What are the names of the aldol condensation products of acetone + 4-methylbenzaldehyde and acetone + 4-methoxybenzaldehyde?
4-methyl benzalacetone
To determine the names of the aldol condensation products of acetone with 4-methylbenzaldehyde and 4-methoxybenzaldehyde, we need to understand the process of aldol condensation.
Aldol condensation is a reaction between an aldehyde or ketone and an enol or enolate, resulting in the formation of a β-hydroxyaldehyde or β-hydroxyketone, respectively. This reaction involves the nucleophilic addition of the enol or enolate to the carbonyl carbon of the aldehyde or ketone, followed by dehydration to yield the aldol product.
First, let's identify the enol or enolate forms of acetone, 4-methylbenzaldehyde, and 4-methoxybenzaldehyde.
Acetone (propanone) can tautomerize into its enol form by the migration of a hydrogen atom from the α/β carbon to the oxygen. The enol form of acetone is called prop-1-en-2-ol.
4-methylbenzaldehyde can also undergo tautomerization to produce its enol form, which is 4-methylbenzene-1,3-diol.
4-methoxybenzaldehyde, on the other hand, can form the corresponding enolate form through deprotonation at the α-carbon adjacent to the carbonyl group. The enolate form of 4-methoxybenzaldehyde is known as 4-methoxybenzyl anion.
Now, we can proceed with the aldol condensation reactions.
1. Acetone + 4-methylbenzaldehyde:
The enol form of acetone (prop-1-en-2-ol) can react with 4-methylbenzaldehyde (4-methylbenzal) to form a β-hydroxy ketone. The aldol product can be named as 4-methyl-3-hydroxy-2-butanone.
2. Acetone + 4-methoxybenzaldehyde:
The enolate form of 4-methoxybenzaldehyde (4-methoxybenzyl anion) can undergo aldol condensation with acetone to produce a β-hydroxy ketone. The name of the aldol product would be 4-methoxy-3-hydroxy-2-butanone.
Therefore, the aldol condensation products of acetone + 4-methylbenzaldehyde and acetone + 4-methoxybenzaldehyde are 4-methyl-3-hydroxy-2-butanone and 4-methoxy-3-hydroxy-2-butanone, respectively.