Grade 12 → Aldehydes, ketones and carboxylic acids ↓
Preparation and properties of aldehydes and ketones
Aldehydes and ketones are organic compounds that contain a carbonyl functional group, which is a carbon atom double bonded to an oxygen atom (C=O
). This group plays an important role in the chemistry of aldehydes and ketones, affecting their reactivity and properties. Understanding the preparation and properties of these compounds is essential in organic chemistry.
Oxidation of primary alcohols
Aldehydes can be formed by oxidizing primary alcohols. This is usually done using oxidizing agents such as pyridinium chlorochromate (PCC) or Dess-Martin pyridine, which allow selective oxidation of alcohols.
RCH2OH + [O] → RCHO + H2O
For example, ethanol can be oxidized to ethanol:
CH3CH2OH + [O] → CH3CHO + H2O
Hydroformylation of alkenes
Alkenes can be converted into aldehydes by reacting with carbon monoxide and hydrogen in the presence of a catalyst. This process is known as hydroformylation.
RCH=CH2 + CO + H2 → RCH2CH2CHO
Hydroformylation is used on a large scale in industry to produce aldehydes.
Oxidation of secondary alcohols
Ketones can be formed by oxidizing secondary alcohols. Common oxidizing agents include acidic potassium dichromate.
R2CHOH + [O] → R2CO + H2O
For example, cyclohexanol can be oxidized to cyclohexanone:
C6H11OH + [O] → C6H10O + H2O
Friedel–Crafts acylation
In the Friedel-Crafts acylation an acyl group is inserted into an aromatic ring to form a ketone. This is usually achieved using acid chlorides in the presence of a Lewis acid catalyst such as aluminum chloride (AlCl3
).
C6H6 + RCOCl → C6H5COR
Benzene reacts with acetyl chloride to form acetophenone:
C6H6 + CH3COCl → C6H5COCH3 + HCl
Physical properties
The presence of the carbonyl group gives aldehydes and ketones unique physical properties. They have higher boiling points than hydrocarbons of similar molecular weight due to the polarity of the carbonyl group, which allows dipole-dipole interactions. However, they have lower boiling points than alcohols because they cannot form hydrogen bonds with each other.
Chemical properties
Nucleophilic addition reactions
The carbon in the carbonyl group is electrophilic and susceptible to attack by nucleophiles. This is the basis for nucleophilic addition reactions, which are common reactions for aldehydes and ketones.
Cyanohydrin formation
When aldehydes or ketones react with hydrogen cyanide (HCN
), they form cyanohydrins.
RCHO + HCN → RCH(OH)CN
Reduction to alcohol
Aldehydes and ketones can be reduced to their corresponding alcohols using reducing agents such as lithium aluminium hydride (LiAlH4
) or sodium borohydride (NaBH4
).
RCHO + H2 → RCH2OH R2CO + H2 → R2CH(OH)
Oxidation reactions
Aldehydes are easily oxidized to carboxylic acids in the presence of oxidizing agents such as potassium permanganate (KMnO4
) or chromic acid. However, ketones are generally resistant to oxidation without breaking the C-C bond.
Aldehydes and ketones are valuable in a variety of fields, including industry and biology. Aldehydes such as formaldehyde are used in the manufacture of plastics and resins. Acetone, a well-known ketone, is used as a solvent in cleaning and in the textile industry. These compounds are also present in a variety of biochemical pathways and are important intermediates in organic synthesis.
The preparation and properties of aldehydes and ketones are fundamental concepts in chemistry. The methods for preparing these compounds - oxidation of alcohols, hydroformylation of alkenes, and Friedel-Crafts acylation - along with their physical and chemical properties make them versatile and widely used in chemical processes and industrial applications.