Question

Isoprene rule

Answer 1

[AI-generated answer — Bot GPT 3.5]

The isoprene rule, also known as the Bredt's rule or the Bredt-Jutzeler rule, states that a double bond cannot be placed at the bridgehead carbon atom of a bicyclic compound if it would result in a small ring. This rule is named after the chemists Julius Bredt and Adrien-Jean-Pierre Jutzeler.

The reason behind the isoprene rule is that placing a double bond at the bridgehead carbon atom of a small ring would require a high angle strain due to the restricted orientation of the substituents. This strain significantly destabilizes the molecule, making it highly reactive and prone to rearrangements.

The isoprene rule is often used in organic chemistry to predict the reactivity and stability of bicyclic compounds. It helps chemists determine the most favorable position for double bonds in these compounds to minimize strain and achieve greater stability.