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in these reaction(Ts and Ms), why do they proceed in different mechanism/?

more specifically,

  1. (Ts) e- pair from O attacks S, (Ms)but not in latter reaction. why?

it makes no sense. because TsCl is more sterically hindered by benzene ring.

  1. in Ms, e- from hydroxyl group attack H attached to methyl group instead. I'm not famillar with H that was attached to C taken by other things. strong base can do this?

help me~

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marked as duplicate by bon, ron organic-chemistry Mar 12 '16 at 14:30

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    $\begingroup$ Don't post the same question twice. Edit your previous question if you want to add more information. $\endgroup$ – bon Mar 12 '16 at 13:42
  • $\begingroup$ okay. sorry T_T $\endgroup$ – NK Yu Mar 13 '16 at 6:51

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