Chapter 23 Alcohols and Carboxylic Acids

O Level Chemistry
Chapter 23 Alcohols and Organic Acids

Alcohols
A homologous series containing the OH functional group: hydroxyl group
They have the general formula, CnH2n+1OH.
-OH group is covalent. It is
Each member differs from the member before it by CH2. different from OH- ions in bases.
Names of alcohol ends with -ol.
Alcohols are soluble in water, colourless liquids and have low boiling points.
As the number of carbon atoms , boiling point , but solubility in water.
Ethanol is the most common alcohol.

No. of C Molecular Condensed structural

Name Structural formula
atoms formula formula

2 Ethanol C2H5OH CH3CH2OH

3 Propanol C3H7OH CH3CH2CH2OH

Preparation of Ethanol
1) By fermentation of sugars with yeasts
- Fermentation is a chemical reaction where sugars are broken down into smaller molecules by micro-
organisms (e.g. yeasts).

yeast
Glucose Ethanol + Carbon dioxide
C6H12O6 (aq) 2C2H5OH (aq) + 2CO2 (g)

- Sugars can be used for the fermentation process to make alcoholic drinks.
- Reaction takes place in the absence of oxygen.
- Speed of reaction is fastest at 37 C.
- Only a dilute solution of about a maximum 18% of ethanol is formed. (Why?)
- Fractional distillation can separate ethanol from the solution to increase its concentration.
2) From Ethene

- Ethene and steam are passed over a hot catalyst of phosphoric acid at 300 C and 65 atmospheres.
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 Chapter 23 Alcohols and Carboxylic Acids

- A mixture of ethanol and water is formed. Ethanol can be separated from water by fractional
distillation.
Reactions of Alcohol
Most chemical properties of alcohols are determined by the hydroxyl group (-OH).
1) Combustion
Alcohol + Oxygen Carbon dioxide + Water
C2H5OH (aq) + 3O2 (g) 2CO2 (g) + 3H2O (l)

2) Oxidation
Acidified potassium dichromate(VI)
Alcohol + [O] Organic acid + Water solution is a mixture of sulfuric acid and
potassium dichromate(VI) solution
C2H5OH (aq) + 2[O] CH3COOH (aq) + H2O (l)
- Ethanol is warmed with acidified potassium dichromate (VI) solution to give ethanoic acid.
- Ethanol is oxidised to ethanoic acid.
- Dichromate(VI) ions, Cr2O72- (orange), are reduced to chromium(III) ions, Cr3+ (green).
- Ethanol can also be oxidised to ethanoic acid by air.

3) Reaction with Organic Acids

Alcohol + Organic acid Ester + Water

Uses of ethanol
Solvent for paints, varnishes, perfumes, deodorants
Alcoholic drinks
Fuel for vehicles e.g. race cars
To make ethanoic acid for preserving food and making esters

Organic Acids (Carboxylic Acids)

A homologous series containing the -COOH functional group: carboxyl group.
They have the general formula CnH2n+1COOH.
Each member differs from the next member by CH2.
Their chemical names end with oic acid.
The first four carboxylic acids are liquid at room conditions: methanoic acid to butanoic acid
As the number of carbon atoms increase, boiling points also increase.
Ethanoic acid is an important member of the family.

No. of C Molecular Condensed structural

Name Structural formula
atoms formula formula
Methanoic
1 HCOOH HCOOH
acid

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 Chapter 23 Alcohols and Carboxylic Acids

Butanoic
4 C3H7COOH CH3CH2CH2COOH
acid

Preparation of Ethanoic Acid

1) By oxidation of ethanol with acidified K2Cr2O7. (above)
2) By oxidation of ethanol by atmospheric oxygen
- Done by enzymes in bacteria.

bacteria
C2H5OH (aq) + 2O2 (g) CH3COOH (aq) + H2O (l)

- Vinegar (solution of ethanoic acid in water) is made this way

- When beer or wine is exposed to air for a few days, they turn sour due to the formation of vinegar.
3) From natural gas using air and special catalysts.

2CH4 (g) + 2O2 (g) catalysts CH3COOH (aq) + 2H2O (l)

Reactions of Carboxylic Acids

Carboxylic acids are weak acids.
But they still react like a typical acid.
1) With reactive metals
2CH3COOH (aq) + Mg (s) Mg(CH3COO)2 (aq) + H2 (g)
Ethanoic acid magnesium ethanoate

2) With bases
CH3COOH (aq) + NaOH (aq) CH3COONa (aq) + H2O (l)
3) With metal carbonates
2CH3COOH (aq) + Na2CO3 (aq) 2CH3COONa (aq) + CO2 (g) + H2O (l)
4) Carboxylic acids reacting with Alcohols
- They form esters in the presence of a little concentrated sulfuric acid.

Carboxylic acid + Alcohol Ester + Water

CH3COOH (aq) + C4H9OH (aq) CH3COOC4H9 (aq) + H2O (l)

- This reaction is called esterification.

- Esters are insoluble in water but are good solvents for other compounds.
- Thus, they form a colourless layer on top of the water after the reaction.

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 Chapter 23 Alcohols and Carboxylic Acids

Esters
An organic compound formed from the reaction between an alcohol and a carboxylic acid.
This reaction is called esterification.
Esters are neutral, sweet-smelling, colourless liquids with low boiling points.
They can be found naturally in fruits. Uses of Esters
They are good solvents for organic compounds. Flavourings for food stuff
Perfumes
Solvents (in nail polish remover,
for glues and paints, etc.)
Ester:

Naming Esters
CH3COOH (aq) + C4H9OH (aq) CH3COOC4H9 (aq) + H2O (l)
ethanoic acid butanol butyl ethanoate
- The 1st part is the hydrocarbon part of alcohol with a -yl.
- The 2nd part is the part of acid with the suffix -oate.
- Hence the ester formed above is called butyl ethanoate as it comes from butanol and ethanoic acid.

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 Chapter 23 Alcohols and Carboxylic Acids

Chapter 22 & 23 Summary

Alkanes Cl2
Chloroalkane
CC in light
O2
Hydrogenation Cracking
(H2 and
Nickel catalyst) Bromoalkane
Br2
*A test for unsaturated compounds
O2
CO2 and H2O Alkenes
via combustion C=C
Many alkene
molecules Polymers
Steam,
H3PO4 catalyst H H
O2 300 C, 65 atm.
CC

Alcohols H H
OH n
Fermentation
With yeasts K2Cr2O7
*A test for Esterification
alcohols In dil. H2SO4, Esters
Alcohol and
Warmed
Glucose Carboxylic acid, CO
with conc. H2SO4
Carboxylic Acids O
COOH

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 Chapter 23 Alcohols and Carboxylic Acids

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