Welcome Guest Search | Active Topics |

Tag as favorite
adding thionyl chloride to an alcohol
Options
Previous Topic Next Topic
Amna_5729
#1 Posted : Monday, July 20, 2020 6:32:15 PM
Rank: Newbie

Groups: Registered
Joined: 7/20/2020
Posts: 7

Thanks: 0 times
Was thanked: 0 time(s) in 0 post(s)
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?
Back to top
Report?
INSTR_Katerina_102
#2 Posted : Monday, July 20, 2020 6:35:16 PM
Rank: Advanced Member

Groups: Registered
Joined: 6/24/2019
Posts: 250

Thanks: 0 times
Was thanked: 0 time(s) in 0 post(s)
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
Back to top
Report?
Users browsing this topic
Guest
Tag as favorite
You cannot post new topics in this forum.
You cannot reply to topics in this forum.
You cannot delete your posts in this forum.
You cannot edit your posts in this forum.
You cannot create polls in this forum.
You cannot vote in polls in this forum.

Clean Slate theme by Jaben Cargman (Tiny Gecko)
Powered by YAF | YAF © 2003-2009, Yet Another Forum.NET
This page was generated in 0.077 seconds.