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Chapter 30: Q39E (page 1033)

The following reaction is an example of a [2,3] sigmatropic rearrangement. Would you expect the reaction to be suprafacial or antarafacial? Explain.

Short Answer

Expert verified

A [2,3] sigmatropic rearrangement involves three electron pairs (one 蟺 bond, one lone pair, and one 蟽 bond), the orbital-symmetry rules predict a suprafacial reaction

Step by step solution

01

Orbital-symmetry rules

A [2,3] sigmatropic rearrangement involves three electron pairs (one 蟺 bond, one lone pair, and one 蟽 bond), the orbital-symmetry rules predict a suprafacial reaction.

According to the rules

Electron pairs (double bonds)

Thermal reaction

Photochemical reaction

Even number

Antarafacial

Suprafacial

Odd number

Suprafacial

Antarafacial

02

Mechanism

The mechanism for [2,3] sigmatropic rearrangement is shown as:

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