作者volley (生涯第一支全壘打)
看板Chemistry
標題Re: Epoxide的各種反應
時間Wed Jan 18 09:41:09 2006
※ 引述《wgs (我需要超級機械可魯)》之銘言:
: 請問各位神人
: CH3
: ∣ CH3OH
: CH3C——CH2 -----------------> ?
: \╱ ∣ H﹢ ----------------
: O ∣
: ∣
: ∣ CH3ONa
: ∣----------------> ?
: CH3OH ----------------
: 請問這兩者不同的酸是如何開環加成的
: 我有考慮到二級碳一級碳的問題 可是想不出所以然
: 有高手知道嗎
As treating this epoxide with proton in MeOH, protonation occurs
to generate the epoxide-proton cation, which could be regard as
the equivalent of alpha-hydroxy tertiary carbon cation...
thus the methanol addition takes place on the tertiary carbon to
form the alpha-hydroxyl ether.
but to deal the epoxide with sodium methoxide, no elimination will
happen because non of the protons of epoxide would be trapped by
methoxide anion.
Based on this, no reaction will undergo but nucleophilic attack.
the less steric hindered carbon attacked by methoxide resulted in
ring opening to form another kind of alpha-hydroxyl ether.
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