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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

3
Butanoic
3
acid

Naming carboxilic acids

3 2 Carbon number 1

H H O

C C C
H H O H

Example 1:

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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

Example 2:

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Attached alkyl group: 2-methyl

Longest continuous chains: butanoic acid


H

CH3 C COOH
Carboxyl carbon: carbon number 1

C2H5

Name: 2-methylbutanoic acid

Example 3:
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H

C2H5 C COOH

Name: 2-ethyl pentanoic acid


C3H7

Example 4:
H

C3H7 C COOH

Name: 2-ethyl pentanoic acid

C2H5

Ethanoic Asid
Can be prepared through oxidation of an
ethanol.

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Chemical equation:

CH3CH2OH + 2[O] CH3COOH + H2O


Etanol ethanoic acid

K2Cr2O7 solutions
H H + H O
dilute H2SO4
H C C OH + 2[O] H C C OH + H2O
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
Label the
Water out
diagram please

Liebig condenser
Water
Retort
in
stand
Rounded bottom flask

Absolute ethanol, C2H5OH +


Wire Acidified potassium dichromate(VI),
xxxxxxxxxxxxxx
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?

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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

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
- 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

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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)

Esterification
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- 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
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- 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

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

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Example: ii. Ethanoic acid + ethanol
ethyl ethanoate + water
Chemical equation:

CH3COOH + CH3CH2OH CH3COOCH2CH3 + H2O

H O H H
| | |
H C C OH + H C C OH
| | |
H H H

Ethanoic acid Ethanol

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

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Example: iii. Methanoic acid + Ethanol
ethyl methanoate + water
Chemical equation:

HCOOH + CH3CH2OH HCOOCH2CH3 + H2O

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

Ethyl metanoat Air

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Q: Draw structural molecule of
i. Methyl metanoate
ii. Pentyl propanoate
iii. Propyl ethanoate

Solutions; i. Methyl metanoate

Methyl methanoate

From carboxilic acid From alcohol

Methanoic acid Methanol

O H
|
H C OH H C OH
|
H
Break up and rejoin

O H
|
H C O C H + H2O
|
H

methyl metanoate Air


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ii. Pentyl propanoate

Try now

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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 ethanoic acid
Water
in
Uniform Water
heating bath

Ethanol +
Porcelain chip ethanoic acid +
XXXXXXXXXXXXXXX
To prevent concentrated
bumping and sulphuric acid
ensure smooth
boiling

After boiling, Liebig condenser is rearranged


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

Physical properties of ethyl ethanoate


- colourless
- fragrant smell
- insoluble in water
- lese dense in water
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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

Uses of ester

- to make perfume, cosmetics


- to make artificial food flavoring
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- used as organic solvents
eg. ethyl ethanoate used in sunburn
lotion, polish removers, glues.
- to make synthetic polymers/fabrics
- to make aspirin (pain reliever)

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