into following ions :
 REACTION;

8. NOMENCLATURE ;
Two system for naming:
1.Trivial names.
2.IUPAC names.

9. TRIVIAL NAMES
 Derived from Latin & Greek words → indicate their natural origin .
 Example;
 Formic acid(HCOOH)→Latin word →formic → ANT → secreted by ant.
 Acetic acid (CH3COOH) → Latin word → Acetum →Vinegar →present in vinegar.
 In the common system, position of subsitutants on the chain are labeled with
Greek letters.

10. EXAMPLES

11. IUPAC Names
 Name by replacing –e of the corresponding alkanes name with –oic acid.
 -COOH carbon atom is number C1.
 Compound having multi _COOH group, add di or tri to suffix _oic acid
 EXAMPLES;
pentanoic acid

12. PREPARATIONS OF CARBOXYLICACIDS
OXIDATION OF ;
ALKYL BENZENE.
UNSATURATED HYDROCARBON.
1°ALCOHOLS & ALDEHYDES.
CARBOXYLATION OF GRIGNARD REAGENT.
HYDROLYSIS OF NITRILE.
HYDROLYSIS OF ESTER.
CARBOXYLATION OF ALKENE .

13. OXIDATION OF ALKYL BENZENE
 When aliphatic side –chain at benzene ring subjected to oxidation with
alkaline KMnO4 ,gives aromatic carboxylic acids.
 REACTION;

14. OXIDATION OF ALKENES;
 In the oxidation of UNSATURATED HYDROCARBONS with alkaline
permanganate, yield a carboxylic acid.
 Not very useful for synthesis purposes → poor yield & mixture of acids
 Oxidative cleavage of unsaturated hydrocarbon → locate position of unsaturation
in molecules .
 REACTION;

15. OXIDATION OF 1° ALCOHOLS &ALDEHYDES
 Carboxylic acids are also prepared by oxidation of pri alcohol & aldehydes with
alkaline KMnO4 OR acidic K2Cr2O7.
 PRI Alcohol → Aldehyde → Carboxylic acid
 REACTION;

16. CARBOXYLATIONOF GRIGNARDREAGENT
 Grignard reagent react with CO2 to from addition products →hydrolyzed to
carboxylic acids .
 REACTION;

17. HYDROLYSIS OF NITRILES
 Nitrile is treated with hot H2O →HYDROLYSIS→ Carboxylic acids &
ammonium.
 REACTION;

18. HYDROLYSIS OF ESTERS
 Esters are boiled with conc. Aq. NaOH, Na salts of an acids
are formed which on treating with dil. HCL gives
corresponding carboxylic acids.
 REACTION;

19. PHYSICAL PROPERTIES OF CARBOXYLIC ACIDS
 Odour
 Have strong odours, especially those that are volatile. Common odours can be
found in vinegar, which contains ethanoic acids.
 Boiling point;
 Have High boiling points as;
Formula Common
Name
Source IUPAC Name Melting Point Boiling Point
HCO2
H formic acid ants (L.
formica)
methanoic
acid
8.4 ºC 101 ºC
CH3
CO2
H acetic acid vinegar (L.
acetum)
ethanoic acid 16.6 ºC 118 ºC
CH3
CH2
CO2
H propionic acid milk (Gk.
protus prion)
propanoic acid -20.8 ºC 141 ºC

20. CONTD
 REASON → H-bonding b/w 2 molecules → DIMERS→ ↑ the strength of
the van der Waals dispersion forces → high boiling points of carboxylic
acids.
 Melting point;
follow saw-tooth rule →irregular increase of M.P.
 Carboxylic acids are weak acids.
 Are polar →solubility ↓ as no. of carbon atoms of carboxylic acids↑
.

21. CHEMICAL PROPERTIES OF CARBOXYLICACIDS
SALT FORMATION.
NUCLEOPHILIC ACYL SUBSTITUTION.
REDUCTION.
a- Halogenations.
Hunsdiecker reaction.

