An Overview of Organic

Reactions
 Development of Chemical Bonding Theory
Ionic compounds
• Some elements achieve an octet configuration by gaining or losing electrons
• Ions form when an electron is gained or lost from a neutral atom
• Ions are charged because they have different numbers of protons and
electrons
• Ions are held together by an electrostatic attraction, like in Na+ Cl-, forming an
ionic bond

Covalent compounds
• Covalent Bond
– Bond formed by sharing electrons between atoms
• Molecule
– Neutral collection of atoms held together by covalent bonds
• Carbon achieves an octet configuration by sharing electrons
 2.1 Polar Covalent Bonds: Electronegativity

Chemical bonds
• Ionic bonds
– Ions held together by electrostatic attractions between unlike
charges
– Bond in sodium chloride
• Sodium transfers an electron to chlorine to give Na+ and Cl-
• Nonpolar Covalent bonds
– Two electrons are shared equally by the two bonding atoms
– Carbon-carbon bond in ethane
• Symmetrical electron distribution in the bond

Most bonds are neither fully ionic or covalent

 Covalent Bonds are Formed by
Sharing Electrons Between Non-Metals

Nonpolar covalent bond = bonded atoms are the same

No difference in electronegativity between atoms

Polar covalent bond = bonded atoms differ in electronegativity

Non- Polar Covalent Bond
 Polar Covalent Bonds: Electronegativity

• Polar covalent bonds

– A covalent bond in which the electron distribution between atoms is
unsymmetrical

– Bond polarity is due to difference in electronegativity (EN)

Polar Covalent Bonds
 Polar Covalent Bonds: Electronegativity
Electronegativity (EN)
• The ability of an atom to attract shared electrons in a covalent
bond
• Generally increases across the periodic table from left to right and
from bottom to top
 Polar Covalent Bonds: Electronegativity
• Bonds between atoms whose electronegativities differ by less
than 0.5 are nonpolar covalent
• Bonds between atoms whose electronegativities differ by 0.5 to
2.0 are polar covalent
• Bonds between atoms whose electronegativities differ by more
than 2.0 are largely ionic

Carbon hydrogen bonds are nonpolar. Bonds between carbon (EN =

2.5) and more electronegative elements, such as oxygen (EN =
3.5) and nitrogen (EN = 3.0) are polar covalent bonds with the
bonding electrons drawn towards the more electronegative
atoms
Polar Covalent Bonds
 Organic Chemical Reactions
Organic chemical reactions broadly organized in
two ways:

1. What kinds of reactions occur

2. How those reactions occur

 Kinds of Organic Reactions
Addition reactions
• Occur when two reactants add together to form a single product with
no atoms “left over”
 Kinds of Organic Reactions
Elimination reactions
• Occur when a single reactant splits into two products (usually
with the formation of a small molecule such as water)
 Kinds of Organic Reactions
Substitution reactions
• Occur when two reactants exchange parts to give two new
products
 Kinds of Organic Reactions
Rearrangement reactions
• Occur when a single reactant undergoes a reorganization of
bonds and atoms to yield an isomeric product
 Learning Check:

What kind of reaction is the transformation shown below?

Cl
+ HCl

1. an elimination reaction
2. a rearrangement reaction
3. a substitution reaction
4. an addition reaction
5. none of these
 Solution:

What kind of reaction is the transformation shown below?

Cl
+ HCl

1. an elimination reaction
2. a rearrangement reaction
3. a substitution reaction
4. an addition reaction
5. none of these
 How Organic Reactions Occur: Mechanisms
Reaction Mechanism
• An overall description of how a reaction occurs at each stage of a
chemical transformation
– Which bonds are broken and in what order
– Which bonds are formed and in what order
– What is the relative rate of each step
• A complete mechanism accounts for all reactants consumed and
all products formed
 How Organic Reactions Occur: Mechanisms

All chemical reactions involve bond breaking and bond making

Two ways a covalent two-electron bond can break:

1. Symmetrical
• One electron remains
with each product
fragment Half-headed arrow, “fishhook”,
indicates movement of one
2. Unsymmetrical electron
• Both bonding electrons
remain with one
product fragment,
Full-headed arrow indicates
leaving the other with
movement of two electrons
a vacant orbital
 How Organic Reactions Occur: Mechanisms
Two ways a covalent two-electron bond can form:

1. Symmetrical
• One electron is donated to the
new bond by each reactant (radical)

2. Unsymmetrical
• Both bonding electrons are
donated by one reactant (polar)
 How Organic Reactions Occur: Mechanisms
Radical reaction
• Process that involves symmetrical bond breaking and bond
making
– Radical (free radical)
• A neutral chemical species that contains an odd number
of electrons and has a single, unpaired electron in one of
its orbitals
Polar reactions
• Process that involves unsymmetrical bond breaking and bond
making
– Involve species that have an even number of electrons (have
only electron pairs in their orbitals)
– Common in both organic and biological chemistry
 6.3 Radical Reactions
Radical
• Highly reactive because it contains an atom with an odd
number of electrons (usually seven) in a valence shell
• Can achieve a valence shell octet through:
– Radical substitution reaction
• Radical abstracts an atom and one bonding electron from
another reactant