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Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Non è quello che usi tu?Cambia libro di testo
Capitolo 19, Problema 22g

What are the products of the following reactions?
g.

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Step 1: Identify the reactants. The first reactant is pyrrole, a five-membered aromatic ring containing nitrogen. The second reactant is a diazonium salt, specifically benzenediazonium ion (C₆H₅N⁺≡N).
Step 2: Recognize the type of reaction. This is an electrophilic substitution reaction where the diazonium ion acts as an electrophile and reacts with the pyrrole ring.
Step 3: Determine the site of attack. Pyrrole is highly reactive due to its aromaticity and electron-rich nature. The nitrogen atom contributes electron density to the ring, making the 2-position (adjacent to nitrogen) the most reactive site for electrophilic substitution.
Step 4: Predict the intermediate. The diazonium ion will attack the 2-position of pyrrole, forming a sigma complex (arenium ion) as an intermediate. This intermediate will then lose a proton to restore aromaticity.
Step 5: Write the product structure. The final product will be a 2-aryl pyrrole, where the phenyl group (C₆H₅) is attached to the 2-position of the pyrrole ring.

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Reaction Mechanisms

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Functional Groups

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