Carboxylic Acid

Carboxylic Acid
Among important examples are :
OH H H H
COOH HOOC
NH2
NH2
COOH
Djenkolic acid Was first isolated by Van Veen and Hyman from the urine of the natives of Java who had eaten the djenkol bean and were suffering from poisoning.
H HO H H H OH
Cholic acid (a major component of human bile)
Carboxylic Acid
also, biological precursors of fats and other lipids :
HH
C
CH3(CH2)7
C
(CH2)7COOH CH3(CH2)4
C
CH2
C
(CH2)7COOH
Oleic acid
Linoleic acid
Carboxylic Acid
This compounds contain the carboxylic group attached to :
A hydrogen Alkyl group A ryl group
O and
O or
C
OH
C
OH
Ar C
OH
example
HCOOH
Formic acid
CH3COOH
Acetic acid Benzoic acid
COOH
CH3(CH2)10COOH
Lauric acid
CH2COOH
Penylic acetic acid
Carboxylic Acid
IUPAC name
Nomenclature
Carboxylic acid that are derivated from open-chain alkanes are systematically named by replacing the terminal e of the corresponding alkane with oic acid.
The carboxylic carbon atom is always numbered C1 in the system.
Propanoic acid
4-Methylpentanoic acid
3-Ethyl-6-methyloctanedioic acid
Carboxylic Acid
COMMON name
Nomenclature
To indicate the position of attachment, the Greek letters, , , , , etc are used. The -carbon is the one bearing the carboxyl group.
C-C-C-C-COOH

CH3
CH3CH2CH-COOH
- Methylbutyric acid
CH3 CH3
CH3CH2CH-CHCOOH
, -Dimethylvaleric acid
Carboxylic Acid
Physical Properties
Gugus C=O pada asam karboksilat mempunyai ikatan , sehingga dapat terjadi resonansi.
Hal yang sama tidak terjadi pada gugus OH dari alkohol.
+ Atom O pada karboksilat lebih bermuatan negatif daripada R-OH Atom H pada karboksilat lebih bersifat sebagai proton daripada R-OH
Kesimpulan Ikatan hidrogen pada karboksilat lebih kuat dari

ikatan hidrogen pada alkohol.
Carboxylic Acid
Physical Properties
2 Hydrogen bond
1 Hydrogen bond
O H3C C O H
O O
O H
CH3
O H
Still MONOMER
Acetic acid DIMER
The Fact
Boiling point of asetic acid = 118 Co Boiling point of n-Propylalcahol = 97 Co
Carboxylic Acid
Dissociation
Like other Bronsted-Lowry acids, carboxylic acid dissociate slightly in dilute aqueous solution to give H3O+ and carboxylic anion, RCOOO R C OH O
+ H2O
O-
+ H3O+
As with all acids, we can define an acidity constant, Ka:

