O
║
OH
O
║
OH – C – CH2 – C – CH2 – C – OH
O
║
HO – C
 Carboxylic
acids are organic
acids characterized by the
presence of a CARBOXYL
GROUP, which has the
formula -C(=O)OH, usually
written -COOH or -CO2H.
gen. formula
1ᵒ Alcohol -----→
ALDEHYDE + H2O
KMnO
K2Cr2O7
4
(O)
EXAMPLE
(O)
(O)
CH3 – C – OH
O
║
CH3 – CH2 – OH
K2Cr2O7
O
║
CH3 – C – H + H2O
O
║
H – C – OH
O
║
O
║
HO – C – CH2 – C – OH
O
║
O
║
HO – C – C – OH
O
║
CH3 – (CH2)18 – C – OH
O
║
OH
O
║
OH – C – CH2 – C – CH2 – C – OH
O
║
HO – C
O
║
CH3 – (CH2)7 – CH=CH – (CH2)7 – C – OH
O
║
CH3 – (CH2)10 – C – OH
O
║
CH3 – (CH2)16 – C – OH
O
║
CH3 – C – OH
O
║
CH3 – CH – C – OH
OH
O
║
CH3 – (CH2)2 – C – OH
O
║
CH3 – (CH2)14 – C – OH



A carboxylic acid is named in the IUPAC
system by replacing the –e of the alkane
name by Functional group suffix = -oic
acid.
The carboxyl carbon is designated as
number # 1, and other substituents are
located and named accordingly.
However, common names derived from
their natural source are used extensively
for most carboxylic acid, and the greek
letters alpha, beta, gamma and delta are
used to show the location of side groups.
Formula
Common
Name
Source
IUPAC
Name
Melting
Point
Boiling
Point
HCO2H
formic acid
ants (L.
formica)
methanoic
acid
8.4 ºC
101 ºC
CH3CO2H
acetic acid
vinegar (L.
acetum)
ethanoic
acid
16.6 ºC
118 ºC
CH3CH2CO2H
propionic
acid
milk (Gk.
protus prion)
propanoic
acid
-20.8 ºC
141 ºC
CH3(CH2)2CO2H
butyric acid
butter (L.
butyrum)
butanoic
acid
-5.5 ºC
164 ºC
CH3(CH2)3CO2H
valeric acid
valerian root
pentanoic
acid
-34.5 ºC
186 ºC
CH3(CH2)4CO2H
caproic
acid
goats (L. caper)
hexanoic
acid
-4.0 ºC
205 ºC
CH3(CH2)5CO2H
enanthic
acid
vines (Gk.
oenanthe)
heptanoic
acid
-7.5 ºC
223 ºC
CH3(CH2)6CO2H
caprylic
acid
goats (L. caper)
octanoic
acid
16.3 ºC
239 ºC
CH3(CH2)7CO2H
pelargonic
acid
pelargonium
(an herb)
nonanoic
acid
12.0 ºC
253 ºC
CH3(CH2)8CO2H
capric acid
goats (L. caper)
decanoic
acid
31.0 ºC
219 ºC
Give the IUPAC & COMMON name of D’ Given Structure
O
║
10
08
09
06
07
04
05
00
01
02
03
CH3 – (CH2)4 – C – OH
CAPROIC ACID
Give the IUPAC & COMMON name of D’ Given Structure
O
OH
║
10
08
09
06
07
04
05
00
01
02
03
CH3 – (CH2)2 – C – C – OH
OH
α,α - dihydroxyvalericACID
Give D’ IUPAC name of D’ CARBOXYLIC structure
10
09
08
04
05
06
07
02
03
00
01
O
║
O
║
CH2 – CH3
HO – C – CH – C – CH – CH3
NO2
10
09
08
04
05
06
07
02
03
00
01
Give D’ COMMON name of D’ CARBOXYLIC structure
HO CH3 O
║
O
║
CH3 – (CH2)2 – C – CH – C – (CH2)2 – C – OH
NO2
ε – hydroxy – δ – methyl – ε – nitro – γ – oxopelargonic acid
10
09
08
04
05
06
07
02
03
00
01
Give D’ IUPAC name of D’ CARBOXYLIC structure
CH3 – CH2
CH2 – CH3
CH3 – (CH2)2 – C – CH2 – C – CH2 – CH3
HO – C – 2HC
(CH2)2 – CH3
O
║
What if there’s a DOUBLE or TRIPLE bond in a structure?
