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CITRIC ACID
OH – C – CH2 – C – CH2 – C – OH
O║
O ║HO – C
O║
OH
CITRIC ACID
2 – hydroxy – 1,2,3 – propanetricarboxylic acid
CARBOXYLIC ACID
DEFINITION
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.
SYNTHETIC
OXIDATION of ALDEHYDE gen.
formula1ᵒ Alcohol -----→ ALDEHYDE +
H2OKMnO4
K2Cr2O7
(O)
CARBOXYLIC ACID
EXAMPLE
CH3 – CH2 – OH K2Cr2O7
(O)CH3 – C – H + H2O
O║
(O)
CH3 – C – OH
O║
ETHANOIC ACID
ETHANAL
NATURAL
H – C – OH
O║
FORMIC ACID
methanoic acid
HO – C – CH2 – C – OH
O║
O║
MALONIC/MALIC ACID
propanedioic acid
RHUBARB
HO – C – C – OH
O║
O║
OXALIC ACID
ethanedioic acid
CH3 – (CH2)18 – C – OH
O║
ARACHIDIC ACID
ICOSANOIC acid
OH – C – CH2 – C – CH2 – C – OH
OH
O ║HO – C
O║
O║
CITRIC ACID
2 – hydroxy – 1,2,3 – propanetricarboxylic acid
CH3 – (CH2)7 – CH=CH – (CH2)7 – C – OH
O║
OLEIC ACID
OLIVES
LAUREL LEAVES
CH3 – (CH2)10 – C – OH
O║
LAURIC ACID
DODECANOIC acid
Human & Animal FATS
CH3 – (CH2)16 – C – OH
O║
STEARIC ACID
OCTADECANOIC acid
USES
CH3 – C – OH
O║
ACETIC ACID
ethanoic acid
CH3 – CH – C – OH
O║
OH
LACTIC ACID
2 - hydroxypropanoi
c acid
CH3 – (CH2)2 – C – OH
O║
BUTYRIC ACID
butanoic acid
CH3 – (CH2)14 – C – OH
O║
PALMITIC ACID
hexadecanoic acid
NOMENCLATURE
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.
IUPAC RULES
Formula Common Name Source IUPAC
NameMelting 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
CH3CH2CO2Hpropionic
acidmilk (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
EXAMPLES
1009080706050403020100
Give the IUPAC & COMMON name of D’ Given Structure
CH3 – (CH2)4 – C – OH
O║
IUPAC
COMMON
HEXANOIC ACID
CAPROIC ACID
1009080706050403020100
Give the IUPAC & COMMON name of D’ Given Structure
IUPAC
COMMON
2,2 dihydroxypentanoic ACID
α,α - dihydroxyvalericACID
CH3 – (CH2)2 – C – C – OH
O║
OH
OH
1009080706050403020100
Give D’ IUPAC name of D’ CARBOXYLIC structure
HO – C – CH – C – CH – CH3
CH2 – CH3
NO2
O║
O║
IUPAC
4 – methyl – 2 – nitro – 3 – oxohexanoic ACID
1009080706050403020100
Give D’ COMMON name of D’ CARBOXYLIC structure
CH3 – (CH2)2 – C – CH – C – (CH2)2 – C – OH
NO2
CH3HO O║
O║
COMMON NAME
ε – hydroxy – δ – methyl – ε – nitro – γ – oxopelargonic acid
1009080706050403020100
Give D’ IUPAC name of D’ CARBOXYLIC structure
CH3 – (CH2)2 – C – CH2 – C – CH2 – CH3
CH2 – CH3
HO – C – 2HC (CH2)2 – CH3
CH3 – CH2
O║
IUPAC NAME
3,5,5 – triethyl – 3 – propyloctanoic acid
What if there’s a DOUBLE or TRIPLE bond in a structure?
