🥼organic chemistry review

Sigmatropic rearrangement

Written by the Fiveable Content Team • Last updated August 2025
Written by the Fiveable Content Team • Last updated August 2025

Definition

Sigmatropic rearrangement is a type of pericyclic reaction in organic chemistry where a sigma bond (σ-bond) adjacent to a pi system (π-system) migrates from one position to another, simultaneously affecting the positions of π-electrons. This migration is guided by specific orbital symmetries that allow the reaction to proceed without the need for external reagents.

AP course connection

Topic 27.5: 27.5 Terpenoids

Unit 27
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