JEE Main · 2020 · 07 Jan 2020 · Shift 1 · Alcohols Phenols and Ethers

1-methyl ethylene oxide when treated with an excess of HBr, produces

(A)(see structure)
(B)(see structure)
(C)(see structure)
(D)(see structure)
✓ Correct

Answer: (D)

Solution

Propylene oxide (1-methylethylene oxide) is protonated on oxygen by HBr, and bromide then opens the strained ring. With excess HBr the newly formed alcohol is also converted to a bromide, so both ring carbons end up bearing bromine, giving

C H_{3} CHBrC H_{2} Br

, 1,2-dibromopropane.

JEE Main · 2020 · 07 Jan 2020 · Shift 1 · Single correct option

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