Replacing Alcohols with Chlorines with SOCl2 via Sn2

joechem.io/vid... for video on jOeCHEM and attached worksheet + solution (below video on jOeCHEM aka the link).
Study Guide: worksheets.joec...
In this video, we look at a nifty Sn2 reaction that enables us to replace alcohols with chlorides. For a VERY similar reaction (aka one that does this but with Br), check out joechem.io/vid...
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[@AutumnU]

Hey this was super useful! keep up the good work dude

[@jOeCHEM]

Thank you, Autumn! That means a lot :) And thank you for subscribing--I appreciate it a ton.

[@junkaccount2535]

Always coming through with the videos man! I can't tell you how much more I've used your vids over other org-chem channels, especially when I'm confused on a take-home exam. Most other tutors pretend that we all understand the details of molecular orbital theory 😂

[@jOeCHEM]

Haha, thank you for the kind words and for watching! I'm so pumped you found the video helpful.

[@momo82012]

Hi Joe, What makes you determine "good" leaving group and "bad" leaving group? Why OH considered as a bad leaving group and yet TsCl is a good ?

[@Gia1211]

Hey joe! Thanks for this wonderful video. I am not sure you might be able to see this comment, but for the very last reaction, does it ends with just a single oxygen, or is it end with OH but different configuration?

[@jOeCHEM]

Hi minkyung! Thanks for watching! I think I'm a bit confused: The purpose of the reaction at 6:46 is to say that instead of doing sn2 with a TWO step reaction (1st being to have the alcohol become a better leaving group by introducing TsCl and 2nd having Cl- from the NaCl perform sn2), you can just instead use SOCl2 in one step to attack the secondary carbon and perform sn2, yielding a wedged Cl. So in the product, there is NO oxygen (my handwriting is a bit messy, but that's a wedged Cl in the product). Did that clear anything up, or is there still confusion?