Alok sr. sec.
school
Hiran magri, sector-11 udaipur
Session 2019-2020
A chemistry project
Submitted to:-
Central board of secondary education
Under guidence submitted by
Mr.siddarth choudary shivani damor
Alok senior secondary school
Hiran Magri sector-11, udaipur(raj)
Session 2019-2020
CERTIFICATE
It is certify that project works that follows in writing is genuine
work done by shivani damor (roll no.________)of class XII Science. It
is complete in all forms to the C.B.S.E of year 2019-2020.
The following report has been completed with approval of the
school and with the full satisfaction of the teacher as well as no
part of it has been submitted in any other examination before.
Mr.siddarth choudhary MR.Shashank Taunk
(H.O.D CHEMISTRY) (PRINCIPAL)
ALOK SENOIR SECONDARY SCHOOL
Hiran magri, sector 11 , UDAIPUR (RAJ)
SESSION 2019 - 2020
ACKNOWLEDGEMENT
Thank you lord making me on instrument to make this
project report. I would like to thank all those who
have acted as real support to make this report. In
this series first of all I would like to thank my
family members without their motivation it wouldn’t be
possible for me to do it.
I would Also like to thank Mr.siddharth choudhary for
guiding me in all presentational aspect of project
report. I would like to thank our director sir,our
beloved principal and all my teacher for your inspiring
word.I would also like to thank my friend for making me
comfortable to make report.
Presented by
Shivani damor
(Roll no. _______)
Class- XII B
PROJECT TOPIC
STUDY ABOUT
‘‘CARBOXYLIC ACID’’
TABLE OF
CONTENTS
Contents
page no.
Front page I
Certificate II
Acknowledgement III
Project topic IV
1.intoduction 1
2. natural carboxylic acid 1
3.nomenclature of caroxylic acid 2
4.common name of carboxylic acid 3
5.systematic nomenclature of substituted carboxylic acid
6.properties of carboxylic acid
7. Carboxylation of Grignard reagent
8. Reaction of carboxylic acid
Reaction with sodium bicarbonate
Reaction with strong base
Reaction with diazomethane
Reaction with amines
Carboxylic acid
Introduction
Carboxylic acid are organic compound containing the carboxyl group (-
COOH), wherein the hydroxyl group (-OH) is directly attached to the
carbonyl (C=O) group.
Carboxylic acid constitutes one of the most frequently encountered
classes of organic compound in nature.
Natural carboxylic acids
A great many carboxylic acid are encountered in nature, mostly in fruit.
Indeed carboxylic acid were among the first class of organic compound
to ever be isolated from nature.
Lactic acid
Citric acid
Edible carboxylic acid found in citrus fruits and fermented milk
generally has sharp flavors.
Nomenclature of carboxylic acid
The common names of same basic carboxylic acids are derived from
Latin names that indicate the first original natural source of the
carboxylic acid.
Structure of acid Natural Common name
source
H-COOH Ants (Formica) Formic acid
CH3-COOH Vinegar (acetum) Acetic acid
CH3CH2-COOH Basic fat (propio) Propionic acid
CH3CH2CH2-COOH Rancid butter Butyric acid
(butyrum)
CH3CH2CH2CH2-COOH Valerian herb Valeric acid
CH3CH2CH2CH2CH2-COOH Goat (caper) Caproic acid
Common name of carboxylic acids
The common name of a carboxylic acid (R-COOH)is derived by
adding the suffix –ic acid to a prefix representing the chain length
of the carboxylic acid.
# of carbon Prefix Common name of acid
1 Form- Formic acid
2 Acet- Acetic acid
3 Propion- Propionic acid
4 Butyr- Butyric acid
5 Valer- Valeric acid
6 Capro- Caproic acid
Aromatic acid Benzo- Benzoic acid
IUPAC nomenclature of aliphatic
carboxylic acid
IUPAC name of straight chain aliphatic acid are derived by adding
the suffix –oic acid to the systematic name of the parent
hydrocarbon. They are named as alkanoic acids.
