INTRODUCTION TO ORGANIC CHEMISTRY

●​ Dated mid-1700s; alchemists tried to

explain differences between compounds
derived from living and non-living
●​ Torbern Bergman: expressed the
difference between organic and inorganic.
●​ Jons Jacob Berzelius: coined the term
organic chemistry to express the chemistry
of compounds from living organisms and Valence Electrons
compounds made by humans such as ●​ Each element from Groups 1 to 8 have
plastics, pharmaceuticals, eic. electron(s) on their outermost shell. These
Atomic Structure electrons are called valence electrons.
●​ The number of electrons is determined by
their group number (i.e., Group I elements
have one electron, group 2 have 2, and so
on, until 8)
●​ Of these groups, only group & elements are
non-reactive under normal circumstances,
while the rest are reactive
The Periodic Table of Elements

Valence Electrons and the Octet Rule

●​ Why are noble gases generally non-reactive
under normal circumstances?
●​ Because they have a stable electron
configuration; that is, the number of
electrons on their valence shell is at full
capacity which is 8.
●​ When elements have a full number of
electrons in their valence shell, they have
Atomic Weight vs. Atomic Mass satisfied the octet rule.
●​ Atomic mass is the sum of protons and ●​ In the formation of a chemical bond, these
neutrons of a single atom. electrons are either shared or transferred to
●​ Atomic weight is the weighted average of satisfy this rule: main-group elements tend
the atomic mass of all natural isotopes of an to bond in such a way that each atom has
element. eight electrons in its valence shell, making
its electron configuration the same as that of
noble gases.
 ●​ Covalent chemical bonds involve the
sharing of a pair of valence electrons by two
atoms, in contrast to the transfer of
electrons in ionic bonds.
●​ Covalent bonds lead to stable molecules if
they share electrons in such a way as to
Lewis Theory, the Octet Rule, and Atomic create a noble gas configuration (octet:
Bonding ns2np6) for each atom.
●​ Lewis Theory: a structural depiction that
obeys the octet rule and, using a set of rules
that takes into account the number of
electrons to satisfy the octet rule (N) and the
number of electrons available, is used to
predict the number of electrons to be
shared.
Elements of the theory:
-​ Valence electrons play a fundamental role in -​ Hydrogen gas (H2) forms the simplest
chemical bonding. covalent bond in the diatomic hydrogen
●​ Ionic bonding involves the transfer of one molecule.
or more electrons from one atom to another.
●​ Covalent bonding involves sharing Lone Pairs:
electrons between atoms. ●​ Since hydrogen has only one electron in its
-​ Electrons are transferred or shared such valence, it satisfies the octet rule with a
that each atom gains an electron duet.
configuration of a noble gas (ns"np%). i.e. ●​ When other covalent species form, there
having 8 outer shell (valence) electrons. are additional electron pairs ¡hat do not.
-​ This arrangement is called the octet rule. participate in bonding. These are called
-​ Exceptions to the octet rule do exist and will "lone pairs" (lp)
be explored later.

●​ Lewis Symbols represent the resulting

structures that accommodate the octet rule.
In a Lewis symbol, an element is
surrounded by up to 8 dots, where
elemental symbol represents the nucleus
and the dots represent the valence Multiple bonds:
electrons. ●​ The oxygen and nitrogen that makes up the
bulk of the atmosphere also exhibits
covalent bonding in forming diatomic
molecules.
Polyatomic Molecules (More than two atoms) ●​ The Lewis structure predicts the number of
●​ Carbon dioxide: CO2 valence electron pairs around the central
atom(s).
●​ Each lone pair of electrons constitutes one
electron group on a central atom.
●​ Each bond constitutes one electron group
on a central atom, regardless of whether it
is single, double, or triple.

Electron Groups and Molecular Geometry

Molecular Structure and Properties
●​ Properties of molecular substances depend
Two Electron Groups: Linear
on the structure of the molecule.
Geometry
●​ Structure include many factors
●​ When there are two electron groups around
-​ Arrangement of the atoms
the central atom, they will occupy positions
-​ Type of bonding between atoms (ionic, polar
on opposite sides of the central atom.
covalent, covalent)
●​ This results in the electron groups taking a
-​ Shape of the molecule
linear geometry.
●​ Valence Shell Electron Pair Repulsion
●​ The bond angle is 180°
Theory (VSEPR Theory) allow us to predict
shapes of molecules based on molecular
geometry (orientation of atoms in space)

Lewis Theory and Electron Groups

●​ Lewis theory also predicts there are
regions of electrons in an atom.
-​ Some regions result from placing shared
pairs of valence electrons between bonding Three Electron Groups: Trigonal Planar
nuclei Geometry
-​ Other regions result from placing unshared ●​ When there are three electron groups
valence electrons on a single nuclei. around the central atom, they will occupy
●​ Lewis theory: regions of electron groups positions in the shape of a triangle around
should repel each other, because they are the central atom.
regions of negative charge ●​ This results in the electron groups taking a
-​ Can be extended to predict the shapes of trigonal planar geometry.
the molecules ●​ The bond angle is 120°.
-​ The position of atoms surrounding a central
atom will be determined by where the
bonding electron groups are.
-​ The positions of the electron groups will be
determined by trying to minimize repulsions
between them.
 in the shape of two square base pyramids
Four Electron Groups: Tetrahedral Electron that are base-lo-base with the central atom
Geometry in the center of the shared bases.
●​ When there are four electron groups around ●​ This results in the electron groups taking an
the central atom. they will occupy positions octahedral geometry. It is called
in the shape of a tetrahedron around the octahedral because the geometric figure
central atom. has eight sides.
●​ This results in the electron groups taking a ●​ All positions are equivalent.
tetrahedral geometry. ●​ The bond angle is 90°.
●​ The bond angle is 109.5°

