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CC Lesson 3A
Divya_4978
#1 Posted : Wednesday, June 17, 2020 3:30:34 AM
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Hello,
On page 177 in the chem course companion I am a bit confused of the reaction regarding the addition of thionyl chloride to an alcohol.

When the OH group attacks the thionyl chloride, why does the oxygen have a positive charge when it attaches to the Sulfur? I thought the oxygen was a nucleophile attacking the sulfur (electrophile) and hence bears a negative charge.

Thank you in advance.
INSTR_Katerina_102
#2 Posted : Wednesday, June 17, 2020 10:05:30 PM
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https://imgur.com/a/BRi43tR

Neutral nucleophiles pretty much always gain a positive formal charge upon attacking something because they are attacking with a lone pair that formally belongs to them, and that lone pair forms a bond with an electrophile.

This results in a bond where the electrons that previously both belonged to the nucleophile now are shared between the two atoms.

This formal positive charge is often immediately dissipated by the deprotonation of the species.

A nucleophile is electron rich, which can mean it has a formal negative or an excess of electrons BEFORE attacking. After it has acted as a nucleophile, the product tends not to be considered a nucleophile anymore (at least without further deprotonation).

It has already "nuclophiled" and settled down.
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