Diels-Alder Reaction (Butadiene + Ethylene)
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C4H6 + C2H4 → C6H10
Обзор
A conjugated diene (1,3-butadiene) reacts with a dienophile (ethylene) in a [4+2] cycloaddition to form cyclohexene. This pericyclic reaction proceeds through a concerted mechanism with no intermediates, forming two new carbon-carbon bonds and a six-membered ring simultaneously.
Участники
| Роль | Вещество | Коэффициент | Состояние |
|---|---|---|---|
| Реагент | Ethylene C₂H₄ | 1 | (g) |
| Продукт | Cyclohexane C₆H₁₂ | 1 | (l) |
Пример из жизни
Otto Diels and Kurt Alder won the 1950 Nobel Prize for discovering this reaction, which is taught in every organic chemistry course.
Промышленное значение
Diels-Alder reactions are used to synthesize steroids, terpenes, alkaloids, and many pharmaceutical intermediates with precise stereochemical control.
Свойства
- Тип
- Organic
- Обратимая
- Да
- Энергия
- Экзотермическая
- ΔH
- -40,0 kJ/mol