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Richard F. Daley and Sally J. Daley
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Organic
Chemistry
Chapter 1

Atoms, Orbitals, and Bonds
1.1 The Periodic Table 21 1.2 Atomic Structure 22 1.3 Energy Levels and Atomic Orbitals 1.4 How Electrons Fill Orbitals 27 1.5 Bond Formation 28 1.6 Molecular Orbitals 30 1.7 Orbital Hybridization 35 1.8 Multiple Bonding 46 1.9 Drawing Lewis Structures 49 1.10 Polar Covalent Bonds 54 1.11 Inductive Effects on Bond Polarity 1.12 Formal Charges 58 1.13 Resonance 60 Key Ideas from Chapter 1 66 23

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Organic Chemistry - Ch 1

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Daley & Daley

Copyright 1996-2005 by Richard F. Daley & Sally J. Daley All Rights Reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, or otherwise, without the prior written permission of the copyright holder.

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5 July 2005

Organic Chemistry - Ch 1

19

Daley & Daley

Chapter 1

Atoms, Orbitals, and Bonds
Chapter Outline
1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 1.9 The Periodic Table
A review of the periodic table

Atomic Structure
Subatomic particles and isotopes

Energy Levels and Atomic Orbitals
A review of the energy levels and formation of atomic orbitals

How Electrons Fill Orbitals
The Pauli Exclusion principle and Aufbau principle

Bond Formation
An introduction to the various types of bonds

Molecular Orbitals
Formation of molecular orbitals from the 1s atomic orbitals of hydrogen

Orbital Hybridization
The VSEPR model and the three-dimensional geometry of molecules

Multiple Bonding
The formation of more than one molecular orbital between a pair of atoms

Drawing Lewis Structures
Drawing structures showing the arrangement of atoms, bonds, and nonbonding pairs of electrons

1.10 1.11 1.12 1.13

Polar Covalent Bonds
Polarity of bonds and bond dipoles

Inductive Effects on Bond Polarity
An introduction to how inductive and field effects affect bond polarity

Formal Charges
Finding the atom or atoms in a molecule that bear a charge

Resonance
An introduction to resonance

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5 July 2005

Organic Chemistry - Ch 1

20

Daley & Daley

Objectives
✔ Know how to use the periodic table ✔ Understand atomic structure of an atom including its mass number, isotopes, and orbitals ✔ Know how atomic orbitals overlap to form molecular orbitals ✔ Understand orbital hybridization ✔ Using the VSEPR model, predict the geometry of molecules ✔ Understand the formation of π molecular orbitals ✔ Know how to draw Lewis structures ✔ Predict the direction and approximate strength of a bond dipole ✔ Using a Lewis structure, find any atom or atoms in a molecule that has a formal charge ✔ Understand how to draw resonance structures

Concern for man and his fate must always form the chief interest of all technical endeavors. Never forget this in the midst of your diagrams and equations. —Albert Einstein

o comprehend bonding and molecular geometry in organic molecules, you must understand the electron configuration of individual atoms. This configuration includes the distribution of electrons into different energy levels and the arrangement of electrons into atomic orbitals. Also, you must understand the rearrangement of the atomic orbitals into hybrid orbitals. Such an understanding is important, because hybrid orbitals usually acquire a structure different from that of simple atomic orbitals. When an atomic orbital of one atom combines with an atomic orbital of another atom, they form a new orbital that bonds the two atoms into a molecule. Chemists call this new orbital a molecular orbital. A molecular orbital involves either the sharing of two electrons between two atoms or the transfer of one electron from one atom to another. You also need to know what factors affect the electron distribution in molecular orbitals to create polar bonds. These

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