CARBOXILIC ACID

General formula CnH2n+1COOH

One hydrogen atom is replaced with functional
group COOH

Formula: HCOOH

H C OH

Formula: CH3COOH

H
O
|

H C C OH
|
H

CARBOXYL GROUP

Why families known as carboxylic acid

Carboxyl group plays a vital role to gives

acidic properties to carboxilic acid families.
CH3COOH
Ethanoic
acid

H+ + CH3COOHydrogen Ethanoate
ion
ion

Molecular and Structural Formula

n

Name

Methanoic
acid

Molecular
formula

Mr

C0H2(0)+1COOH
= HCOOH

C1H2(1)+1COOH
1

Ethanoic
acid
= CH3COOH
[C2H4O2]

Structural
formula

46
H C OH

H O
|

60 H C C OH
|
H

H H
O
CH
COOH
|
|

Propanoic 2 2(2)+1
74 H C C C OH
acid
= C2H5COOH
|
|
H H

Butanoic
acid
3

Naming carboxilic acids

3

Carbon number 1

O
C
O

Example 1:
H
H

Longest continuous chains: propanoic acid

H
C

COOH

H
H

C4H8O2 / C3H7COOH

Carboxyl carbon: carbon number 1

C H

Attached alkyl group: 2-methyl

H
Name: 2-methylpropanoic acid
4

Example 2:
Attached alkyl group: 2-methyl
Longest continuous chains: butanoic acid

H
CH3

COOH
Carboxyl carbon: carbon number 1

C2H5
Name: 2-methylbutanoic acid

Example 3:
H
C2H5

COOH
Name: 2-ethyl pentanoic acid

C3H7
Example 4:
H
C3H7

COOH
Name: 2-ethyl pentanoic acid

C2H5

Ethanoic Asid
Can be prepared through oxidation of an
ethanol.
Chemical equation:
CH3CH2OH + 2[O] CH3COOH + H2O
Etanol
ethanoic acid

H H

H C C OH + 2[O]

K2Cr2O7 solutions
+
dilute H2SO4
reflux

H O

H C C OH + H2O

This is carried out by refluxing ethanol with

an oxidising agent such as acidified potassium
dichromate(VI) or potassium manganate(VII)
solution.

Preparation of ethanoic acid through refluxing

Tissel tube
Water out

Retort
stand

Label the
diagram please

Liebig condenser

Water
in

Rounded bottom flask

Wire
gauge

xxxxxxxxxxxxxx

Absolute ethanol, C2H5OH +

Acidified potassium dichromate(VI),
K2Cr2O7 solution

Heat

Condenser is used to prevent the loss of a

volatile liquid by vaporisation.
This method of retaining a volatile liquid
during heating is called refluxing.
How to carry out the activity?
8

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+
CH3COOEthanoate Hydrogen
ion
ion

Ethanoic
acid

Ethanoic acid is a weak acid. Why?

- it dissociates in water partially, most of
the molecules remain unchanged.
9

Reactions with metals

- Dilute ethanoic acid reacts with reactive
metal (Zn, Mg, Al) to produce a salt and
hydrogen gas.
2CH3COOH + Mg
Ethanoic acid

Mg(CH3COO)2 + H2
Magnesium ethanoate

2CH3COOH + Zn
Ethanoic acid

Zn(CH3COO)2
Zink ethanoate

6CH3COOH + 2Al
Ethanoic acid

2Al(CH3COO)3 + 3H2
Aluminium ethanoate

10

+ H2

Reactions with bases

- Dilute ethanoic acid neutralizes alkalis such
as sodium hydroxide solution to give an
organic salt and water.
CH3COOH + NaOH CH3COONa + H2O
Ethanoic acid
Sodium ethanoate

- Black copper(II) oxide powder dissolves in

dilute ethanoic acid.
2CH3COOH + CuO Cu(CH3COO)2 + H2O
Ethanoic acid
Copper(II) ethanoate

11

Reactions with carbonates

- Dilute ethanoic acid reacts with metal
carbonates to produce a salt, carbon dioxide
and water.
2CH3COOH + Na2CO3 2CH3COONa + CO2 + H2O
Ethanoic acid
Sodium ethanoate

2CH3COOH + CaCO3 Ca(CH3COO)2 + CO2 + H2O

Ethanoic acid
Calcium ethanoate

12

Reactions with alcohols [Esterification]

Esterification:
Carboxilic acid reacts with alcohol to
produce an ester and water.
Concentrated
H2SO4
Carboxilic acid + Alcohol Ester +

Concentrated H2SO4 : catalyst

[will discuss more in next chapter]

13

Water

Uses of carboxilic acid:

i. Ethanoic acid is known as acetic acids use in;

- Food flavoring
- Food preservatives
- To make drugs, dyes, paints insectisides,
plastics
- To make esters for use as slovents
ii.
iii.
iv.
v.

