Cyclohexanol to cyclohexanone is a common organic chemistry reaction that involves the oxidation of an alcohol to a ketone. This reaction can be performed using various oxidizing agents, but one of the most convenient and efficient methods is using chromic acid. In this article, we will explain how to oxidize cyclohexanol to cyclohexanone using chromic acid, and what are the advantages and disadvantages of this method.
What is Chromic Acid?
Chromic acid is a strong oxidizing agent that consists of a mixture of chromium trioxide (CrO3) and sulfuric acid (H2SO4). It has the formula H2CrO4, and it can be prepared by adding concentrated sulfuric acid to a solution of sodium or potassium dichromate. Chromic acid can oxidize primary alcohols to carboxylic acids, and secondary alcohols to ketones. It can also oxidize aldehydes, alkenes, and aromatic compounds.
How to Oxidize Cyclohexanol to Cyclohexanone Using Chromic Acid?
To oxidize cyclohexanol to cyclohexanone using chromic acid, you will need the following materials:
- Cyclohexanol
- Chromic acid solution
- Distilled water
- Ice bath
- Round-bottom flask
- Condenser
- Heating mantle
- Thermometer
- Separatory funnel
- Sodium bicarbonate solution
- Anhydrous sodium sulfate
- Rotary evaporator
The procedure is as follows:
- Add 10 mL of cyclohexanol and 20 mL of chromic acid solution to a 100 mL round-bottom flask. Attach a condenser and a thermometer to the flask, and place it on a heating mantle.
- Heat the mixture gently until it reaches 80 °C, and maintain this temperature for 30 minutes. The color of the solution will change from orange to green, indicating the oxidation of cyclohexanol to cyclohexanone.
- Cool the mixture in an ice bath, and transfer it to a separatory funnel. Add 50 mL of distilled water, and shake the funnel gently. Drain the lower aqueous layer, and keep the upper organic layer.
- Wash the organic layer with 25 mL of sodium bicarbonate solution, and drain the lower aqueous layer again. Repeat this step until no more gas bubbles are formed.
- Dry the organic layer with anhydrous sodium sulfate, and filter it into another round-bottom flask.
- Remove the solvent using a rotary evaporator, and collect the crude cyclohexanone.
- Purify the cyclohexanone by distillation or recrystallization, and measure its melting point and infrared spectrum.
Advantages and Disadvantages of Using Chromic Acid
Using chromic acid to oxidize cyclohexanol to cyclohexanone has some advantages and disadvantages, such as:
- Advantages:
- Chromic acid is a cheap and readily available oxidizing agent.
- Chromic acid can oxidize cyclohexanol to cyclohexanone in high yield and selectivity.
- Chromic acid can be easily prepared by mixing dichromate salts and sulfuric acid.
- Disadvantages:
- Chromic acid is highly corrosive and toxic, and requires special handling and disposal.
- Chromic acid can cause environmental pollution and health hazards if not properly treated.
- Chromic acid can overoxidize some substrates or react with other functional groups.
Conclusion
In conclusion, chromic acid is a useful oxidizing agent for converting cyclohexanol to cyclohexanone, but it also has some drawbacks that need to be considered. Therefore, it is important to choose the appropriate oxidizing agent for each specific reaction, depending on the desired product, yield, selectivity, cost, safety, and environmental impact.
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