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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
Butanoic
3
acid
3
Naming carboxilic acids
3 2 Carbon number 1
H H O
C C C
H H O H
Example 1:
Longest continuous chains: propanoic acid
H H
C4H8O2 / C3H7COOH
H C C COOH
H Carboxyl carbon: carbon number 1
H
Name: 2-methylpropanoic acid
4
Example 2:
Attached alkyl group: 2-methyl
C2H5
5
Example 3:
H
C2H5 C COOH
C3H7
Example 4:
H
C3H7 C COOH
C2H5
6
Ethanoic Asid
Can be prepared through oxidation of an
ethanol.
Chemical equation:
K2Cr2O7 solutions
H H + H O
│ │ dilute H2SO4 │ ║
H — C — C — OH H — C — C — OH + H O
+ 2[O] 2
│ │ reflux │
H H H
7
Preparation of ethanoic acid through refluxing
Tissel tube
Liebig condenser
Retort Water
stand in
Rounded bottom flask
Heat
8
Physical Properties
- pH less than 7
- sharp or unpleasant or sour smell
- turn moist/damp 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+.
CH3COO- + H+
CH3COOH CH3COO-
Ethanoic Ethanoate Hydrogen
acid ion ion
9
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
10
Reactions with bases (5.2)
- Dilute ethanoic acid neutralizes alkalis such
as sodium hydroxide solution to give an
organic salt and water.
11
Reactions with carbonates
- Dilute ethanoic acid reacts with metal
carbonates to produce a salt, carbon dioxide
and water.
12
Reactions with alcohols [Esterification]
Esterification:
Concentrated
H2SO4
Carboxilic acid + Alcohol ———→ Ester + Water
13
Uses of carboxilic acid:
14
Conclusion on chemical reaction;
2. Effective Practise pg 75
1, 2, 3
[exercise book]
15
ESTER
General formula CnH2n+1COOCmH2m+1
O
║
CnH2n + 1C — OH + CmH2m+1OH
(carboxilic acid) (alcohol)
O
║
CnH2n + 1C — O — CmH2m+1 + H2O
(ESTER)
16
Esterification
- Carboxilic acid reacts with alcohol to produce
ester and water.
- The functional group of ester is carboxyl
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-
17
Naming Ester
- 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:
18
H
H O |
| ║ H— C — O-H
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
H H
H O | |
| ║ H— C — C — O-H
H — C — C —OH + | |
| H H
H
Ethanol
Ethanoic acid
H O H H
| ║ | |
H — C — C — O — C — C — H + H2O
| | |
H H H
ethyl etanoat Water
20
H H
| |
O H— C — C — O
║ + | |
H—C— H H
Methanoic acid Ethanol
O H H
║ | |
H — C — O — C — C — H + H2O
| |
H H
Try now
22
23
Prophyl ethanoate
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
Water ethanoic acid
in
Uniform Water
heating bath
Ethanol +
Porcelain chip ethanoic acid +
XXXXXXXXXXXXXXX
To prevent concentrated
jumping/efferve sulphuric acid
scent and ensure
smooth boiling
25
Physical properties of ethyl ethanoate
- colourless
- fragrant / pleasant smell
- insoluble in water
- lese dense in water
- neutral compound
Natural Sources
- Most simple esters are found in fruits and
flowers.
ex: benzyl ethanoate in Jasmine
ethyl butanoate in pineapple
Exercise:
Effective Practise pg 84 no. 1-3
[Ex. Books]
Prepared by;
Kamal Ariffin Bin Saaim
SMKDBL
http://kemhawk.webs.com
27