Grade 12

Grade 12Alcohol, 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:

  1. Formation of carbocation by protonation of alkene
  2. Attack of water on the carbocation
  3. 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.

A visual example

Ethanol: C2H5OH Dehydration: forms ethylene (C2H4) Oxidation: forms acetic acid ( CH3COOH ) Esterification: forms ethyl acetate (CH3COOCH2CH3)

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