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Chapter 12 :
Reactions of Arenes. Electrophilic Aromatic Substitution
Ch 12 contents

Electrophilic Aromatic Substitution of Heteroaromatics

The 5 membered heterocycles react in a similar way. As an example here is the general pattern for the electrophilic aromatic substitution reactivity of furan, complete with the 3 important resonance structures that justify the reactivity of the 2-position.

resonance structures for reaction of furan at the 2-position
electrophilic aromatic substitution of furan at the 2-position

QUESTION How many important resonance structures can you draw for reaction at the 3-position ? ANSWER

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organic chemistry © Dr. Ian Hunt, Department of Chemistry University of Calgary