Photochemical Cycloaddition ([2+2])

2 CH₂=CH₂ → Cyclobutane

Visão geral

UV light promotes one alkene to its excited state, allowing a symmetry-forbidden [2+2] cycloaddition that cannot occur thermally according to the Woodward–Hoffmann rules. The product is a cyclobutane ring. This is a textbook example of how photochemistry enables reactions impossible by thermal pathways.

Participantes

Papel	Substância	Coeficiente	Estado
Reagente	Ethylene C₂H₄	2	(g)

Exemplo do cotidiano

UV-induced [2+2] cycloaddition between adjacent thymine bases in DNA creates cyclobutane pyrimidine dimers, the main cause of sunburn.

Importância industrial

A fotocicloadição [2+2] é utilizada em síntese orgânica para construir sistemas de anéis tensos e na síntese de produtos naturais e fármacos.

Propriedades

Tipo: Photochemical
Reversível: Não
Energia: Exotérmico
ΔH: -109,0 kJ/mol

Reações relacionadas

Photochemical Smog Formation (NO₂ Photolysis) Photochromism of Spiropyran Chlorophyll Fluorescence Photodegradation of Methylene Blue by TiO₂ Photodissociation of Chlorine Gas Silver Bromide Photodecomposition Cis-Trans Isomerization of Retinal Photosynthesis Ozone Formation by UV Light Dye-Sensitized Solar Cell (Grätzel Cell)

Frequently Asked Questions

What is the equation for Photochemical Cycloaddition ([2+2])?

The balanced equation is: 2 CH₂=CH₂ → Cyclobutane.

What type of reaction is Photochemical Cycloaddition ([2+2])?

Photochemical Cycloaddition ([2+2]) is a photochemical reaction.

Is Photochemical Cycloaddition ([2+2]) exothermic or endothermic?

Photochemical Cycloaddition ([2+2]) is exothermic (releases energy). The enthalpy change (ΔH) is -109.0 kJ/mol.