Identifying Directing Groups & Rxns with Benzene (Worksheet Solutions Walkthrough)

In this solution walkthrough, we go through the worksheet Identifying Directing Groups & Rxns with Benzene on jOeCHEM (worksheet and solution linked below).
Worksheet: worksheets.joechem.io/worksheets/Identifying%20Directing%20Groups%20and%20Reactions%20with%20Benzene.pdf
Solution: worksheets.joechem.io/worksheets/Answer-%20Directing%20Groups%20and%20Rxns%20with%20Benzene.pdf
Related instructional videos on jOeCHEM:
joechem.io/videos/28 - Directing Groups--Exploring Ortho/Para and Meta Directors
joechem.io/videos/192 - Directing Groups--Activating and Deactivating Benzene (via Resonance and Induction)
========================================
Follow jOeCHEM on social media:
If you're having an organic blast, please SUBSCRIBE: kzbin.info
LIKE and FOLLOW across social media:
Facebook - joechemio/
Instagram - joechem_io
TikTok - www.tiktok.com/@joechem

[@WomannequinReviews]

how does Cl donate electrons if it slightly deactivates the benzene ring by withdrawing electrons through its strong electronegativity?

[@jOeCHEM]

Hi Womannequin Reviews! So in my mind, the two most likely scenarios you encounter with directing groups are: EDG: the directing group, via resonance, pumps electrons INTO the benzene ring--activating the benzene ring for faster EAS reactions. When drawing the resonance out, the ortho/para gain negative charges, causing EAS reactions to add groups ortho/para. EWG: the directing group, via resonance, sucks electrons OUT of the benzene ring--deactivating the benzene ring for slower EAS reactions. When drawing the resonance out, the ortho/para gain postivie charges, causing EAS reactions to add groups meta to avoid the partially positive ortho/para locations. The halogens are weird, because they have a foot in each of the two buckets above: Halogens (EDG that directs groups ortho/para, but slightly deactivates the ring): Because the halogens are so electronegative and hate sharing their electrons, they inductively "withdraw" a bit of electron density from a benzene ring, making EAS reactions slower. HOWEVER, they still enable resonance structures to be drawn, and those resonance structures show the ortho/para gain negative charges, causing EAS reactions to add groups ortho/para. I know it's a weird thing to rectify in your mind, but does that make sense?