Question
Question: Bring out the following conversions: Acetaldehyde to \(But-2-enal\)....
Bring out the following conversions:
Acetaldehyde to But−2−enal.
Solution
Aldol condensation is a condensation reaction of organic chemistry and in which enol or an enolate ion reacts with a carbonyl compound to form a β−hydroxyaldehyde. If the condensation reaction is present between two different carbonyl compounds it is called crossed Aldol condensation.
Complete step by step answer:
First we will discuss about the mechanism of Aldol condensation,
Mechanism: - In which hydroxide acts as a base and α−hydrogen act as an acid or produced enolate ion. This reaction can be seen as an acid base reaction.
The aldehydes attack at the electrophilic carbonyl carbon and as a result give alkoxide intermediate. The alkaloid deprotonates water molecules that produce hydroxide and β−hydroxyaldehyde.
Now we will discuss about the chemical reaction which is given in question,
Ethanal(acetaldehyde)→But−2−enal
2R−CHO+NaOH→R(OH)RCHO→RCHO+H2O
During the Aldol condensation, when acetaldehyde treated with the dilute alkali(NaOH), ethanal produced 3−hydroxybut−anal , then 3−hydroxybut−analis heated and the water molecules is liberated, as a result But−2−enal is formed.
2CH3CHO+NaOH→CH3−CH(OH)−CH2−CHO→H3C−CH=CH−CHO+(−H2O)
Ethanal+ dilute alkali→ 3−hydroxybut−anal→ But−2−enal+ water (liberated)
So according to this theoretical concept, the acetaldehyde is converted into But−2−enal in the presence of dilute alkali and by the liberation of water molecules due to the heating process.
Note: Aldol condensation is important in the organic chemistry for the synthesis of aldehydes and ketones. They provide a good way to form carbon-carbon bonds. The Robinson annulations reaction is a good example of an Aldol condensation.