Bondline / Reactions

Diels–Alder reaction

A diene and a dienophile join in one concerted step through a cyclic six-electron transition state, making a cyclohexene and two new C–C σ bonds.

Pericyclic · 1 step

Conditions

Heat. Electron-poor dienophiles (C=C–C=O, C=C–CN) react fastest; the diene must be s-cis.

Mechanism

Red curly arrows show where each pair of electrons moves.

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MechanismThree curly arrows move round the ring at the same time: two new σ bonds form and the remaining π bond shifts to the middle.

About pericyclic reactions

Pericyclic reactions happen in one step through a cyclic transition state, with electrons moving around a ring. No intermediates form.

Practise this mechanismDraw the curly arrows yourself and Bondline checks each one. Or add it to your notes and watch it in 3D.

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