Question

Pulegone on reaction with $KMnO_{4}$ forms:

• A. 3-methyl adipic acid and Acetone
• B. Acetylene, and 3-methyl adipic Acid
• C. Cyclohexanone and Acetic acid
• D. 3-methyl cyclohexanone, and Acetone

Hint:

Oxidative cleavage of pulegone is a classic method used to determine its structure by identifying the resulting smaller fragments.

Answer 1

The Correct Option is A

Step 1: Concept The reaction involves the oxidative cleavage of an unsaturated ketone using a strong oxidizing agent, potassium permanganate ($KMnO_{4}$).

Step 2: Meaning Pulegone is a monoterpene ketone with an exocyclic double bond. Oxidation typically breaks the double bond and can further oxidize the resulting fragments.

Step 3: Analysis Under vigorous oxidation with $KMnO_{4}$, the isopropylidene group of pulegone is cleaved to yield acetone. The remaining cyclic structure undergoes ring opening and oxidation to form a dicarboxylic acid.

Step 4: Conclusion The specific products of this degradation are 3-methyladipic acid and acetone. Final Answer: (A)