Asked by Rijul Tuteja on May 26, 2024
Verified
In a Diels-Alder reaction, what is the endo rule?
Endo Rule
A guideline in Diels-Alder reactions predicting that the endo product is preferred for thermodynamic or kinetic reasons.
Diels-Alder
A synthetic chemical reaction between a conjugated diene and a substituted alkene, known as the dienophile, to form a cyclic product.
- Master the core tenets of the Diels-Alder reaction, particularly its regioselective characteristics and the implication of the endo rule.
Verified Answer
SE
Samantha EnciniaMay 28, 2024
Final Answer :
When the dienophile has a pi bond in its electron-withdrawing group (as in a carbonyl group or a cyano group), the p orbitals in that electron-withdrawing group approach one of the central carbon atoms (C2 or C3) of the diene. This proximity results in secondary overlap: an overlap of the p orbitals of the electron-withdrawing group with the p orbitals of C2 and C3 of the diene. Secondary overlap helps to stabilize the transition state. The unsaturated substituent on the dienophile generally prefers the endo position in the transition state, giving rise to the endo product in bicyclic systems.
Learning Objectives
- Master the core tenets of the Diels-Alder reaction, particularly its regioselective characteristics and the implication of the endo rule.
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