Grade 12 → Alcohol, phenol and ether ↓
Preparation and properties of alcohols
Introduction
Alcohols are organic compounds containing one or more hydroxyl (-OH
) groups attached to a carbon atom. The general formula of alcohols is CnH2n+1OH
. They are versatile in nature and have various applications in industries and daily life.
Preparation of alcohol
There are several methods for preparing alcohol, including fermentation, hydration of alkenes, and reduction of carbonyl compounds.
1. Fermentation
Fermentation is one of the oldest methods for producing alcohol, particularly ethanol. It involves converting sugars into alcohol and carbon dioxide by the action of yeast or bacteria.
C6H12O6 (glucose) --yeast--> 2 C2H5OH (ethanol) + 2 CO2
2. Hydration of alkenes
Alcohols can be formed by hydrating alkenes. This process involves the addition of water to the double bond in the presence of an acid catalyst.
Mechanism:
- Formation of carbocation by protonation of alkene
- Attack of water on the carbocation
- Deprotonation to form alcohols
CH2=CH2 --H2O/H+ --> CH3CH2OH
Example: Ethene can be converted into ethanol using this method.
3. Reduction of carbonyl compounds
Aldehydes and ketones can be reduced to alcohols using reducing agents such as lithium aluminium hydride (LiAlH4
) or sodium borohydride (NaBH4
).
RCHO + 2 [H] --LiAlH4 --> RCH2OH (primary alcohol)
RCOR' + 2 [H] --NaBH4 --> RCH(OH)R' (secondary alcohol)
Example 1: Acetaldehyde when reduced gives ethanol.
Example 2: Acetone when reduced forms isopropanol.
Properties of alcohol
Alcohols exhibit unique physical and chemical properties due to the presence of the hydroxyl group.
1. Physical properties
- Boiling point: Alcohols have a higher boiling point than hydrocarbons of the same molecular weight. This is due to hydrogen bonding between alcohol molecules.
- Solubility: The following alcohols are soluble in water due to hydrogen bonding. Solubility decreases as the length of the carbon chain increases.
- Odour: Many alcohols have a distinctive odour, for example, methanol has a slight alcohol-like odour, while ethanol has a spirit-like odour.
Comparison: Methanol (CH3OH
) is more soluble in water than octanol (CH3(CH2)7OH
).
2. Chemical properties
Alcohols can undergo a variety of chemical reactions, which are useful for the synthesis of other compounds.
a) Dehydration
When heated with a strong acid such as sulfuric acid, alcohols can lose a water molecule to form an alkene.
CH3CH2OH --H2SO4/heat--> CH2=CH2 + H2O
Example: Ethylene can be formed by dehydrating ethanol.
b) Oxidation
Depending on the type of alcohol and the conditions, alcohols can be oxidized to form aldehydes, ketones, or carboxylic acids.
RCH2OH (primary alcohol) --[O]--> RCHO (aldehyde) --[O]--> RCOOH (carboxylic acid)
R2CHOH (secondary alcohol) --[O]--> R2CO (ketone)
Example 1: Ethanol can be oxidized to acetaldehyde and further to acetic acid.
Example 2: Isopropanol can be oxidized to acetone.
c) Esterification
Alcohols react with carboxylic acids in the presence of an acidic catalyst to form esters and water.
RCOOH + R'OH --H2SO4 --> RCOOR' + H2O
Example: Ethanol and acetic acid react to form ethyl acetate.
Conclusion
Alcohols are essential compounds in organic chemistry, with varied preparation methods and a wide range of physical and chemical properties. Understanding these properties allows chemists to use alcohols in a variety of industrial and laboratory applications.