Chapter 1

Remembering
General Chemistry:
Electronic Structure
and Bonding

Paula Yurkanis Bruice

University of California,
Santa Barbara
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What is Organic Chemistry?

Organic compounds: from living organisms
(with a vital force)
Inorganic compounds: from minerals
(with a vital force)

organic chemistry = compounds that contain carbon

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What Makes Carbon So Special?

Atoms to the left of carbon give up electrons.

Atoms to the right of carbon accept electrons.
Carbon shares electrons.
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The Structure of an Atom

Protons are positively charged.
Neutrons have no charge.
Electrons are negatively charged.
Atomic number = # of protons
Atomic number of carbon = 6
Neutral carbon has six protons
and six electrons.

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Isotopes

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The Distribution of Electrons in an Atom

The first shell is closest to the nucleus.

The closer the atomic orbital is to the
nucleus, the lower its energy.
Within a shell, s < p.
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Relative Energies of the Atomic Orbitals

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-Aufbau principle: An electron goes into the atomic orbital with

the lowest energy.
-Pauli exclusion principle: No more than two electrons can be
in an atomic orbital.
-Hunds rule: An electron goes into an empty degenerate
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orbital rather than pairing up.

Atoms on the Left Side of the

Periodic Table Lose an Electron

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Atoms on the Right Side of the

Periodic Table Gain an Electron

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A Hydrogen Atom Can Lose or

Gain an Electron

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An Ionic Bond is Formed by the Attraction

Between Ions of Opposite Charge

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Covalent Bonds are Formed by

Sharing Electrons

Nonpolar covalent bond = bonded atoms are the same

Polar covalent bond = bonded atoms are different

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How Many Bonds Does

an Atom Form?

Lewis Structures
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Bond Polarity Depends on

the Difference in Electronegativity

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Polar Covalent Bonds

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Dipole Moments

the greater the difference in electronegativity,

the greater the dipole moment, and the more polar the bond
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Electrostatic Potential Maps

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Formal Charge

Formal Charge = the number or valence electrons

1/2 the number of bonding electrons
or
Formal Charge = the number or valence electrons
the number of bonds

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Neutral Carbon Forms Four Bonds

if carbon does not form four bonds, it has a charge

(or it is a radical)

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Neutral Nitrogen Forms Three Bonds

Nitrogen has one lone pair.

If nitrogen does not form three bonds, it is charged.

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Neutral Oxygen Forms Two Bonds

Oxygen has two lone pairs.

If oxygen does not form two bonds, it is charged.

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Hydrogen and the Halogens

Form One Bond

A halogen has three lone pairs.

if hydrogen or halogen does not form one bond, it has a charge
(or it is a radical)

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The Number of Bonds and Lone Pairs

Halogen = 3 lone pairs

Oxygen = 2 lone pairs
Nitrogen = 1 lone pair
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Lewis Structures

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How to Draw a Lewis Structure

NO3
Determine the total number of valence electrons (5 + 6 + 6 + 6 = 23).
Because they are negatively charged, add another electron = 24.
Avoid OO bonds.
Check for formal charges.

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Kekul Structures and

Condensed Structures

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What is an Atomic Orbital?

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A Standing Wave

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The Lobes of a p Orbital Have

Opposite Phases

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The Three p Orbitals

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The Bonding in H2

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Waves Can Reinforce Each Other;

Waves Can Cancel Each Other

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Atomic Orbitals Combine

to Form Molecular Orbitals

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Side-to-Side Overlap of In-Phase

p Orbitals Forms a Bond

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The p Orbital of the More Electronegative

Atom Contributes More to the Bonding MO

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The Bonding in Methane

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In Order to Form Four Bonds,

Carbon Must Promote an Electron

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Four Orbitals are Mixed to Form

Four Hybrid Orbitals

An sp3 orbital has a large lobe and a small lobe.

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The Carbon in Methane is sp3

Carbon is tetrahedral.
The tetrahedral bond angle is 109.5.
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The Bonding in Ethane

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The Bonding in Ethane

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End-On Overlap of Orbitals

Forms a () Bond

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Bonding in Ethene

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An sp2 Carbon Has Three sp2 Orbitals

and One p Orbital

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The Carbons in Ethene are sp2

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Bonding in Ethyne

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The Two sp Orbitals Point in Opposite Directions

The Two p Orbitals are Perpendicular

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The Carbons in Ethyne are sp

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Methyl Cation and Methyl Radical are sp2

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Methyl Anion is sp3

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Nitrogen Has Three Unpaired Valence Electrons

and Forms Three Bonds in NH3

Nitrogen does not have to promote an electron.

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The Bonds in Ammonia (NH3)

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The Ammonium Ion (+NH4)

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Oxygen Has Two Unpaired Valence

Electrons and Forms Two Bonds in H2O

Oxygen does not have to promote an electron.

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The Bonds in Water (H2O)

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The Bond in a Hydrogen Halide

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Overlap of an s Orbital with an sp3 Orbital

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The Length and Strength of a

Hydrogen Halide Bond

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Summary of Hybridization

orbitals used in bond formation determine the bond angle

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Single Bond: 1 + 1

Double bond: 1 + 2

Triple Bond: 1 + 2

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Hybridization of C, N, and O

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Bond Strength and Bond Length

The shorter the bond, the stronger it is.

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s Character

The shorter the bond, the stronger it is.

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The More s Character in the Orbital,

the Shorter and Stronger the Bond

The more s character, the shorter and stronger the bond.

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The More s Character in the Orbital,

the Greater the Bond Angle

The more s character, the greater the bond angle.

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Hybridization, Bond Angle,

Bond Length, Bond Strength

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Summary
The shorter the bond, the stronger it is.
The greater the electron density in the region of orbital
overlap, the stronger the bond.
The more s character, the shorter and stronger the bond.
The more s character, the larger the bond angle.

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A Bond is Weaker Than a Bond

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Dipole Moments of Molecules

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Dipole Moments of Molecules

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