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Francesca Beltran
Chem 31
Elementary Organic Chemistry
Prerequisite: Chem 16
T303
Consultation Hours
! TWThF: 2-5PM
! francescabeltran@gmail.com
Schedule of Exams
1st LE: Jan 8
2nd LE: Feb 12
3rd LE: Mar 21
Structure and Bonding

Based from McMurrys Organic
Chemistry, 7th edition
What is Organic Chemistry

Living things are made of organic chemicals
Proteins that make up hair
DNA, controls genetic make-up
Foods, medicines
Origins of Organic Chemistry

Foundations of organic chemistry from mid-1700s.
Compounds obtained from plants, animals are hard to
isolate, and purify.
Compounds also decomposed more easily.
Torben Bergman (1770) first to make distinction
between organic and inorganic chemistry.
It was thought that organic compounds must contain
some vital force because they were from living sources.
Origins of Organic Chemistry

Because of Vital force, it was thought that
organic compounds could not be synthesized in
laboratory like inorganic compounds.
1816, Chevreul
1828, Wohler
Atomic Structure
Structure of an atom
! Positively charged nucleus (very dense, protons and
neutrons) and small (10-15 m)
! Negatively charged electrons are in a cloud (10-10 m) around
nucleus
Atomic Number and Atomic Mass

The atomic number (Z) is the number of protons in the
atom's nucleus
The mass number (A) is the number of protons plus
neutrons
All the atoms of a given element have the same atomic
number
Isotopes are atoms of the same element that have
different numbers of neutrons and therefore different
mass numbers
The atomic mass (atomic weight) of an element is the
weighted average mass in atomic mass units (amu) of an
elements naturally occurring isotopes
Orbitals and Shells
Atomic Orbitals
Atomic orbitals are regions of space where the
probability of finding an electron about an atom
is highest.
Electronic Configuration
Chemical Bonding Theory

Kekul and Couper independently observed that
carbon always has four bonds
van't Hoff and Le Bel proposed that the four
bonds of carbon have specific spatial directions
Properties of a Covalent Bond

Shape of Molecules and Bond Angle
depends on the orientation or rearrangement
about the nucleus of the bonding orbitals of the
central atom
Chemical Bonding
Atoms form bonds because the compound that
results is more stable than the separate atoms
Ionic bonds in salts form as a result of electron
transfers
Organic compounds have covalent bonds from
sharing electrons (G. N. Lewis, 1916)

Bond Polarity consequence of the tendency
of a more electronegative atom to attract
electrons toward itself
Electronegativity : F > O > N, Cl > Br > C, H

Bond Length internuclear distance between
2 bonded atoms
The bigger the atoms, the longer the bond
length.
CH3 Cl < CH3 Br < CH3 - I

Bond Length internuclear distance between
2 bonded atoms
! The greater the no. of bonds or electron between
two atoms, the shorter the bond
single > double > triple

Bond Dissociation Energy energy needed
to break a bond; numerically equivalent to the
amount of energy liberated when the same bond
is broken
! The stronger the bond, the higher the BDE
single < double < triple
Lewis structures (electron dot) show valence electrons

of an atom as dots
Kekule structures (line-bond structures) have a line
drawn between two atoms indicating a 2 electron
covalent bond.
Stable molecule results at completed shell, octet (eight
dots) for main-group atoms (two for hydrogen)

Bond Dissociation Energy energy needed
to break a bond; numerically equivalent to the
amount of energy liberated when the same bond
is broken
! The shorter the bond, the higher the BDE
CH3 Cl > CH3 Br > CH3 - I
The Nature of Chemical Bonds

Valence Bond Theory
! Electrons are paired in the overlapping
orbitals and are attracted to nuclei of both
atoms
! HH bond results from the overlap of two singly

occupied hydrogen 1s orbitals
! H-H bond is cylindrically symmetrical, sigma (!)
bond
Bond Energy
Bond Length
sp3 Orbitals and the Structure of

Methane
The Structure of Methane

Each CH bond has a strength of 436 (438) kJ/
mol and length of 109 pm
Bond angle: each HCH is 109.5, the
tetrahedral angle.

Ethane

Ethylene
Bonds From sp2 Hybrid Orbitals
Structure of Ethylene
Two sp2-hybridized orbitals overlap to form a !

bond
p orbitals overlap side-to-side to formation a pi
(") bond
sp2sp2 ! bond and 2p2p " bond result in
sharing four electrons and formation of C-C
double bond
sp Orbitals and the Structure of

Acetylene
Orbitals of Acetylene
Bonding in Acetylene
Hybridization of Nitrogen and Oxygen
The Nature of Chemical Bonds

Molecular Orbital Theory
! A molecular orbital (MO): where electrons
are most likely to be found (specific energy and
general shape) in a molecule
Molecular Orbitals in Ethylene
Noncovalent Interactions
Dispersion forces
Dipole-dipole forces
Hydrogen bonding
Polarity of the Molecule
Map of Electrostatic Potential
Polar and Nonpolar Molecules
Polar and Nonpolar Molecules
Dispersion Forces
Dipole-Dipole
Occur between all neighboring molecules and

arise because the electron distribution within
molecules that are constantly changing
Occur between polar molecules as a result of

electrostatic interactions among dipoles
Forces can be attractive of repulsive depending
on orientation of the molecules
Hydrogen Bond Forces

Most important noncovalent interaction in
biological molecules
Drawing Structures
3 General Rules
1) Carbon atoms arent usually shown. Instead a
carbon atom is assumed to be at each
intersection of two lines (bonds) and at the end
of each line.
2) Hydrogen atoms bonded to carbon arent
shown.
3) Atoms other than carbon and hydrogen are
shown

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Francesca Beltran

Structure and Bonding

What is Organic Chemistry

Origins of Organic Chemistry

Origins of Organic Chemistry

Atomic Number and Atomic Mass

Orbitals and Shells

Chemical Bonding Theory

Properties of a Covalent Bond

Properties of a Covalent Bond

Properties of a Covalent Bond

Properties of a Covalent Bond

single > double > triple

Properties of a Covalent Bond

single < double < triple

Lewis structures (electron dot) show valence electrons

Properties of a Covalent Bond

CH3 Cl > CH3 Br > CH3 - I

The Nature of Chemical Bonds

! HH bond results from the overlap of two singly

sp3 Orbitals and the Structure of

The Structure of Methane

sp3 Orbitals and the Structure of

sp2 Orbitals and the Structure of

Bonds From sp2 Hybrid Orbitals

Two sp2-hybridized orbitals overlap to form a !

sp Orbitals and the Structure of

Hybridization of Nitrogen and Oxygen

The Nature of Chemical Bonds

Molecular Orbitals in Ethylene

Polarity of the Molecule

Map of Electrostatic Potential

Polar and Nonpolar Molecules

Polar and Nonpolar Molecules

Occur between all neighboring molecules and

Occur between polar molecules as a result of

Hydrogen Bond Forces

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