Reaction MechanismhardMCQ SINGLE

When neopentyl alcohol () is forcefully heated with concentrated sulfuric acid (), what is the dominReaction 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?

Answer: C

💡 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.

💬
Still have doubts about this question?
Send it to our AI chemistry tutor on WhatsApp — gets answered in minutes
Ask on WhatsApp →

Practice 22,000+ questions like this

AI-adaptive practice, video lectures, and full JEE Advanced Chemistry content — all in one place.

JEE Advanced · JEE Mains · NEET · IChO · AP Chemistry