作者volley (生涯第一支全垒打)
看板Chemistry
标题Re: Epoxide的各种反应
时间Wed Jan 18 09:41:09 2006
※ 引述《wgs (我需要超级机械可鲁)》之铭言:
: 请问各位神人
: CH3
: ∣ CH3OH
: CH3C——CH2 -----------------> ?
: \╱ ∣ H﹢ ----------------
: O ∣
: ∣
: ∣ CH3ONa
: ∣----------------> ?
: CH3OH ----------------
: 请问这两者不同的酸是如何开环加成的
: 我有考虑到二级碳一级碳的问题 可是想不出所以然
: 有高手知道吗
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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