Solved: Furan undergoes electrophilic aromatic substitution more readily than benzene;
Chapter 0, Problem 17-57(choose chapter or problem)
Furan undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient. For example, furan reacts with bromine to give 2-bromofuran. (a) Propose mechanisms for the bromination of furan at the 2-position and at the 3-position. Draw the resonance forms of each sigma complex, and compare their stabilities. (b) Explain why furan undergoes bromination (and other electrophilic aromatic substitutions) primarily at the 2-position.
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