Five Electron Groups: Trigonal Bipyramidal

Not Quite Perfect Geometry
●​ When there are live electron groups around
●​ The actual geometry of the molecule may
the central alom, they will occupy positions
be different from the electron geometry.
in the shape of two tetrahedral that are base
●​ When the electron groups are attached to
lo base with ihe central atom in the center of
atoms of different size, or when the bonding
the shared bases.
to one atom is different than the bonding to
●​ This results in the electron groups taking a
another, this will affect the molecular
trigonal bi-pyramidal geometry.
geometry around the central atom.
●​ The positions above and below the central
●​ Lone pairs also affect the molecular
atom are called the axial positions.
geometry. They occupy space on the central
●​ The positions in the same base plane as the
atom but are not "seen" as points on the
central atom are called the equatorial
molecular geometry.
positions. The bond angle between
equatorial positions is 120°.
●​ The bond angle between axial and
equatorial positions is 90°

Six Electron Groups: Octahedral Electron -​ Because the bonds and atom sizes are
Geometry not identical in formaldehyde, the
●​ When there are six electron groups around observed angles are slightly different
the central atom, they will occupy positions from ideal.
Effects of Lone Pair
●​ Lone pair groups "occupy more space" on Electron Configuration and Valence Bond
the central atom because their electron Theory
density is exclusively on the central atom,
rather than shared like bonding electron Electrons: The Key to Chemical Reactions
groups.
●​ Relative sizes of repulsive force interactions
is as follows:

Lone Pair - Lone Pair > Lone Pair - Bonding Pair

> Bonding Pair - Bonding Pair

●​ This affects the bond angles, making the

bonding pair angles smaller than expected.

Electron Configuration
●​ Atomic orbitals: regions in the atom where
electrons are most likely found.
●​ Each atomic orbital has four subshells in
which there are four types: s, p, d, f. Each
subshell can only accommodate a number
of electrons.
●​ 0 S= 2, p = 6. d = 10. f = 14
 ●​ Remember: s= 2e, p = 6e, d = 10e, f =14e
-​ The electrons are even because they come
in identical pairs. Therefore, there is an odd
number of subshells per atomic orbital.
●​ The electron configuration can be written by
noting the atomic orbital (a number).
followed by the subshell (s, p, d, or l), and
filing these subshells with the total amount
of electrons of that element.

Valence Bond Theory

●​ In the formation of a bond, simple atomic
orbitals on the central atom "mix" to form
new "hybrid" orbitals. This process is known
as orbital hybridization.
●​ Take note: hybridization happens only on
the participating orbital.

Valence Bond Theory: Main Concepts

Electron Configuration and Valence Bond 1.​ The valence electrons of the atoms in a
Theory molecule reside in quantum-mechanical
●​ Principles of quantum mechanics were atomic orbitals. The orbitals can be the
applied by Linus Pauling to molecules. standard s, p, d, and f orbitals, or they may
●​ They reasoned that bonds between atoms be hybrid combinations of these.
would occur when the orbitals on those 2.​ A chemical bond results when these atomic
atoms interacted to make a bond. orbitals interact and there is a total of two
●​ The kind of interaction depends on whether electrons in the new molecular orbital
the orbitals align along the axis between the a.) The electrons must be spin paired.
nuclei, or outside the axis. 3.​ The shape of the molecule is determined by
●​ Describes how atomic orbitals form bonds the geometry of the interacting orbitals.
●​ A covalent bond is formed by the Orbital hybridization: sp3 hybridization
overlapping of two half-filled atomic orbitals ●​ Atom with four electron groups around it
of two atoms having electrons with opposite ●​ Tetrahedral geometry -109.5°angles
spin between hybrid orbitals
 ●​ Atom uses hybrid orbitals for all bonds and Orbital hybridization: sp hybridization
lone pairs ●​ Atom with two electron groups
●​ Single bonds formed are known as sigma ●​ Linear in shape, 180° bond angle
bonds (o bonds) ●​ Contains triple bond: one sigma, and two pi
bonds.

●​ 2s orbitals combine with one 2p (particularly

2px) orbital to form two sp hybrid orbitals.
2py and 2pz orbitals remain unhybridized.
●​ The two sp orbitals from each atom forms
●​ The four valence orbitals of the carbon and
the sigma bond, while the unhybridized 2py
nitrogen combine mathematically to form
and 2pz overlap to form the two pi bonds
our equivalent hybrid orbitals
●​ Called sp3 orbitals because it is made up of
ones orbital and three p orbitals
●​ Each of the four valence electrons on the
carbon occupies a single sp3 orbital

Orbital hybridization: sp2 hybridization Why Carbon?

●​ Molecule with three electron groups around ●​ Carbon, together with H, is present in all
it organic compounds.
Trigonal planar system ●​ Carbon is tetravalent.
C = Trigonal planar ●​ Carbon bond is not randomly oriented; they
N = Trigonal bent form tetrahedron.
O = Linear ●​ Carbon can bond to one another to form
●​ 120° degree bond angles, flat extended chains; chains can double back to
●​ Contains double bonds, in which one bond form rings
is a sigma bond, while the other is a pi ( )
bond BASIC CHEMICAL REACTIONS

Chemical Equations
●​ Representation of a chemical reaction
●​ Involves symbols and chemical formulas
Reading Chemical Equations

States of Matter based on Chemical

Reaction
●​ Physical state of a chemical can be
indicated by a letter in parenthesis
(s) is solid
(l) is liquid
(g) is gas
(aq) is aqueous solution, chemical is dissolved in
water