Beruflich Dokumente
Kultur Dokumente
Chapter 10
Nomenclature of
Carboxylic Acids
The longest chain must contain the
carboxyl group.
The carboxyl group is at the terminal,
therefore the carbon of the carboxyl group
is not numbered.
One COOH carboxyl group is at one end
Two COOH carboxyl groups are at both
ends
Name the compound as alkane, drop e
in alkane and add oic acid (eg:
CH3
Br
CH3
CH
CH
O
CH2 C
OH
4-bromo-3-methylpentanoic acid
If, two COOH groups, the compound will be
named as alkanedioic acid
HO
OH
pentanedioic acid
1.
HO
2.
HO
3.
CH3
C CH2 CH
COOH
CH
CH
CH3
COOH
COOH
4.
CH3
5.
Br
CH3
COOH
COOH
6.
Cl
7.
COOH
Odour
lower aliphatic carboxylic acid-pungent
eg : ethanoic acid (vinegar)
unpleasant odours as chain gets larger
eg : butanoic (perspiration)
pentanoic acid (rancid acid)
hexanoic acid (vomit)
Taste
Sour
Boiling Point
The boiling point of carboxylic acid is higher than an alcohol,
a ketone or an aldehyde (with Mr that almost the same)
because:
i.
ii.
iii.
Hydrogen bond
O
R
O
C
C
O
O
Hydrogen bond
Solubility
Solubility in water
Carboxylic acids are soluble in water due to
the formation of hydrogen bond between the
water molecules and carboxylic acid
molecules.
Hydrogen Bonds
O
R
H
O
C
O
C
H
Oxidation
O
R
O
+ NaOH
+ H2 O
-
O Na+
OH
COO
COOH
+ NaOH
+ H2 O
O
R
C OH
C O M
H2
O
R
C OH
C Cl + SO2 + HCl
O
PCl5
C Cl + POCl3 + HCl
5. Esterification
O
OH + HOR
carboxylic acid
alcohol
H+
C
ester
O R' + H2O
C OH + HO C
heat
R C
C R + H2 O
acid anhydride
O
O
R
C OH
RNH2
(1o amine)
NHR + H2O
2o amide
O
R2NH
(2 amine)
o
NR2 + H2O
(3o amide)
8. Reduction
R'
Ni / H2
180C
R CH2 OH
1o alcohol
Este
rs
Nomenclature of
Ester
Esters are named
by first naming the group that came
from the alcohol.
This word is followed by a space and then the name
of the acid is changed by
dropping the -oic acid ending of the parent acid and
adding -oate.
Ethyl ethanoate
Esters have same molecular formula as carboxylic
acids but are neutral compounds
phenyl ethanoate
4. methyl benzoate
Physical
Properties
Example
Boiling point
Ester
Methyl
methanoate
31.5 C
Carboxylic acid
Ethanoic acid
117.9 C
Hydrolysis of Esters
Ester hydrolysis
Alkaline
hydrolysis
Acid
Hydrolysis
Acid + alcohol
Hydrogenatio
n of oils
Soaps
Soaps are saponification / alkaline hydrolysis of ester
(Soap can be obtained through the reaction of alkaline hydrolysis of ester)
Example of soaps
sodium stearate
sodium palmitate
NaC17H35COO
NaC17H31COO
O
C
nonpolar
O
polar
Detergents
Na5P3O10 + 5 H2O