Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 1, Problem 49P
Interpretation Introduction

Interpretation:Hybridization scheme that gives best description of the carbons marked by asterisks and types of orbitals are used in these bonds should be identified. Whether the bond is expected to be stronger or weaker than an ordinary CC bond should be ascertained as well.

  Organic Chemistry: Structure and Function, Chapter 1, Problem 49P

Concept introduction: [2.2.2]propellane belong to class of hydrocarbons called propellane. This unstable compound has three rings composed of four carbon atoms. The bond angles are considerably strained.

In accordance with VSEPR model, if four bonds are present around the central atom the hybridization associated is sp3 and theses four orbitals tend to stay as far as 109.5 ° from one another so as to have minimum repulsions.

Similarly, if three bonds are present around the central atom the hybridization associated is sp2 and theses orbitals tend to stay as far as 120 ° from one another so as to have minimum repulsions.

The table that relates the hybridization with bond angles is as follows:

  Type of HybridisationBond anglesp180 °sp2120 °sp3109.5 °sp3d90 °,120 °,180 °sp3d290 °,180 °

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