Five-Membered Heterocycles: Aromaticity and Reactivity Order
Organic Chemistry · Heterocycles Five-Membered Heterocycles: Aromaticity and Reactivity Order Three rings with the same shape and very different reactivity. The difference tracks one property of the heteroatom. BSc & MSc · Organic Chemistry · Concept The short answer: Pyrrole, furan and thiophene are all aromatic six-electron systems in which the heteroatom donates its lone pair to the ring. Their reactivity toward electrophiles follows the heteroatom’s willingness to share that pair, so pyrrole is most reactive and thiophene least among the three toward electrophilic attack. Why they are aromatic Each ring has two carbon–carbon double bonds, contributing four π electrons….