22. SALT FORMATION
 Carboxylic acids react with NaOH , Na2CO3 and NaHCO3 to form corresponding
salts
 REACTION;

23. NUCLEOPHILIC ACYL SUBSTITUTION.
Nucleophilic attack at CARBONYL group by
SOCL2,another carboxylic mol., RCOH & NH3
Replacement of OH of carboxylic group by Cl
,OCOR ,OR & NH2.
To Forms acid chlorides, acid anhydrides,
esters & amides respectively .

24. NUCLEOPHILICACYLSUBSTITUTION.

25. REDUCTION
 Undergo reduction with lithium aluminium hydride to yield pri. Alcohols.
 Not reduced with H2 /Ni .
 REACTION;

26. a- Halogenations
 Acids having a hydrogen is treated with Cl 2/Br2 in presence of phosphorus, a
hydrogen replaced by Cl / Br..
 Also called HELL-VOLHARD-ZELINSY (HVZ)REACTION.
 REACTION;

27. Hunsdiecker reaction
 In a Hunsdiecker reaction, the silver salt of an aromatic carboxylic acid is
converted by bromine treatment to an acyl halide.
 REACTION;

29. FORMIC ACID
Used in ;
 Textile dyeing & finishing.
 As coagulating agent for rubber
latex.
 In laboratory preparation of carbon
molecules.
 As an antiseptic uses.
 In cure of gout .

30. CONTD
ACETIC ACIDS
Used in manufacturing of ;
 White vinegar
 Cellulose acetate ,polyvinyl acetate
 Acetone and esters are used in perfumes, dyes , plastics.
 used as preservative e.g.; in pickle

31. CONTD
n-BUTYRIC ACIDS
Used in the tanning industry for deliming of hide
 GABA (GAMMA-AMINOBUTYRIC ACID) is used for
calm and relaxation.
Structural
formula of n-
Butyric acid

32. Others uses
As drugs, such as
ASPIRIN
Manufacturing of soap.
For production of soft
drinks , food production.

33. DERIVATIVES OF CARBOXYLIC ACIDS
ESTERS.
AMIDES.
ACYL CHORIDES.
ACID ANHYDRIDES.

35. TNTRODUCTION
The word 'ester' was coined in 1848 by a
German chemist Leopold Gmelin, probably as a
contraction of the German Essigäther, "acetic
ether".
Chemical compound derived from an acid
(organic or inorganic) in which at least one –OH
(hydroxyl) group is replaced by an –O–alkyl
(alkoxy) group.
CARBOXYLIC ACIDS + ALCOHOL→ESTERS

36. STRUCTURE
 Generally written as ‘RCOOR’ or RCO2R’.
 Structure formula as follow;

37. NOMENCLATURE ;
Two system for naming:
1.Trivial names.
2.IUPAC names.

38. TRIVIAL NAMES
 Named from common name of acid used to form them.
 Drop “_oic acid” from common acid named and add suffix
“_ate”.
 The other carbon group is named as a substitution .

39. IUPAC NAMES
 According to IUPAC system the ALCOHOLIC PART of ester
is named First.
 This following by name of acid when the “_ic “ ending of acid
has been changed “_oate”.

40. IUPAC NAMES

41. EXAMPLES

42. PREPARATIONS OF ESTERS
FROM CARBOXYLIC ACID
FROM ACYL CHLORIDES
FROM ACID ANHYDRIDES
FROM DIAZOMETHANE
TRANS-ESTERIFICATION
FROM CARBOXYLIC SALTS & ALKYL
HALIDES

43. FROMCARBOXYLIC ACID
oESTERIFICATION
 Also known as “FISCHER ESTERIFICATION”.
 Refluxing a mixture of a carboxylic acid and an alcohol in the
presence of acid catalyst “conc. Sulphuric acid”
 Reversible & slow reaction.
 General Reaction:

44. EXAMPLE

45. FROM ACYL CHLORIDES
 Also prepared by the reaction of acid chlorides with alcohols .
 Acid chlorides →more reactive toward Nucleophilic substitution reaction → occur
rapidly.
 Does not require a catalyst.
 Pyridine is used to react with HCL that is formed in the reaction.

