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adding thionyl chloride to an alcohol
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Amna_5729
#1 Posted : Monday, July 20, 2020 6:32:15 PM
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pg 177 of CC: the oxygen in ethanol attacks the sulfur in thionyl chloride but wouldn't sulfur be a better nucleophile than oxygen (since nucleophilicity increases going down a group)? Also, why is the sulfur electrophilic if it has a lone pair already?
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INSTR_Katerina_102
#2 Posted : Monday, July 20, 2020 6:35:16 PM
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Hi,

The sulfur in thionyl chloride is rendered more electrophilic because it is bonded to the highly electronegative Cl and O atoms.

As a result, despite possessing a lone pair, it is pretty electronegative. It also contains good leaving groups in Cl-.

Atom identity is important, but you'd have to compare apples to apples - for example a thiol (RSH) is more nucleophilic than an alcohol (ROH).

Hope this helps!

Katt
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