O
║
CH3 – C ≡ C – C – OH
O
║
C – OH
10
09
08
04
05
06
07
02
03
00
01
Give D’ IUPAC name of D’ CARBOXYLIC structure
O
║
CH2 – CH3
HO – C – CH – CH2 – C ≡ C – C – CH3
CH3 – (CH2)2
10
09
08
04
05
06
07
02
03
00
01
Give D’ IUPAC name of D’ CARBOXYLIC structure
O
║
C – OH
HO
CH2
10
09
08
04
05
06
07
02
03
00
01
Give D’ IUPAC name of D’ CARBOXYLIC structure
O
║
C – OH
CH3 – (CH2)4
10
09
08
04
05
06
07
02
03
00
01
Give D’ IUPAC name of D’ CARBOXYLIC structure
O
║
CH3 – CH ═ CH – CH2 – C ≡ C – C – OH
What if there are MULTIPLE CARBOXY in a structure?
O
║
O
║
OH – C – CH2 – CH2 – C – OH
Succinic acid
OH – C – (CH2)3 – C – OH
O
║
Glutaric acid
O
║
10
09
08
04
05
06
07
02
03
00
01
Give D’ IUPAC name of D’ CARBOXYLIC structure
O
║
O
║
OH – C – (CH2)4 – C – OH
Adipic acid
10
09
08
04
05
06
07
02
03
00
01
Give D’ IUPAC & COMMON name of D’ CARBOXYLIC structure
O
║
OH
O
║
OH – C – CH2 – C – CH2 – C – OH
O
║
HO – C
10
09
08
04
05
06
07
02
03
00
01
Give D’ IUPAC name of D’ CARBOXYLIC structure
O
║
HO – C
O
║
HO – C
3HC
What if a CARBOXY group is bound to a benzene structure?
O
║
C – OH
10
09
08
04
05
06
07
02
03
00
01
Give D’ IUPAC name of D’ CARBOXYLIC structure
O
║
C – OH
Br
Cl
10
09
08
04
05
06
07
02
03
00
01
Give D’ IUPAC name of D’ CARBOXYLIC structure
NO2
10
09
08
04
05
06
07
02
03
00
01
Give D’ IUPAC & COMMON name of D’ CARBOXYLIC structure
O
║
C – OH
OH
10
09
08
04
05
06
07
02
03
00
01
Give D’ IUPAC & COMMON name of D’ CARBOXYLIC structure
H2N
O
║
C – OH






Carboxylic acids are POLAR, and form HYDROGEN
BONDS with each other.
C.A. low MW r LIQUID at room temperature w/ sharp
unpleasant ODOR.
HIGH temperatures, in vapor phase
C.A. usually exist as DIMERIC pairs.
LOWER C.A.(1 to 4 carbons) are MISCIBLE with
water, whereas HIGHER carboxylic acids are very
much less-soluble due to the increasing
HYDROPHOBIC nature of the alkyl chain.
They tend to be rather SOLUBLE in less-polar
solvents such as ETHERS and ALCOHOLS.
