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When HBr is added to CH2=CH–OCH3 under dry conditions at room temperature, which product is formed?

1. BrCH2–CH2–OCH3
2. H3C–CHBr–OCH3
3. CH3CHO and CH3Br
4. BrCH2CHO and CH3OH

Correct answer: H3C–CHBr–OCH3

Solution

In methyl vinyl ether (CH2=CH-OCH3) protonation occurs at the terminal CH2 so the positive charge sits on the carbon bearing OCH3, where it is stabilised as an oxocarbenium ion. Br- then adds there to give CH3-CHBr-OCH3.

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