EXAMPLES
CH3 – C ≡ C – C – OH
O║
2 – butynecarboxylic acid
O║C – OH
3 – cyclohexenecarboxylic acid
1009080706050403020100
Give D’ IUPAC name of D’ CARBOXYLIC structure
HO – C – CH – CH2 – C ≡ C – C – CH3
CH3 – (CH2)2
CH2 – CH3 O║
6 – ethyl – 6 – methyl – 2 – phenyl – 4 – nonynecarboxylic acid
1009080706050403020100
Give D’ IUPAC name of D’ CARBOXYLIC structure
CH2
O║C – OH
HO
5 – benzyl – 4 – cyclohexyl – 3 – hydroxy – 2 – cyclohexene carboxylic acid
1009080706050403020100
Give D’ IUPAC name of D’ CARBOXYLIC structure
O║C – OH
CH3 – (CH2)4
4 – pentyl – 2 – cyclopentynecarboxylic acid
1009080706050403020100
Give D’ IUPAC name of D’ CARBOXYLIC structure
CH3 – CH ═ CH – CH2 – C ≡ C – C – OH
O║
5 – hepten – 2 – ynecarboxylic acid
What if there are MULTIPLE CARBOXY in a structure?
OH – C – CH2 – CH2 – C – OH
O║
O║
butanedioic acid Succinic acid
pentanedioic acid Glutaric acid
OH – C – (CH2)3 – C – OH
O║
O║
1009080706050403020100
Give D’ IUPAC name of D’ CARBOXYLIC structure
OH – C – (CH2)4 – C – OH
O║
O║
hexanedioic acid
Adipic acid
1009080706050403020100
Give D’ IUPAC & COMMON name of D’ CARBOXYLIC structure
OH – C – CH2 – C – CH2 – C – OH
O║
O║
OH
O ║HO – C
2 – hydroxy – 1,2,3 – propanetricarboxylic acid
CITRIC ACID
1009080706050403020100
Give D’ IUPAC name of D’ CARBOXYLIC structure
O ║HO – C
O ║HO – C
O
║
HO
– C
3HC
4 – methyl – 1,2,3 – cyclobutanetricarboxylic acid
What if a CARBOXY group is bound to a benzene structure?
O ║ C – OH
benzoic acid
1009080706050403020100
Give D’ IUPAC name of D’ CARBOXYLIC structure
Cl
O ║ C – OH Br
3 – bromo – 5 - chlorobenzoic acid
1009080706050403020100
Give D’ IUPAC name of D’ CARBOXYLIC structure
O
║ C
– OH
NO2
4 – nitro – 2,6 – diphenylbenzoic acid
1009080706050403020100
Give D’ IUPAC & COMMON name of D’ CARBOXYLIC structure
OH
O ║ C – OH
2 – hydroxybenzoic acid
SALICYLIC ACID
O – hydroxybenzoic acid
1009080706050403020100
Give D’ IUPAC & COMMON name of D’ CARBOXYLIC structure
O ║ C – OH H2N
4 – aminobenzoic acid
p – aminobenzoic acid
PABA
PHYSICAL
Properties
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.
ONLY ONE OF ITS KIND
Some KINDA CarboxylicCOMMON 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 pentane 72 35 °CEther Diethyl
ether74 35 °C
Aldehyde butanal 72 76 °C
Alcohol 1 - butanol 74 118 °C
Carboxylic acid
Propanoic acid
74 141 °C
Table of Comparison
CHEMICAL
Properties
R EAC T I O N
MEC HAI S M
R E A C T I O N
N
M E C H A N I S M
A step by step description of how a chemical reaction occurs.
NO I TAZI LART U EN
N E U T R A L I Z A T I ONA reaction that involves acids and bases.
IONIZ A T I O N
I ON I Z A T I ONA reaction that deals with cations & anions.
ES T ER IF I CA T IO NA process of forming an ester.
E S T E R I F I C A T I ON
E ST E RSAn organic compound.
