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Which one of the following alkenes when treated with HCl yields majorly an anti Markovnikov product?

1. CH3O-CH=CH2
2. H2N-CH=CH2
3. F3C-CH=CH2
4. Cl-CH=CH2

Correct answer: F3C-CH=CH2

Solution

Ionic HCl addition follows the more stable carbocation. The strongly electron-withdrawing CF3 destabilizes a cation on the adjacent carbon, so the positive charge forms on the terminal CH2 instead, giving the anti-Markovnikov product. Hence F3C-CH=CH2.

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