Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 30.SE, Problem 28AP
Interpretation Introduction

Interpretation:

The product of the pericyclic reaction shown is to be predicted indicating whether the shift is a [5,5] suprafacial or an antrafacial process.

Concept introduction:

Sigmatropic rearrangements involve the migration of a σ bond present at the end or in the middle of the system across the π electron system from one position to another. They are represented by [m,n] where m and n represents the number of atoms between the bond being broken and the bond being formed in two directions.

If even number of electron pair is involved then thermal reaction occur through antarafacial pathway and photochemical reactions occur through suprafacial pathway.

If odd number of electron pair is involved then thermal reaction occur through suprafacial pathway and photochemical reactions occur through antarafacial pathway.

To predict:

The product of the pericyclic reaction shown indicating whether the shift is a [5,5] suprafacial or an antrafacial process.

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Consider this step in a radical reaction: Br N O hv What type of step is this? Check all that apply. Draw the products of the step on the right-hand side of the drawing area below. If more than one set of products is possible, draw any set. Also, draw the mechanism arrows on the left-hand side of the drawing area to show how this happens. O primary Otermination O initialization O electrophilic O none of the above × ☑
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Can I get a drawing of what is happening with the orbitals (particularly the p orbital) on the O in the OH group?  Is the p orbital on the O involved in the ring resonance?  Why or why not?
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