Selectivity in tosylation of sulphur and oxygen

### Problem



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> [![enter image description here](https://i.stack.imgur.com/q3Zoe.png)](https://i.stack.imgur.com/q3Zoe.png)
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### Answer



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>  **C**
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> 


### Question


The first step involves a nucleophilic substitution on the sulphur atom of the tosyl group. I reasoned that in the cyclohexane substrate, the sulphur atom (thiol group) will be more nucleophilic than the oxygen atom (alcohol group) due its larger size, higher polarizability and less solvation. Accordingly I proceeded by the following mechanism -


[![enter image description here](https://i.stack.imgur.com/XFW5Z.png)](https://i.stack.imgur.com/XFW5Z.png)


which gives **D** as the answer. Where am I going wrong?