Systematic nomenclature of
substituted carboxylic acid
The systematic names of substituted aliphatic carboxylic acids are
derived by:
1. First identifying the parent chain that contains most, if not all
the carboxyl group.
2. Number the parent chain that contain most ,if not group i.e.
the carboxyl carbon is C-1
3. Identify the substituent and assign each substituent a
locator/address number consistent with the numbering in
the parent chain.
4. Arrange the name of substituent in alphabetical order in the
systematic name of the poly-substituted carboxylic acid
Substituted aromatic carboxylic acid
Substituted aromatic acids with one carboxyl group are
named as derivatives of benzoic acid , with the position of
substituent being cited using the locator according to their
position on the benzene ring relative to the carboxyl group.
The carbon on which the carboxyl group is attached is by
convention C-1.
PROPERTIES OF CARBOXYLIC ACID
The physical properties of carboxylic acid can be explained from
the perspective of the bond polarization in the carboxyl group and
its capacity to engage in hydrogen – bonding. Carboxylic acid boils
at considerably higher temperature than alcohol, ketone, or
aldehydes of similar molecular weight.
1]. Solubility
Carboxylic acid is polar. Because they are both hydrogen – bond
acceptor and hydrogen bond donor, they also participate in
hydrogen bonding. Carboxylic usually exist as dimer in nonpolar
media due to their tendency to ‘ self associate’ . smaller carboxylic
acids are soluble in water , whereas higher carboxylic acid have
limited solubility due to the increasing 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 tendency to form
stabilized dimmers through hydrogen bond. For boiling to occur ,
either the dimer bonds must be broken or either dimer
arrangement must be vaporized , increasing the enthalpy of
vaporization requirements significantly.
[3]. Acidity
Carboxylic acids are bronsted – Lowry acids because they are
proton donor. They are the most common type of organic acid.
Carboxylic acids are typically weak acid, meaning that 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 over the two oxygen atom increasing the 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
preparation of the perfumes
[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 main component of lipids and polyamides of 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 important carboxylic acids include acetic acid
(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
acid (food preservatives), important carboxylate salts are soaps.
Carboxylation of Grignard reagent
both aliphatic and aromatic carboxylic acids cn be prepared by
carboxylation of Grignard reagent
Reaction of carboxylic acids
1. Reaction of carboxylic acid with sodium
bicarbonate
Most carboxylic acid are stronger acid than carbonic acid (H2CO3).
They displace carbonic acid form its salts. the most reliable test for
carboxylic acid employs NaHCO3 leading to evolution of CO2.this is
commonly called the bicarbonate test foe carboxylic acids.
2. Reaction of carboxylic acid with strong base
R-C-O-H + NaOH R-C-O + H2O
Bases such as metal hydroxides (NaOH and KOH ) and amines abstract
the acidic proton on carboxylic acid to form carboxylate salts.
Mechanism:
Example:
3.Reaction of carboxylic acid with diazomethane
Diazomethane reacts rapidly with carboxylic acid to provide methyl
esters .
R-C-OH + CH2N2 R-C-OCH3 + N N
Diazomethane
Example:
4.Reaction of carboxylic acid with amines
Amines , being organic bases , react with carboxylic acid to form
ammonium salt.
Mechanism:
Example:
Mechanism of coupling carboxylic acid with amines
using DCC
The DCC serve to activate the hydroxyl group attached to the
carbonyl of the carboxyl group , thus converting it to a good
leaving group.
5. Reaction of carboxylic acid with phosphorus
pentachloride
Carboxylic acids react with phosphorus pentachloride to provide acid
chloride
The success of the reaction depends on the strength of the P=O Bond
that is formed in phosphorus oxytrichloride.
Example:
6. Reduction of carboxylic acid to primary
alcohol
Carboxylic acids are reduced to primary alcohol when treated with a
strong reducing agent such as LiAIH4.
R-CO2H R CH2OH
Example:
Medium strength reducing agent such as sodium borohydride that
reduce aldehyde and ketone are not sufficiently strong to reduce
carboxylic acid.
