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The expected product is 3-chloropropan-1,2-diol since secondary carbocation is more stable than primary but it is not formed.
I have surfed the internet a lot regarding this and none seems to be a simple, reasonable answer. Can anyone please explain this mechanism clearly.
The answer seems to be pretty simple, surprisingly.
I've asked my chemistry sir and this is what he said.
In the underlined step, 2° carbocation is supposed to be formed.
But there is -I effect from OH group which makes the carbocation close to it, that is, 2° carbocation less stable.
Hence to avoid that, 1° carbocation is formed away from OH group and then the nucleophile 'OH minus' from HOCl attacks the 1° carbocation so formed.
Thus, 2-chloropropan-1,3-diol is formed as an intermediate instead of 3-chloropropan-1,2 diol.
