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Is this allylic chloride formed by an ionic or radical mechanism? Is it the more stable isomer?

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    $\begingroup$ Don't base product distributions on thermodynamics unless there is an equilibrium that can be established. You should be looking at kinetic considerations instead. $\endgroup$ – Zhe May 4 '18 at 13:23
  • $\begingroup$ I wonder if this actually is a free radical reaction. Afaik, the peroxide effect operates only in the case of HBr... $\endgroup$ – Gaurang Tandon May 4 '18 at 13:30
  • $\begingroup$ Yes you are right. $\endgroup$ – Amit Aniket May 4 '18 at 13:32
  • $\begingroup$ But the question still remains unsolved. $\endgroup$ – Amit Aniket May 4 '18 at 13:32
  • $\begingroup$ Which is the best site for the carbocation? $\endgroup$ – Waylander May 4 '18 at 15:18

Benzylic carbocation is formed as it is stable due to resonance. So Cl attaches to benzylic position. More substituted alkenes are more stable so the terminal double bond changes its position. (Also this isn’t free radical reaction)

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