Epoxidation of Alkenes (mCPBA)

R2C=CR2 + mCPBA → epoxide + mCBA

概述

Meta-chloroperoxybenzoic acid (mCPBA) converts alkenes to epoxides (oxiranes) in a concerted syn-addition. The peracid oxygen inserts into the C=C bond, forming a strained three-membered ring. Epoxides are highly reactive due to ring strain and serve as versatile synthetic intermediates.

日常示例

Epoxy resin adhesives (like Araldite) are made from epoxides that cross-link with hardeners to form incredibly strong bonds.

工业重要性

烯烃环氧化是有机合成中制备环氧化物的关键步骤，环氧化物可进一步开环制备反式二醇、氨基醇等功能分子。工业上采用多种环氧化方法：钛硅分子筛（TS-1）催化的过氧化氢环氧化用于生产环氧丙烷（绿色化学），夏普莱斯不对称环氧化用于手性药物合成（2001年诺贝尔化学奖）。

属性

类型
Organic
可逆
否
能量
放热
ΔH
-200.0 kJ/mol

相关反应

Swern Oxidation Oxidation of Secondary Alcohol to Ketone E2 Elimination (Dehydrohalogenation) Claisen Condensation (Ethyl Acetate) Aldol Condensation of Acetaldehyde Kolbe Electrolysis Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Catalytic Hydrogenation of Ethylene Dehydration of Ethanol

Frequently Asked Questions

What is the equation for Epoxidation of Alkenes (mCPBA)?
The balanced equation is: R₂C=CR₂ + mCPBA → epoxide + mCBA.
What type of reaction is Epoxidation of Alkenes (mCPBA)?
Epoxidation of Alkenes (mCPBA) is a organic reaction.
Is Epoxidation of Alkenes (mCPBA) exothermic or endothermic?
Epoxidation of Alkenes (mCPBA) is exothermic (releases energy). The enthalpy change (ΔH) is -200.0 kJ/mol.