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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 22d

What are the products of the following reactions?
d.

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Step 1: Identify the reactants and reagents. The reactants are 2-methylfuran and acetyl chloride (CH3COCl). The reagents are BF3/THF followed by hydrolysis with H2O.
Step 2: Recognize the reaction type. This is an electrophilic aromatic substitution reaction where the furan ring acts as the nucleophile, and acetyl chloride provides the electrophile (acyl group). BF3 acts as a Lewis acid catalyst to facilitate the reaction.
Step 3: Determine the site of substitution. Furan is an aromatic heterocycle, and its electron-rich nature makes it highly reactive towards electrophilic substitution. The most reactive positions are the 2- and 5-positions of the furan ring due to resonance stabilization.
Step 4: Predict the intermediate. The acyl group (CH3CO-) will attach to the 2-position of the furan ring, forming an acylated intermediate. BF3 helps stabilize the transition state during this process.
Step 5: Hydrolysis step. After the acylation, the reaction mixture is treated with water (H2O), which ensures the removal of any remaining BF3 and stabilizes the final product. The final product is 2-acetyl-5-methylfuran.

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