Methanoic acid is used to coagulate latex.

Benzoic acids is used as food preservatives
Fatty acids used in making soaps
Carboxilic acids use in the manufactured of
polyester and polyamids (fibres) in textile
14

Conclusion on chemical reaction;

Carboxilic acid + reactive metal
carboxylate salt + hydrogen
Carboxilic acid + base
carboxylate salt + water
Carboxylate acid + metal carbonate
carboxylate salt + carbon dioxide +
Water
Carboxilic acid + alcohol
ester + water
1. Learning task 2.9 Summarizing pg 75
[notes book]
2. Effective Practise pg 75
1, 2, 3
[exercise book]
15

ESTER
General formula CnH2n+1COOCmH2m+1

R : alkyl group in carboxilic acid

R : alkyl group in alcohol
O

CnH2n + 1C OH + CmH2m+1OH
(carboxilic acid)

(alcohol)

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 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

CmH2m+1

Carboxilate
group, -COO-

17

Derived from
alcohol

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:
CH3COOH

+ CH3OH CH3COOCH3 + H2O

18

H
O
|

H C C OH
|
H

H
|
H C OH
|
H
CH3OH
(Methanol)

CH3COOH
(Etanoic acid)

H
O
H
|

|
H C C O C H + H2O
|
|
H
H
CH3COOCH3
(Methyl ethanoat)

Water

Example: ii. Ethanoic acid + ethanol

ethyl ethanoate + water
Chemical equation:
CH3COOH

+ CH3CH2OH CH3COOCH2CH3 + H2O

19

H
O
|

H C C OH
|
H

Ethanoic acid

H
H
|
|
H C C OH
|
|
H
H
Ethanol

H
O
H
H
|

|
|
H C C O C C H + H2O
|
|
|
H
H
H
ethyl etanoat
Water

Example: iii. Methanoic acid + Ethanol

ethyl methanoate + water
Chemical equation:
HCOOH

+ CH3CH2OH HCOOCH2CH3 + H2O

20

H C OH

Methanoic acid

H
H
|
|
H C C OH
|
|
H
H
Ethanol

O
H
H

|
|
H C O C C H + H2O
|
|
H
H
Ethyl metanoat

Air

Q: Draw structural molecule of

i. Methyl metanoate
ii. Pentyl propanoate
iii. Propyl ethanoate
Solutions; i. Methyl metanoate
21

Methyl methanoate
From carboxilic acid

From alcohol

Methanoic acid

Methanol

H C OH

H
|
H C OH
|
H
Break up and rejoin

O
H

|
H C O C H + H2O
|
H
methyl metanoate

ii. Pentyl propanoate

Try now

22

Air

23

Prophyl ethanoate
From carboxilic acid

From alcohol

Ethanoic acid
H O
|

H C C OH
|
H

Propanol
H
H H
|
|
|
H C C C OH
|
|
|
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
propyl ethanoate

24

Water

Preparation of ester through reflux

Tissel tube
Liebig
condenser

Water
out
Uniform
heating

Porcelain chip
To prevent
bumping and
ensure smooth
boiling

Water
in

Water
bath

XXXXXXXXXXXXXXX

To cold the
ethanol and
ethanoic acid

Ethanol +
ethanoic acid +
concentrated
sulphuric acid

How to carry out this process?

[Success pg 378]
After boiling, Liebig condenser is rearranged
To carry out the fractional distillation at
74oC 78oC to collect ethyl ethanoate.

25

Physical properties of ethyl ethanoate

- colourless
- fragrant smell
- insoluble in water
- lese dense in water
Natural Sources
- Most simple esters are found in fruits and
flowers.
ex: benzyl ethanoate in Jasmine
ethyl butanoate in pineapple

- Palm oil are liquid ester.

- The higher and complex ester does not
produce pleasant smells
26

Uses of ester

- to make perfume, cosmetics

- to make artificial food flavoring
[Text Book: Table 2.8 pg 81]
- used as organic solvents
eg. ethyl ethanoate used in sunburn
lotion, polish removers, glues.
- to make synthetic polymers/fabrics
- to make aspirin (pain reliever)
Exercise:
Effective Practise pg 84 no. 1-3
[Ex. Books]
Prepared by;
Kamal Ariffin Bin Saaim
SMKDBL
http://kemhawk.webs.com
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