When neopentyl alcohol () is forcefully heated with concentrated sulfuric acid (), what is the domin — Reaction Mechanism Chemistry Question
Question
When neopentyl alcohol ($2,2-dimethylpropan-1-ol$) is forcefully heated with concentrated sulfuric acid ($H_2SO_4$), what is the dominant elimination product?
💡 Solution & Explanation
Although neopentyl alcohol lacks $\beta$ -hydrogens, ruling out direct $E2$, it undergoes acid-catalyzed $E1$ dehydration. Initial protonation and loss of water yields a highly unstable primary neopentyl carbocation. This intermediate instantly undergoes a 1,2-methyl shift to generate the stable tertiary $tert$ -amyl carbocation. Subsequent loss of an adjacent proton yields the thermodynamically favored Saytzeff product, 2-methyl-2-butene.