Reaction involving markovnikov's rule Question:


Attempt:
The first reaction is addition of hydrogen halide. The reaction follows markovnikov's rule. The two possible products of the first reaction are:

For each product, the carbocations formed are:

After the formation of carbocation, $\ce{Cl-}$ attacks the carbocation forming a dihalide.
The final product after second reaction depends on the above intermediates.
The second carbocation faces electron withdrawing inductive effect and electron donating resonance effect from chlorine. But for halogens, inductive effect is more than resonance effect. So the carbocation is destabilized. So I chose option (A) as the answer since the first carbocation is formed.
But the answer given is (C) which means the second carbocation is formed.
Indeed the second carbocation is formed.  It's favored by the chlorine atom being able to delocalize the charge through resonance, draw resonance hybrids for the second cation and you should see it.  In a sense you might say that the carbon bonded to chlorine is more effectively substituted for stabilizing the cation and so the Markovnikov rule is "bent" accordingly.

The usual version of the Markovnikov rule is for hydrocarbon substrates.