Pinacol Pinacolone Rearrangement Reaction Mechanism ; Step 1. Protonation of a hydroxyl group on the enol tautomer of pinacol results in the formation of an enol.
: Step 1. Protonation of a hydroxyl group on the enol tautomer of pinacol results in the formation of an enol. Step 2. The enol undergoes a keto-enol tautomerization to form the keto tautomer.
Step 3. The keto tautomer undergoes an aldol condensation with another molecule of ketone to form a β-hydroxy ketone.
Step 4. The β-hydroxy ketone is converted to an ester by reaction with an alcohol.
Step 5. Hydrolysis of the ester produces pinacolone.
What is Pinacol and Pinacolone?
Pinacol is a compound with the formula C6H4(CO)2. It is a colorless liquid with a camphor-like odor. Pinacol is produced by the reaction of an aldehyde with an alcohol in the presence of a base.
Pinacolone is a colorless liquid with a camphor-like odor. It is produced by the reaction of an aldehyde with an alcohol in the presence of a base.
Pinacol Pinacolone Rearrangement Reaction
The pinacol rearrangement reaction is a type of organic reaction that rearranges a carbon-carbon double bond in a molecule. The reaction is commonly used to produce pinacol from a molecule with a carbon-carbon double bond. The reaction is initiated by the removal of a hydrogen atom from one of the carbons in the double bond. This leaves a carbocation intermediate, which rearranges to form the product molecule.
Pinacol Pinacolone Rearrangement Reaction Mechanism
The rearrangement of pinacol to pinacolone is a two-step process. In the first step, the hydrogen on the carbon adjacent to the carbonyl is removed, and in the second step, the hydrogen on the carbon adjacent to the alcohol is removed.
Applications of Pinacolone (Product of Pinacol Rearrangement)
Pinacolone is a versatile molecule that can be used in a variety of applications. Some of the most common applications of pinacolone include:
1. As a precursor to pharmaceuticals.
2. In the production of plastics and other synthetic materials.
3. In the production of fuels and other chemicals.
4. In the production of dyes and other colorants.
5. In the production of fragrances and other aromatics.