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O H O
|
H C OH H C C OH
|
H
CARBOXYL GROUP
1
Why families known as carboxylic acid
CH3COOH H+ + CH3COO-
2
Molecular and Structural Formula
Molecular Structural
n Name Mr
formula formula
O
C0H2(0)+1COOH
Methanoic
0 46
acid H C OH
= HCOOH
H O
C1H2(1)+1COOH
|
Ethanoic
1 60 H C C OH
acid = CH3COOH
|
[C2H4O2]
H
H H O
CH COOH | |
Propanoic 2 2(2)+1
2 74 H C C C OH
acid
= C2H5COOH | |
H H
3
Butanoic
3
acid
3 2 Carbon number 1
H H O
C C C
H H O H
Example 1:
4
Longest continuous chains: propanoic acid
H H
C4H8O2 / C3H7COOH
H C C COOH
H Carboxyl carbon: carbon number 1
H
Name: 2-methylpropanoic acid
Example 2:
5
Attached alkyl group: 2-methyl
CH3 C COOH
Carboxyl carbon: carbon number 1
C2H5
Example 3:
6
H
C2H5 C COOH
Example 4:
H
C3H7 C COOH
C2H5
Ethanoic Asid
Can be prepared through oxidation of an
ethanol.
7
Chemical equation:
K2Cr2O7 solutions
H H + H O
dilute H2SO4
H C C OH + 2[O] H C C OH + H2O
reflux
H H H
8
Preparation of ethanoic acid through refluxing
Tissel tube
Label the
Water out
diagram please
Liebig condenser
Water
Retort
in
stand
Rounded bottom flask
Heat
9
Physical Properties
- pH less than 7
- sharp or unpleasant smell
- turn moist blue litmus paper to red
- colourless liquid
Chemical Properties
Acid Properties
- Only hydrogen atom in the carboxyl group,
[-COOH] can ionize in water to produce
hydrogen ions, H+.
CH3COOH CH3COO- + H+
CH3COO-
Ethanoic Ethanoate Hydrogen
acid ion ion
10
Reactions with metals
- Dilute ethanoic acid reacts with reactive
metal (Zn, Mg, Al) to produce a salt and
hydrogen gas.
2CH3COOH + Mg Mg(CH3COO)2 + H2
Ethanoic acid Magnesium ethanoate
2CH3COOH + Zn Zn(CH3COO)2 + H2
Ethanoic acid Zink ethanoate
11
Reactions with bases
- Dilute ethanoic acid neutralizes alkalis such
as sodium hydroxide solution to give an
organic salt and water.
12
Reactions with carbonates
- Dilute ethanoic acid reacts with metal
carbonates to produce a salt, carbon dioxide
and water.
13
Reactions with alcohols [Esterification]
Esterification:
Concentrated
H2SO4
Carboxilic acid + Alcohol Ester + Water
14
Uses of carboxilic acid:
16
ESTER
General formula CnH2n+1COOCmH2m+1
O
CnH2n + 1C OH + CmH2m+1OH
(carboxilic acid) (alcohol)
O
CnH2n + 1C O CmH2m+1 + H2O
(ESTER)
Esterification
17
- Carboxilic acid reacts with alcohol to produce
ester and water.
- The functional group of ester is carboxilate
group.
- Concetrated sulphuric acid is catalyst.
- Carboxilic acid losses OH and
- Alcohol losses H
- The bond that break up will rejoin again
O Break up
and rejoin
CnH2n + 1 C
Derived from
carboxilic acid O CmH2m+1
Derived from
alcohol
Carboxilate
group, -COO-
Naming Ester
18
- Name of ester consists of two parts, the name
of alcohol part is given first and followed by
the acid part.
Example: i. Ethanoic acid + methanol
methyl ethanoate + water
Chemical equation:
H
H O
|
|
+ H C OH
H C C OH
|
|
H
H
CH3OH
CH3COOH
(Methanol)
(Etanoic acid)
H O H
| |
H C C O C H + H2O
| |
H H
CH3COOCH3
(Methyl ethanoat) Water
19
Example: ii. Ethanoic acid + ethanol
ethyl ethanoate + water
Chemical equation:
H O H H
| | |
H C C OH + H C C OH
| | |
H H H
H O H H
| | |
H C C O C C H + H2O
| | |
H H H
ethyl etanoat Water
20
Example: iii. Methanoic acid + Ethanol
ethyl methanoate + water
Chemical equation:
O H H
| |
H C OH + H C C OH
| |
Methanoic acid H H
Ethanol
O H H
| |
H C O C C H + H2O
| |
H H
21
Q: Draw structural molecule of
i. Methyl metanoate
ii. Pentyl propanoate
iii. Propyl ethanoate
Methyl methanoate
O H
|
H C OH H C OH
|
H
Break up and rejoin
O H
|
H C O C H + H2O
|
H
Try now
23
Prophyl ethanoate
H O H H H
| | | |
H C C OH H C C C OH
| | | |
H H H H
Break up and rejoin
H O H H H
| | | |
H C C O C C C H + H2O
| | | |
H H H H
24
Preparation of ester through reflux
Tissel tube
Liebig
condenser To cold the
Water ethanol and
out ethanoic acid
Water
in
Uniform Water
heating bath
Ethanol +
Porcelain chip ethanoic acid +
XXXXXXXXXXXXXXX
To prevent concentrated
bumping and sulphuric acid
ensure smooth
boiling
Uses of ester
27