Question

Show how cyclohexanecarboxylic acid could be synthesized from cyclohexane in good yield.

Short answer

Question: Explain how to synthesize cyclohexanecarboxylic acid from cyclohexane with good yield in a step-by-step process. Answer: To synthesize cyclohexanecarboxylic acid from cyclohexane with good yield, follow these steps: 1. Partially oxidize cyclohexane to cyclohexanol using potassium permanganate (KMnO4) in tert-butyl alcohol at room temperature. 2. Oxidize cyclohexanol to cyclohexanone using an oxidizing agent like pyridinium chlorochromate (PCC) or sodium dichromate (Na2Cr2O7) under anhydrous conditions at room temperature. 3. Convert cyclohexanone to cyclohexanecarboxylic acid through oxidative carboxylation using KMnO4 or potassium dichromate (K2Cr2O7) in dimethyl sulfoxide (DMSO) at room temperature, followed by acidic workup.

Step-by-step solution

Oxidation of Cyclohexane to Cyclohexanol

The first step in the synthesis is to convert cyclohexane into cyclohexanol. This can be done through the partial oxidation of cyclohexane using a suitable oxidizing agent. One common method is to use a mixture of potassium permanganate (KMnO4) and an organic solvent (e.g., tert-butyl alcohol). The reaction conditions should be around room temperature and the reaction should be carried out in the absence of water to prevent over-oxidation. Cyclohexane + KMnO4 (in tert-butyl alcohol) → Cyclohexanol

Oxidation of Cyclohexanol to Cyclohexanone

The next step is to further oxidize cyclohexanol to cyclohexanone. This can be done by using a suitable oxidizing agent like pyridinium chlorochromate (PCC) or sodium dichromate (Na2Cr2O7). The reaction should be carried out at room temperature under anhydrous conditions for a good yield of cyclohexanone. Cyclohexanol + PCC (or Na2Cr2O7) → Cyclohexanone

Oxidative Carboxylation of Cyclohexanone to Cyclohexanecarboxylic Acid

The final step in the synthesis is the conversion of cyclohexanone into cyclohexanecarboxylic acid through oxidative carboxylation. This can be achieved by using a suitable reagent, such as potassium permanganate (KMnO4) or potassium dichromate (K2Cr2O7), followed by acidic workup. The reaction should be carried out in an aprotic polar solvent like dimethyl sulfoxide (DMSO) at room temperature. Cyclohexanone + KMnO4 (or K2Cr2O7) in DMSO → Cyclohexanecarboxylic Acid (after acidic workup) Thus, through these three steps - partial oxidation of cyclohexane to cyclohexanol, oxidation of cyclohexanol to cyclohexanone, and oxidative carboxylation of cyclohexanone - we can synthesize cyclohexanecarboxylic acid from cyclohexane in good yield.