[RCOO-][H3O+] [RCOOH]
Ka =
and
pKa = -log Ka
pKa = -7
pKa = 4,72
pKa = 16
acidity
Carboxylic Acid
Resonance Efect
CH3CH2OH
Ethanol
+ H2O
CH3CH2OUnstabilized
+ H3O+
O H3C C O H
+ H 2O
OH3C C O
H3C
O-
+ H3O+
Resonance stabilized carboxylic ion
Carboxylic Acid
Substituent Efect
STRUCTURE HCl F3CCOOH Cl3CCOOH HCOOH CH3COOH
Ka 107 0,59 0,23 1,77 x 10-4 1,8 x 10-5
pKa -7 0,23 0,64 3,75 4,72
acidity
Carboxylic Acid
1. Oxidation of primary alcohol. R-CH2OH
KMnO4
Preparation
R-COOH
CH3 CH3CH2CHCH2OH
2-Methyl-1-butanol KMnO4
CH3 CH3CH2CHCOOH
2-Methylbutanoic acid
CH3 CH3CHCH2OH
Isobutyl alcohol KMnO4
CH3 CH3CHCOOH
Isobutylic acid
Carboxylic Acid
2. Hydrolysis of Nitriles. R-C
or
Preparation
N
+ H2O
Acid or base
R-COOH
or + NH3
Ar-C CH2CN
Ar-COOH CH2COOH
70% H2SO4
Phenylacetonitrile
Phenylacetic acid
3. Carbonation of Grignard Reagents. 4. Oxydation of Alkylbenzenes. 5. Malonic Ester Syntesis.
Carboxylic Acid
R
Derivatives of
C
OH O
O R
O R
R R
C
Cl
C
OR
Ester
C
O
O R
C
NH2
Amide
Acid chloride
C
O
Anhydride
More reactive
Less reactive
Carboxylic Acid
R
H3C C O OH
Benzoic acid
Derivatives of
Nomenclature
Ar
O C OH
O C Cl
Benzoyl chloride
Acetic acid
Acid chloride
H3C C
O Cl
O
Change: -ic acid to yl chloride
Acetyl chloride
H3C C
Anhydride
O C O C O
Benzoic anhydride
O O
H3C C
Change: acid to anhydride
Acetic anhydride
Carboxylic Acid
R
H3C C O OH
O C NH2
Benzamide
Derivatives of
Nomenclature
Ar
O C OH
Benzoic acid
Acetic acid
Amide
O H3C C NH2
Change: -ic acid to amide
Acetamide
Ester
Change: acid to -ate
H3C C
O
C
O OC2H5
Ethylbenzoate
OC2H5
Ethylacetate
Carboxylic Acid
Carboxylic Acids
Derivatives of
1.Acid Chloride [an Acyl)
are converted into acid chlorides [an acyl group] by
teratment with thyonyl chloride (SOCl2), phosphorus trichloride (PCl3), or oxalyl chloride (ClCOCOCl).
O
R
O
+ SOCl2
C
OH
C
Cl
+ HCl + SO2
Carboxylic Acid
Conversion to :
H2O ROH
Derivatives of
O R C
NH3
Cl
[H]
RMgX
O R C
Acid
O OH R C
Ester
O
NH2
O
H
OR
Amide
Aldehyde
[H]
Ketone
RMgX
OH R CH H
OH R C R OR
Alcohol
t-alcohol
Carboxylic Acid
With H2 O can converted back into carboxylic acid.
O H3C C Cl
Derivatives of
HOH
H3C C
O OH
+ HCl
Acetyl chloride
Acetic acid
With alcohol can..
Cl
HOCH3
OCH3
+ HCl
Ester
Benzoyl chloride Methylbenzoate
Amide formation with amonia.
O H3C C Cl
+ 2NH3
Acetyl chloride
H3C C
NH2
+ NH4Cl
Acetamide
Carboxylic Acid
O H C O-Na+
Derivatives of
2.Acid Anhydrides
reparation :
O Cl C CH3
O H C O
O C CH3
Sodium formate
Acetyl chloride
Acetic formic anhydride
Carboxylic Acid
Conversion to :
H2O ROH
Derivatives of
O R C O
O C R
NH3 [H]
O R C
Acid
O OH R C
Ester
O
NH2
OR
H
Aldehyde
[H]
Amide
OH R CH H
Alcohol
Carboxylic Acid
In drugs industry :
H
Derivatives of
NH2 HO
p-Hydroxyaniline
O H3CC O
O CCH3
NaOH
N HO
CH3
Acetaminophen
H3CC
O-
O C OH
Salicylic acid
O
OH
O O CCH3
NaOH
C O O C
H3CC
OH
H3CC
O-
CH3
Aspirin
Carboxylic Acid
Ester is hydroxy group ini acid change into some alkyl or aryl:
The ester linkage is also present in animal fats and many biologically important molecules.
Derivatives of
3. Ester
O H2C O C R O
O CH3CH2CH2C-OCH3
Methylbutanoate [from pineaples]
CH3
HC
R O
CH3CO-CH2CH2CHCH3
Isopentyl acetate [from bananas]
H2C
A fat
Carboxylic Acid
O
Derivatives of
Conversion to :
H2O RMgX
OR
NH3
[H]
O R C
Acid
OH
OH
O
NH2
R OR
R
H
Aldehyde
[H]
t-alcohol
Amide
OH R CH H
Alcohol
Carboxylic Acid
Esters are usually prepared by the reaction of alcohols or phenols with acids or acid derivatives.
Derivatives of
ESTERIFICATION
O R
O OH + H-OR
alcohol
C
ESTER
OR
+ H-OH
Carboxylic acid
CH2OH + HOOCCH3
CH2OOCCH3
+ H-OH
Benzyl alcohol
Acetic acid
Benzyl acetat
Carboxylic Acid
Derivatives of
SAPONIFICATION
O R C
H2O
O R C
An acid
OR
NaOH
+ ROH
OH
O R C
A soap
O-Na+
Amine
Amine is derivates of ammonia, when one or more of hydrogen change into alkyl (R) or aryl (Ar).
H H
H H R
H H R
N
Ammonia
N
Primary 1o
N
Secondary 2o
N
Tertiary 3o
Amine
H3C
N N
Nicotine
O N N CH3
Caffeine
CH3
CH3
H3 C H2 C N CH2CH2OH
OH OH OH H2C H3C N C H C H N N O C H O CH2OH
N H3 C
N+
Vitamin B1
H3C
Vitamin B2
Amine
Aliphatic amine are named by naming the alkyl group or groups attached to nitrogen, and following these by the word amine.
Nomenclature
CH3 H3C C CH3
H H3CH2C N CH3
NH2
tert-Butylamine Etrhylmetylamine
Amine
Aromatic amine those in which nitrogen is attached directly to an aromatic ring, are generally named as derivatives of the simple aromatic amine, -aniline.
Nomenclature
NH2
aniline
Br
NH2 Br
H3C
C2H5
H3C
CH3
NH2
Br
2,4,6-Tribromoaniline
N-Ethyl-N-methylaniline
NO
p-Nitroso-N, N-dimethylaniline
CH3
p-Touidine
Amine
Amine are highly polar and therefore have higher boiling point than alkanes of equivalent molecular weight have, but lower boiling point than alcohol or carboxylic acids.
R R N N R R R H H N R R H N R H R N H R
Physical Properties
CPs CH3CH3 CH3NH2 CH3OH
BP (oC) -88,6 -6,3 +65,0
Mr 30 31 32
Amine
Reaction
CH3COOH
Acetic acid
Cl2
CH2COOH Cl
Chloroacetic acid
NH3
CH2COOH NH2
GLYSINE [an amino acid]
O O R R R
C
Cl
C
O
O R
O R
C
NH2
Amide
C
OR
Ester
Acid chloride
C
O
Anhydride
R-C
N HCl
O
1 2
CH2CH3
3 4 5
CH3
6 7
O
8
HOCCH2CHCH2CH2CHCH2COH CH3CH2OH

