CARBOXILIC ACID

General formula CnH2n+1COOH

One hydrogen atom is replaced with functional

group – COOH

Formula: HCOOH Formula: CH3COOH

O H O
║ | ║
H — C — OH H — C — C — OH
|
H
CARBOXYL GROUP

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Why families known as carboxylic ‘acid’

Carboxyl group plays a vital role to gives

acidic properties to carboxilic acid families.

CH3COOH H+ + CH3COO-

Ethanoic Hydrogen Ethanoate

acid ion ion

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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 C H Attached alkyl group: 2-methyl

H
Name: 2-methylpropanoic acid

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Example 2:
Attached alkyl group: 2-methyl

Longest continuous chains: butanoic acid

H
CH3 C COOH
Carboxyl carbon: carbon number 1

C2H5

Name: 2-methylbutanoic acid

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Example 3:
H
C2H5 C COOH

Name: 2-ethyl pentanoic acid

C3H7

Example 4:
H
C3H7 C COOH

Name: 2-ethyl pentanoic acid

C2H5

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Ethanoic Asid
Can be prepared through oxidation of an
ethanol.
Chemical equation:

CH3CH2OH + 2[O] → CH3COOH + H2O

Etanol ethanoic acid

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

This is carried out by refluxing ethanol with

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

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Preparation of ethanoic acid through refluxing
Tissel tube

Water out Label the

diagram please

Liebig condenser
Retort Water
stand in
Rounded bottom flask

Absolute ethanol, C2H5OH +

Wire xxxxxxxxxxxxxx Acidified potassium dichromate(VI),
gauge 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? (must proc]

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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

Ethanoic acid is a weak acid. Why?

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

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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

6CH3COOH + 2Al → 2Al(CH3COO)3 + 3H2

Ethanoic acid Aluminium ethanoate

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Reactions with bases (5.2)
- 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

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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

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Reactions with alcohols [Esterification]

Esterification:

Carboxilic acid reacts with alcohol to

produce an ester and water.

Concentrated
H2SO4
Carboxilic acid + Alcohol ———→ Ester + Water

Concentrated H2SO4 : catalyst

[will discuss more in next chapter]

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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. Methanoic acid is used to coagulate latex.

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

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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]

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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)

O
║
CnH2n + 1C — O — CmH2m+1 + H2O
(ESTER)

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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-

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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

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 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

Example: ii. Ethanoic acid + ethanol

 ethyl ethanoate + water
Chemical equation:

CH3COOH + CH3CH2OH → CH3COOCH2CH3 + H2O

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 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

Example: iii. Methanoic acid + Ethanol

 ethyl methanoate + water
Chemical equation:

HCOOH + CH3CH2OH → HCOOCH2CH3 + H2O

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 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

Ethyl methanoate Water

Q: Draw structural molecule of

i. Methyl metanoate
ii. Pentyl propanoate
iii. Propyl ethanoate

Solutions; i. Methyl metanoate

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 Methyl methanoate

From carboxilic acid From alcohol

Methanoic acid Methanol

H
O |
║ H— C — OH
H — C — OH |
H

Break up and rejoin

O H
║ |
H — C — O — C — H + H2O
|
H

methyl methanoate Water

ii. Pentyl propanoate

Try now

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23
 Prophyl ethanoate

From carboxilic acid From alcohol

Ethanoic acid Propanol

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

propyl ethanoate Water

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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

How to carry out this process?

[Success pg 378] [pg 49 prac book]

After boiling, Liebig condenser is rearranged

To carry out the fractional distillation at
74oC – 78oC to collect ethyl ethanoate.

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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

- Palm oil are liquid ester.

- The higher and complex ester does not
produce pleasant smells
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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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