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What is the product when phenol reacts with conc. $\ce{H2SO4}$ in excess?

I have been told that the major product will be ortho at low temperature and para at high temperature. Why cannot it form both ortho- and para-substituted product as in the case of picric acid?

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It's a reversible reaction, so at higher temperature the thermodynamic para product is formed from the kinetic ortho product.

Further reading here 1

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  • $\begingroup$ Why does it only form a monosulphonated product and why not a trisulphonated product $\endgroup$ – Jash Nov 26 '19 at 11:54
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    $\begingroup$ Because the mono-product is strongly electron-withdrawn and the electrophile is not as good as NO2+ $\endgroup$ – Waylander Nov 26 '19 at 12:07
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    $\begingroup$ And because the forcing conditions needed to further sulfonate cause a range of other oxidative reactions leading to a complex mixture. $\endgroup$ – Waylander Nov 27 '19 at 14:20

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