E S T E R S
IONIZATIONGEN. FORMULA
Carboxylic acid + Water ↔ Carboxylate ion + Hydronium ion
Example
CH3 – C – O – H + H2O
O║
Acetic acid Acetate ion
CH3 – C – O ־ + H3O +
O║hydronium ion
Ethanoate ion
Examples
O║C – O – H + H2O
O║C – O ־+ H3O +
Benzoic acid Benzoate ion
CH3 – (CH2)4 – C – O – H
O║
+ H2O
Caproic acid
CH3 – (CH2)4 – C – O ־
O║
+ H3O +
Caproate ion
hydronium ion
hydronium ion
Hexanoate ion
NEUTRALIZATIONGEN. FORMULA
Carboxylic acid + Base → Carboxylate salt + Water
Example
CH3 – C – O – H + K – OH
O║
Acetic acid
CH3 – C – O ־ K+ + H2O
O║
Potassium acetate
Potassium ethanoate
Examples
CH3 – (CH2)3 – C – O – H
O║
+ Li – OH
Valeric acid Lithium valerate
Benzoic acid
O║C – O – H + Na – OH
O║C – O ־Na++ H2O
Sodium benzoate
Lithium pentanoate
CH3 – (CH2)3 – C – O ־Li+ + H2O
O║
ESTERIFICATIONGEN. FORMULA
Carboxylic acid + Alcohol → ESTER + WaterH+/ heat
Example
CH3 – C – OH + H – O – CH3
O║
Acetic acid
H+/ heatCH3 – C – O – CH3 + H2O
O║
methyl acetatemethanol
methyl ethanoate
Example
CH3 – (CH2)2 – C – OH
O║
+ H – O – CH2 – CH3
Butanoic acid
H+/ heat
ethyl alcohol
CH3 – (CH2)2 – C – O – CH2 – CH3
O║
+ H2O
ethyl butanoate
ethyl butyrate
ExampleO║C – OH
OH
Salicylic acid
+ H – O – CH3
methyl alcohol
H+/ heat
O║C – O – CH3
OH
+ H2O
methyl salicylate
EXAMPLES
181716000102030405060708091011121314152019Do a sequence of reaction to produce methyl butyrate
an apple flavor, used in food & cosmetic industry.
CH3 – (CH2)2 – C – OH
O║
+ H – O – CH3 H+/ heat
butanoic acidmethyl alcohol
CH3 – (CH2)2 – C – O – CH3
O║
+ H2O
methyl butyratemethyl butanoate
181716000102030405060708091011121314152019Do a sequence of reaction to dissociate
ENANTHIC ACID.
CH3 – (CH2)5 – C – O – H
O║
+ H2O
enanthic acid
CH3 – (CH2)5 – C – O ־
O║
+ H3O+
enanthate ionheptanoate ion
hydronium ion
181716000102030405060708091011121314152019Do a sequence of reaction to produce Calcium propanoatea carboxylic acid salt, used commercially as preservative
in bread, cakes & cheese .
CH3 – CH2 – C – O – H
O║
propanoic acid
+ Ca – OH
Calcium hydroxide
CH3 – CH2 – C – O־ Ca+
O║
+ H2O
Calcium propanoateCalcium propionate
181716000102030405060708091011121314152019Do a sequence of reaction to produce octyl acetate
an orange flavor, used in food & pharmaceutical industry.
CH3 – C – OH
O║
+ H – O – (CH2)7 – CH3
ethanoic acid octyl alcohol
H+/ heat
CH3 – C – O – (CH2)7 – CH3
O║
+ H2O
octyl acetate octyl ethanoate
181716000102030405060708091011121314152019Do a sequence of reaction to dissociate
DECANOIC ACID.
CH3 – (CH2)8 – C – O – H
O║
+ H2O
capric acid
CH3 – (CH2)8 – C – O ־
O║
+ H3O+
caprate ion decanoate ion
hydronium ion
181716000102030405060708091011121314152019Do a sequence of reaction to produce Sodium Stearate
a long chain carboxylic acid salt, used commercially as Surfactant for Soaps .
CH3 – (CH2)16 – C – O – H
O║
+ Na – OH
stearic acidSodium hydroxide
CH3 – (CH2)16 – C – O – Na
O║
+ H2O
Sodium StearateSodium octadecanoate
What are organic compound ESTERS?
Give some examples of ESTERS?
Cite some industrial applications of ESTERS.
References: All organic chemistry book will do.
Assignments
- FIN -
