The complete, detailed mechanism for the given reaction is to be drawn. It is to be explained why nucleophilic attack takes place predominantly at the epoxide carbon that is attached to the vinyl group. Concept introduction: Epoxides react readily under neutral, basic, and acidic reaction conditions. Under acidic conditions, a nucleophile attacks an epoxide at the more substituted carbon atom. When an epoxide is treated with a strong acid, the first step is the protonation of the oxygen atom in the epoxide ring, which is a proton-transfer step. The C − O bond in an epoxide partially breaks on protonation. As a result, both the carbon atoms develop a partial positive charge. In the second step, the nucleophile produced in the first step attacks the more substituted carbon atom or the carbon atom at which the positive charge is more stabilized through delocalization because the highly substituted or resonance stabilized carbon atom is more electrophilic and can accommodate a partial positive charge better that the less substituted carbon atom.

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Chapter 10, Problem 10.55P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn. It is to be explained why nucleophilic attack takes place predominantly at the epoxide carbon that is attached to the vinyl group.

Concept introduction:

Epoxides react readily under neutral, basic, and acidic reaction conditions. Under acidic conditions, a nucleophile attacks an epoxide at the more substituted carbon atom. When an epoxide is treated with a strong acid, the first step is the protonation of the oxygen atom in the epoxide ring, which is a proton-transfer step. The C−O bond in an epoxide partially breaks on protonation. As a result, both the carbon atoms develop a partial positive charge. In the second step, the nucleophile produced in the first step attacks the more substituted carbon atom or the carbon atom at which the positive charge is more stabilized through delocalization because the highly substituted or resonance stabilized carbon atom is more electrophilic and can accommodate a partial positive charge better that the less substituted carbon atom.

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