JEE MainChemistryAlcohols Phenols and Ethers
When 1-methylcyclopentanol is heated with concentrated H ₂ SO ₄ , it undergoes dehydration to give a major product P. The compound P is then treated with a cold, dilute aqueous solution of KMnO ₄ to yield the major product Q. The product Q is:
Options
- Atrans-1-Methylcyclopentane-1,2-diol
- Bcis-3-Methylcyclopentane-1,2-diol
- Ccis-1-Methylcyclopentane-1,2-diol
- D5-Oxohexanoic acid
Correct answer
C. cis-1-Methylcyclopentane-1,2-diol
Step-by-step solution
Dehydration of 1-methylcyclopentanol with concentrated H ₂ SO ₄ follows Saytzeff's rule, yielding the more substituted alkene as the major product. Thus, the major product P is 1-methylcyclopentene. Treatment of 1-methylcyclopentene with cold, dilute aqueous KMnO ₄ (Baeyer's reagent) brings about the syn-addition of two hydroxyl groups across the double bond. Because the addition is syn, the two -OH groups attach to the same face of the cyclopentane ring. This stereospecific reaction produces cis-1-methylcyclopenta