Кето-енольная таутомерия

[Ruepol]

Здравствуйте! Почему у ацетилацетона содержание енольной формы намного больше, чем у ацетона? Как это связано со второй карбонильной группой? Она электронакцептор, но как это влияет на стабильность этой формы? Заранее спасибо

[yatcheh]

Здравствуйте! Почему у ацетилацетона содержание енольной формы намного больше, чем у ацетона? Как это связано со второй карбонильной группой? Она электронакцептор, но как это влияет на стабильность этой формы? Заранее спасибо

 

Главная роль второго карбонила в ацетилацетоне - это образование внутримолекулярной водородной связи, стабилизирующей енольную форму:

 

 

Открытая, или трансоидная форма енола вообще не обнаруживается.

 

Второй по значению фактор стабилизации - сопряжение С=С связи енола с С=О связью карбонила. 

И только третий фактор - повышение С-Н кислотности кетонной формы из-за индуктивного влияния второго карбонила.

[George1royak]

Ответ в Кето-енольная таутомерия - Форум химиков на XuMuK.ru

 

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