Organic chemistry

Aldol condensation of Cyclohexanone (Step by step)

We already know about What is Aldol Condensation ?

So now we are going to solve same the aldol condensation of cyclohexanone. The chemical formula for the cyclohexanone is C6H10O. The structure of the cyclohexanone is given below

cyclohexanone

General Reaction (aldol condensation of cyclohexanone)

Generally the aldol condensation of cyclohexanone occurs as a Inter-molecular aldol condensation

aldol condensation of cyclohexanone

  • Carbanion is formed as intermediate
  • It is an Nucleophilic addition reaction
  • Hydroxide functions as a base
  • It also undergoes dehydration and gives condensation product

Reaction Mechanism :

The reaction mechanism for aldol condensation of cyclohexanone is a step wise process.

Step 1 : (Formation of Carbanion)

In the first step of the cyclohexanone aldol reaction, an carbanion gets formed as usual like a normal aldol condensation. The Base (Hydroxide ion) abstract the Alpha-Hydrogen of the cyclohexanone. This molecule contains two Alpha-Carbons (Carbon that present nearby to functional group attached carbon) so here any of the Alpha-Hydrogen can abstracted. It leads to formation of carbanion. And it undergoes Enolate-carbanion stabilization

aldol condensation of cyclohexanone

Step 2 : (Attack on Electrophilic Centre)

In this step, the formed carbanion in previous step is attack the Electrophilic Centre of another cyclohexanone molecule. That’s why it is called as Inter-molecular aldol condensation

aldol condensation of cyclohexanone (attack)

Step 3 : (Acid workup)

Here just a bit of acid is added to convert the enolate oxygen ion into its hydroxy form and the formed product is called as Aldol product of cyclohexanone

Aldol product of cyclohexanone

Step 4 : (Dehydration)

The formed aldol product of cyclohexanone undergoes dehydration with higher temperature and it forms the condensation product (Water molecule is eliminated)

aldol condensation product of cyclohexanone

Conclusion :

  • Aldol condensation of cyclohexanone is a Nucleophilic Addition Reaction
  • Hydroxide ions are used as Base
  • It involves Carbanion Intermediates
  • It is an Inter-molecular Aldol condensation
  • The product formed in this reaction is [1,1′-bi(cyclohexylidene)]-2-one

What is the product of aldol condensation of cyclohexanone ?

The product of the Aldol condensation of cyclohexanone is [1,1′-bi(cyclohexylidene)]-2-one

 

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