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Disubstituted Benzenes: The Strongest Electron-Donor “Wins”

March 19, 2018 By James Ashenhurst 5 Comments

Having gone through the mechanism of electrophilic aromatic substitution, explored activating and deactivating substituents, and seen the importance of directing groups, let's now take the opportunity to use these concepts to answer some slightly thornier questions. For instance: What happens … [Read more...]

Filed Under: Aromatic Reactions, Organic Chemistry 2 Tagged With: activating, deactivating, directing groups, electrophilic aromatic substitution, meta, ortho, para

Why are halogens ortho- para- directors?

March 5, 2018 By James Ashenhurst 5 Comments

The previous post in this series tried to show that the key to understanding why a substituent is an ortho-, para- director or meta- director lies in understanding how it influences the stability of the ortho-, para- and meta- carbocation intermediates. In ortho- and para- addition, there's a … [Read more...]

Filed Under: Aromatic Reactions, Organic Chemistry 2 Tagged With: activating, deactivating, electrophilic aromatic substitution, halogens

Understanding Ortho, Para, and Meta Directors

February 2, 2018 By James Ashenhurst Leave a Comment

In the previous post we introduced ortho- ,para- and meta- directors in electrophilic aromatic substitution.  Previous to that we covered the mechanism of electrophilic aromatic substitution, and showed that the mechanism proceeds through a carbocation intermediate. Today, we're going to tie … [Read more...]

Filed Under: Aromatic Reactions, Organic Chemistry 2 Tagged With: activating, carbocation stability, deactivating, directing groups, electrophilic aromatic substitution, meta, nitration, ortho, para, reaction energy diagram

Ortho-, Para- and Meta- Directors in Electrophilic Aromatic Substitution

January 29, 2018 By James Ashenhurst 6 Comments

Two Important Reaction Patterns: Ortho- , Para- and Meta- Directors It's one thing to learn about electrophilic aromatic substitution reactions of benzene itself. But once you move beyond benzene, that's when things start getting really interesting. Here's a fascinating observation. Start … [Read more...]

Filed Under: Aromatic Reactions, Uncategorized Tagged With: activating, deactivating group, electrophilic aromatic substitution, ortho para meta

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