JEE MainChemistryAlcohols Phenols and Ethers
Consider the substrate 3,3-dimethylbutan-2-ol. It is subjected to two separate reactions: Reaction 1: Treatment with concentrated H ₂ SO ₄ and heat to give major product A. Reaction 2: Treatment with CH ₃ COCl and pyridine to give major product B. Identify the IUPAC names of the major products A and B.
Options
- AA = 2,3-dimethylbut-2-ene ; B = 3,3-dimethylbutan-2-yl acetate
- BA = 3,3-dimethylbut-1-ene ; B = 3,3-dimethylbutan-2-yl acetate
- CA = 2,3-dimethylbut-2-ene ; B = 2,3-dimethylbutan-2-yl acetate
- DA = 2,3-dimethylbut-1-ene ; B = 3,3-dimethylbutan-2-yl acetate
Correct answer
A. A = 2,3-dimethylbut-2-ene ; B = 3,3-dimethylbutan-2-yl acetate
Step-by-step solution
Reaction 1: 3,3-dimethylbutan-2-ol reacts with conc. H ₂ SO ₄ upon heating. Protonation of the hydroxyl group followed by loss of water generates a secondary carbocation at C-2. A 1,2-methyl shift occurs to form a more stable tertiary carbocation at C-3. Subsequent loss of a proton yields the most substituted alkene, 2,3-dimethylbut-2-ene, as the major product A (Saytzeff's rule). Reaction 2: 3,3-dimethylbutan-2-ol reacts with CH ₃ COCl and pyridine. The oxygen atom of the alcohol acts as a nucleophile and attacks