COMMON
BOILING °C
MELTING °C
SOLUBILITY
Formic acid
101
8
infinite
Acetic acid
118
17
Infinite
Propionic acid
141
- 21
infinite
Butyric acid
164
-5
infinite
Valeric acid
186
- 34
5
Caproic acid
205
-3
1
Caprylic acid
239
17
insoluble
Capric acid
270
32
insoluble
Lauric acid
299
44
insoluble
Myristic acid
decomposes
58
insoluble
Palmitic acid
decomposes
63
insoluble
Stearic acid
decomposes
71
insoluble
CLASS
COMPOUND
WEIGHT
BOILING
Alkane
Ether
72
74
35 °C
35 °C
Aldehyde
pentane
Diethyl
ether
butanal
72
76 °C
Alcohol
1 - butanol
74
118 °C
Carboxylic
acid
Propanoic
acid
74
141 °C
A step by step description of how a chemical reaction occurs.
R E A C T I O N
ME CHAN I S M
A reaction that involves acids and bases.
NE U T R A L I Z A T I ON
A reaction that deals with cations & anions.
I ON I Z A T I ON
A process of forming an ester.
E S T E R I F I C A T I ON
An organic compound.
E
S
T
E R
S
Carboxylic acid + Water
O
║
CH3 – C – O – H + H2O
↔
Carboxylate ion + Hydronium ion
O
║
CH3 – C – O ‫־‬
+ H 3O +
O
║
C – O – H + H 2O
O
║
C – O ‫־‬+ H3O +
O
║
CH3 – (CH2)4 – C – O – H + H2O
O
║
CH3 – (CH2)4 – C – O ‫ ־‬+ H3O +
Carboxylic acid + Base
O
║
CH3 – C – O – H + K – OH
→
Carboxylate salt + Water
O
║
CH3 – C – O ‫ ־‬K+ + H2O
O
║
CH3 – (CH2)3 – C – O – H + Li – OH
O
║
CH3 – (CH2)3 – C – O ‫־‬Li+ + H2O
O
║
C – O – H + Na – OH
O
║
C – O ‫־‬Na+ + H2O
→
H+/ heat
Carboxylic acid + Alcohol
O
║
CH3 – C – OH + H – O – CH3
H+/ heat
ESTER + Water
O
║
CH3 – C – O – CH3 + H2O
O
║
CH3 – (CH2)2 – C – OH
H+/ heat
+ H – O – CH2 – CH3
O
║
CH3 – (CH2)2 – C – O – CH2 – CH3 +
H2 O
O
║
C – OH
H+/ heat
+ H – O – CH3
OH
O
║
C – O – CH3
+
OH
H2O
Do a sequence of reaction to produce methyl butyrate
an apple flavor, used in food & cosmetic industry.
O
║
CH3 – (CH2)2 – C – OH + H – O – CH3
O
║
CH3 – (CH2)2 – C – O – CH3
+
H+/ heat
H2O
Do a sequence of reaction to dissociate
ENANTHIC ACID.
O
║
CH3 – (CH2)5 – C – O – H + H2O
O
║
CH3 – (CH2)5 – C – O ‫ ־‬+
H3O+
Do a sequence of reaction to produce Calcium propanoate
a carboxylic acid salt, used commercially as preservative
in bread, cakes & cheese .
O
║
CH3 – CH2 – C – O – H
+ Ca – OH
O
║
CH3 – CH2 – C – O‫ ־‬Ca+ +
H2O
Do a sequence of reaction to produce octyl acetate
an orange flavor, used in food & pharmaceutical
industry.
O
║
CH3 – C – OH + H – O – (CH2)7 – CH3
O
║
CH3 – C – O – (CH2)7 – CH3 +
H2O
H+/ heat
Do a sequence of reaction to dissociate
DECANOIC ACID.
O
║
CH3 – (CH2)8 – C – O – H + H2O
O
║
CH3 – (CH2)8 – C – O ‫־‬
+
H3O+
Do a sequence of reaction to produce Sodium Stearate
a long chain carboxylic acid salt, used commercially as
Surfactant for Soaps .
O
║
CH3 – (CH2)16 – C – O – H + Na – OH
O
║
CH3 – (CH2)16 – C – O – Na
+
H2O




What are organic compound
ESTERS?
Give some examples of ESTERS?
Cite some industrial applications of
ESTERS.
References: All organic chemistry
book will do.