Cycloaddition reactions
Why is is that cis-1,3-butadiene and ethene react to form cyclohexene when heated:
(Diels-Alder
reaction, 4 +2 cycloaddition)
but the analogous cycloaddition of two ethene molecules
does not work?
(2+2
cycloaddition, calculated to be exothermic by 75 kJ/mol)
We can explain and understand this through the principles
of conservation of orbital symmetry