46. From acid anhydrides;
 Prepared from acid anhydrides by their reaction with alcohol.
 No catalyst is required.But still Required heating.
 The reaction is slower than reaction with acyl chlorides.
 General Reaction

47. Fromcarboxylic salts & Alkyl halides
Esters are formed when carboxylic salts react with Alkyl halides.
O O
║ _ ║
R—C—ONa + XR R—C—OR + NaX
+
→CARBOXYLIC SALT
• ALKYL HALIDES
ESTER

48. From Diazomethane
Methyl esters can be prepared by the reaction of
carboxylic acid with Diazomethane in etheral
solution .

49. Trans-esterification
 Hydrolysis of esters involves a Nucleophilic displacement of alcohol.
 The reaction is called ALCOHOLYSiS , analogous to hydrolysis.
 Alcohol behave as Nucleophilic.
 Catalyst by strong acids, such as conc.H2SO4 or dry HCL.
 Reaction is reversible
conc.H2SO4 or dry HCL

50. Reactions of esters
CONVERSION OF ESTER ONTO CARBOXYLIC ACID
→HYDROLSIS
CONVERSION OF ESTER INTO AMIDE
→AMMONOLYSIS
CONVERSION OF ESTERS INTO ALCOHOL
→REDUCTION
→FROM GRIGNARD REACTION
TRANS-ESTERIFICATION

51. Hydrolysis
An ester is hydrolyzed slowly → carboxylic
acid and an alcohol on heating with water.
However, hydrolysis can be catalyzed by
either a strong acid ,mineral acid ,or a strong
alkali ,such as NaOH.

52. CONTD;
 Acid-catalysed hydrolysis
 Esters when heated with water in the presence of acid catalyst (H2SO4 or HCL)
gives parent carboxylic acid and alcohol.
 The acid- catalysed hydrolysis of ester is reversible.
 Ester hydrolysis is favoured in dilute acid.

53. CONTD;
Alkaline hydrolysis
The alkaline hydrolysis of esters is usually called
“Saponification”(soap making) because the similar salts of
long-chain fatty acids have properties of soaps.
Refluxing an ester with a strong alkali,such as sodium or
potassium hydroxide,gives salts of carboxylic acid and alcohol.

54. Ammonolysis.
 Esters react slowly with ammonia to yield
amides.
 Reaction involves Nucleophilic attack by
ammonia on the electron-deficient acyl carbon
,to replace the alkoxyl group of the ester.

55. Chemical reduction
Esters also reduced by the use of Na metal and alcohol or more
commonly by the use of LiAlH4 in etheral solution.
REACTION;
.
REDUCTION OF ESTERS

56. From Grignard reagents
Esters react with Grignard reagents to form tertiary
alcohols having two Alkyl group deriVed from the
Grignard reagents ,and one from the acyl group of
the ester.

57. Trans-esterification
 Hydrolysis of esters involves a Nucleophilic displacement of alcohol.
 The reaction is called ALCOHOLYSiS , analogous to hydrolysis.
 Alcohol behave as Nucleophilic.
 Catalyst by strong acids, such as conc.H2SO4 or dry HCL.
 Reaction is reversible
conc.H2SO4 or dry HCL

59. ETHYL ACETATE
 Used as
 A solvent in industry.
 For resins.
 In artificial fruit flavors.
 In organic synthesis, for making ethyl acetoacetate.

60. Ethyl propionate
 Used in ;
 perfumery and fragrance.
 to manufacture various propionates which used in
the reduction of pharmaceuticals,
 anti-fungal agents, agrochemicals, plastics, rubber
chemicals, dyes, artificial flavors and perfumery
synthetics.

61. glyceryl trinitrate
(Nitrate esters)
Medication used for heart
failure, high blood
pressure, and to treat and
prevent chest pain from not
enough blood flow to the
heart (angina) or due to
cocaine.

62. Reference;
Text book of organic chemistry by Bs.Bhal.
Text book of organic chemistry by M.Younas.
Punjab text book of Organic for fsc 2nd year.