Carboxylic Acid

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Carboxylic Acid

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Carboxylic Acid

Among important examples are :

Cholic acid (a major component of human bile)

Kesimpulan Ikatan hidrogen pada karboksilat lebih kuat dari

Acetic acid DIMER

Boiling point of asetic acid = 118 Co Boiling point of n-Propylalcahol = 97 Co

As with all acids, we can define an acidity constant, Ka:

Resonance stabilized carboxylic ion

STRUCTURE HCl F3CCOOH Cl3CCOOH HCOOH CH3COOH

Ka 107 0,59 0,23 1,77 x 10-4 1,8 x 10-5

pKa -7 0,23 0,64 3,75 4,72

3. Carbonation of Grignard Reagents. 4. Oxydation of Alkylbenzenes. 5. Malonic Ester Syntesis.

Change: -ic acid to yl chloride

Change: acid to anhydride

Change: -ic acid to amide

1.Acid Chloride [an Acyl)

are converted into acid chlorides [an acyl group] by

With alcohol can..

Amide formation with amonia.

Acetic formic anhydride

OH OH OH H2C H3C N C H C H N N O C H O CH2OH

CH3 H3C C CH3

CPs CH3CH3 CH3NH2 CH3OH

BP (oC) -88,6 -6,3 +65,0

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