Conrotatory and disrotatory

This article includes a list of references, related reading, or external links, but its sources remain unclear because it lacks inline citations. Please help improve this article by introducing more precise citations. (April 2020) (Learn how and when to remove this message)

In organic chemistry, an electrocyclic reaction can either be classified as conrotatory or disrotatory based on the rotation at each end of the molecule. In conrotatory mode, both atomic orbitals of the end groups turn in the same direction (such as both atomic orbitals rotating clockwise or counter-clockwise). In disrotatory mode, the atomic orbitals of the end groups turn in opposite directions (one atomic orbital turns clockwise and the other counter-clockwise). The cis/trans geometry of the final product is directly decided by the difference between conrotation and disrotation.

Determining whether a particular reaction is conrotatory or disrotatory can be accomplished by examining the molecular orbitals of each molecule and through a set of rules. Only two pieces of information are required to determine conrotation or disrotation using the set of rules: how many electrons are in the pi-system and whether the reaction is induced by heat or by light. This set of rules can also be derived from an analysis of the molecular orbitals for predicting the stereochemistry of electrocyclic reactions.