Chemistry Stack Exchange is a question and answer site for scientists, academics, teachers, and students in the field of chemistry. It only takes a minute to sign up.
Sign up to join this community
Are the mechanism and the product for this given reaction right or is there anything wrong with it? 1,2 - Epoxybutane has originally the 2R configuration and the product got an R configuration as well.
I was not sure about, where the nucleophile attacks. Under acidic conditions steric hindrance will be ignored, right? In this case the hydrogen atom will be added to the less substituted carbon atom and the ring will be opened.
The free electron pairs of the oxirane may act as a Lewis base and coordinate with a Lewis acid like $\ce{Li+}$. This form of activation facilitates the attack of the alanate $\ce{[AlH4]-}$ as a $\sigma$-nucleophile at the less substituted side of the epoxide.
Once opened, the nucleophilic oxygen attacks at the electron deficient centre of $\ce{AlH3}$ (Lewis acid). But the $\ce{Al-O}$ bond hydrolyzes upon the workup, yielding the alcohol and the hydroxides of lithium and aluminum.
