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Module 9 in the Syllabus

Reactions of Aromatic Compounds
Video seminar on the Reactions of Aromatic Compounds from the WikiPremed MCAT Course

Aromatic Compounds Mechanisms
Mechanisms and explanations from the Organic Mechanisms Pocketbook

Reactions of Aromatic Compounds Images
Image gallery for study with links to larger teaching JPEGs for classroom presentation

Question Drill for Reactions of Aromatic Compounds
Conceptual Vocabulary Self-Test

Basic Terms Crossword Puzzle

Basic Puzzle Solution

Conceptual Vocabulary
Electrophilic aromatic substitutionElectrophilic aromatic substitution is an organic reaction in which an atom, usually hydrogen, appended to an aromatic system is replaced by an electrophile.
Ortho-substitutionOrtho-substitution is the arene susbstitution pattern in which two substituents occupy positions next to each other, which may be numbered 1 and 2.
Meta-substitutionMeta-substitution is the arene susbstitution pattern in which the substituents occupy positions 1 and 3.
Para-substitutionPara-substitution is the arene susbstitution pattern in which the substituents occupy the opposite ends, positions 1 and 4.
NitrationNitration occurs with aromatic organic compounds via an electrophilic aromatic substitution mechanism involving the attack of the electron-rich benzene ring by the nitronium ion.
Electrophilic halogenationElectrophilic aromatic halogenation is a type of electrophilic aromatic substitution in which a halide subsituent is added to an aromatic system.
Nucleophilic aromatic substitutionNucleophilic aromatic substitution is a reaction in which the nucleophile displaces a good leaving group, such as a halide on an aromatic ring.
Aromatic sulfonationAromatic sulfonation is an organic reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid functional group through electrophilic aromatic substitution.
AcylationAcylation is the process of adding an acyl group to a compound, which may occur in electrophilic aromatic substitution via the Friedel-Crafts mechanism.
AryneAn aryne is an uncharged reactive intermediate derived from an aromatic system by removal of two ortho substituents, which leaves two orbitals with two electrons distributed between them
Meisenheimer complexA Meisenheimer complex is a 1:1 reaction adduct between an arene carrying electron withdrawing groups and nucleophile. These are found as reactive intermediates in nucleophilic aromatic substitution, but stable and isolated Meisenheimer salts are also known.
Radical-nucleophilic aromatic substitutionRadical-nucleophilic aromatic substitution is a type of substitution reaction in which a certain substituent on an aromatic compound is replaced by a nucleophile through an intermediary free radical species.
Gattermann-Koch reactionThe Gattermann-Koch reaction refers to a Friedel-Crafts acylation reaction in which carbon monoxide and hydrochloric acid are used in-situ with Friedel-Crafts catalyst to produce a benzaldehyde-derivative in one step.
Gattermann reactionThe Gattermann rection refers to a reaction of hydrocyanic acid with an aromatic compound under catalysis of the Friedel-Crafts catalyst, aluminium chloride.
Advanced terms that may appear in context in MCAT passages
Sandmeyer reactionThe Sandmeyer reaction is used to synthesize aryl halides from aryl diazonium salts.
Scholl reactionThe Scholl reaction is a coupling reaction between two arene compounds with the aid of a Lewis acid and a protic acid.
Vilsmeier-Haack reactionThe Vilsmeier-Haack reaction is the chemical reaction of a substituted amide with phosphorus oxychloride and an activated arene to produce an aryl aldehyde or ketone.
Kolbe-Schmitt reactionThe Kolbe-Schmitt reaction is a carboxylation chemical reaction that proceeds by heating sodium phenolate with carbon dioxide under pressure, then treating the product with sulfuric acid to produce salicylic acid, the precursor to aspirin.
Pechmann condensationThe Pechmann condensation is a synthesis of coumarins, starting from a phenol and a carboxylic acid or ester containing a beta-carbonyl group.

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