Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 3, Problem 3.5P
Interpretation Introduction

Interpretation:

The hybrid orbital that will result from the interaction shown is to be derived. Whether the resulting orbital will be different from the ones shown in Figures 3-9a and 3-9b is to be determined.

Concept introduction:

Orbitals from the same atom can mix to form two or more hybrid orbitals. The number of hybrid orbitals formed is the same as the number of orbitals that mix. When an s and a p orbital mix, they form two hybrid orbitals, oriented at 180°. An s orbital has the same phase everywhere. A p orbital, on the other hand, has different phases in the two lobes. Therefore, when an s and a p orbitals mix, they produce hybrid orbitals with unequal lobes. Mixing of the lobe with the same sign as the s orbital leads to constructive interference, increasing the size of the lobe. The other lobe of p orbital has an opposite phase; therefore, its mixing leads to destructive interference on that side. The size of the lobe on this side is smaller than the other lobe. The other hybrid orbital is formed by overlap of the s orbital with the p orbital of reversed phases.

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Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. Select to Edit Arrows H H Select to Add Arrows > H CFCI: Select to Edit Arrows H Select to Edit Arrows
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