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The 52 pages that link to Electrophilic aromatic substitution, each with the reason it gives.
AromaticityRelated: The reaction preserves the ring’s aromatic stabilization after a temporary loss of aromaticity.
BenzeneRelated: This reaction class preserves benzene’s aromatic ring during substitution.
Nucleophilic substitutionCompared with: The aromatic ring is attacked by an electrophile, reversing the roles seen in nucleophilic substitution.
PhenolRelated: Phenol’s hydroxyl group activates the ring and directs substitution mainly to ortho and para positions.
ElectrophileBroader topic: Aromatic rings capture electrophiles while ultimately preserving aromaticity.
Electrophilic additionCompared with: Aromatic rings restore aromaticity by substitution instead of retaining addition across the ring.
Polycyclic aromatic hydrocarbonRelated: It is a common route for adding substituents to PAH ring systems.
AnilineRelated: The amino group activates aniline’s ring and directs many substitutions to ortho and para positions.
PyridineCompared with: Pyridine’s electron deficiency makes this reaction harder than it is for benzene.
NaphthaleneRelated: Naphthalene commonly reacts by substitution rather than addition, preserving its aromatic system.
Nucleophilic aromatic substitutionCompared with: It reverses the polarity of the attacking species compared with nucleophilic aromatic substitution.
Aromatic compoundBroader topic: It is a central pathway for modifying aromatic rings without permanently disrupting aromaticity.
Friedel–Crafts reactionNarrower topic: Friedel–Crafts alkylation and acylation are members of this reaction family.
NitrationNarrower topic: This is the usual pathway for nitrating electron-rich aromatic rings.
PyrroleRelated: Pyrrole commonly reacts this way, often at a ring carbon adjacent to nitrogen.
AlkylationBroader topic: Friedel–Crafts alkylation is this reaction applied to aromatic rings.
IndoleRelated: Indole commonly reacts with electrophiles at its electron-rich C3 position.
Friedel–Crafts acylationNarrower topic: Acylation follows this general mechanism, including formation and loss of a sigma complex.
TolueneNarrower topic: The methyl group directs many ring substitutions toward the ortho and para positions.
Phenyl groupRelated: A phenyl ring can undergo this characteristic reaction when it has a replaceable ring hydrogen.
FuranRelated: Furan undergoes this reaction readily, chiefly at its 2-position.
NitrosationRelated: Some activated aromatic rings undergo carbon nitrosation by electrophilic substitution.
Azo compoundRelated: Azo coupling forms the new carbon–nitrogen bond through this reaction pattern.
BrominationRelated: Benzene bromination follows this pathway, with a Lewis acid activating bromine.
DiazotizationNarrower topic: Azo coupling, one major use of diazonium salts, proceeds by this reaction family.
SulfonationNarrower topic: Aromatic sulfonation proceeds by replacing a ring hydrogen with an electrophilic sulfur-containing group.
Aromatic hydrocarbonRelated: This reaction lets the ring form new bonds while recovering its aromatic electron system.
BenzimidazoleRelated: It provides a route to carbon-substituted benzimidazole derivatives.
Sulfonic acidRelated: Aromatic sulfonation commonly forms aryl sulfonic acids by this mechanism.
AnthraquinoneRelated: Substitution on the fused aromatic framework produces many functional anthraquinone derivatives.
ThiopheneNarrower topic: Thiophene commonly undergoes substitution rather than addition, retaining aromaticity.
ChlorobenzeneNarrower topic: Chlorobenzene undergoes this reaction family, though chlorine slows it relative to benzene.
AnisoleNarrower topic: Anisole’s characteristic ring reactions belong to this broader reaction family.
BenzonitrileRelated: The cyano group deactivates benzonitrile’s ring and directs substitution mainly to the meta position.
CarboraneCompared with: Carborane carbon vertices can undergo substitution, but their cage bonding is not ordinary aromatic-ring chemistry.
QuinolineRelated: Quinoline’s benzene portion undergoes this reaction more readily than its pyridine portion.
BiphenylRelated: Biphenyl’s rings undergo substitution reactions, with the second phenyl group influencing their reactivity.
CarbazoleRelated: Carbazole undergoes substitution on its electron-rich aromatic rings.
PyrazineCompared with: Pyrazine’s electron-poor ring is less reactive in this reaction than benzene.
Electrophilic substitutionBroader topic: This common form proceeds through a temporary loss and restoration of aromaticity.
IsoquinolineRelated: Isoquinoline’s electron-poor nitrogen influences where electrophilic substitution occurs.
IsoxazoleRelated: Isoxazole can undergo substitution, though its electron-poor ring affects reactivity and position.
NitrobenzeneNarrower topic: The nitro group deactivates the ring and directs incoming electrophiles mainly to the meta position.
PyrazoleRelated: Pyrazole’s ring can undergo electrophilic substitution, commonly at a carbon position.
ResorcinolRelated: Resorcinol’s hydroxyl groups activate its ring toward substitution reactions.
ThiazoleRelated: Thiazole undergoes electrophilic substitution most readily at the 5-position.
Arene substitution patternRelated: Existing substituents direct incoming groups toward characteristic positions on the ring.
AzuleneRelated: Azulene’s electron-rich framework undergoes electrophilic substitution, especially at the five-membered ring.
BenzofuranNarrower topic: It describes common substitution reactions of benzofuran’s electron-rich fused system.
Chlorosulfuric acidNarrower topic: Aromatic sulfonation with chlorosulfuric acid proceeds by electrophilic substitution.