Question

In all of the above described reactions, the electrophilic carbonyl and nucleophilic enolate have originated from the same carbonyl compound. These types of aldol reactions are called self-aldol condensations. It is also possible to carry out an aldol condensation between two different carbonyl compounds. These are known as Mixed or Crossed Aldol Condensations. 5. Shown below is an example of mixed aldol condensation reaction. Draw the complete arrow pushing mechanism for the formation of the product. (4 pts) Benzaldehyde + acetone + Benzaldehyde -> Aldol Condensation Product Step 1: Formation of enolate ion from acetone. Step 2: Nucleophilic attack of enolate ion on electrophilic carbonyl of benzaldehyde to form the first aldol intermediate. Step 3: Dehydration in presence of base to form the first aldol product.

          In all of the above described reactions, the electrophilic carbonyl and nucleophilic enolate have originated from the same carbonyl compound. These types of aldol reactions are called self-aldol condensations. It is also possible to carry out an aldol condensation between two different carbonyl compounds. These are known as Mixed or Crossed Aldol Condensations.

5. Shown below is an example of mixed aldol condensation reaction. Draw the complete arrow pushing mechanism for the formation of the product. (4 pts)

Benzaldehyde + acetone + Benzaldehyde -> Aldol Condensation Product

Step 1: Formation of enolate ion from acetone.

Step 2: Nucleophilic attack of enolate ion on electrophilic carbonyl of benzaldehyde to form the first aldol intermediate.

Step 3: Dehydration in presence of base to form the first aldol product.

In all of the above described reactions, the electrophilic carbonyl and nucleophilic enolate have originated from the same carbonyl compound. These types of aldol reactions are called self-aldol condensations. It is also possible to carry out an aldol condensation between two different carbonyl compounds. These are known as Mixed or Crossed Aldol Condensations.

5. Shown below is an example of mixed aldol condensation reaction. Draw the complete arrow pushing mechanism for the formation of the product. (4 pts)

Benzaldehyde + acetone + Benzaldehyde -> Aldol Condensation Product

Step 1: Formation of enolate ion from acetone.

Step 2: Nucleophilic attack of enolate ion on electrophilic carbonyl of benzaldehyde to form the first aldol intermediate.

Step 3: Dehydration in presence of base to form the first aldol product.

Added by Travis V.

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