Basic Organic

Basic Chemistry

Petroleum Paraffins, Olefins,

Naphthenes and
Chemistry Aromatics
Chemistry of Crude Oil
PRT 190
Refinery Applications of
Introduction to Petroleum
Inorganic Chemistry
Refining
 BASIC ORGANIC
CHEMISTRY

Introduction to Petroleum Refining

 Organic Chemistry

study of the properties,

structures and reactions
of compounds of carbon
(that could be obtained
from living organisms)

Introduction to Petroleum Refining

 Carbon

food clothes

cosmetics plastics

gasoline

Introduction to Petroleum Refining

 Allotropes of Carbon

Amorphous Diamond

Graphite Fullerene

Introduction to Petroleum Refining

Introduction to Petroleum Refining
 Properties of Carbon

• has an affinity for bonding with small atoms

• capable of forming long C-C carbon chains (catenation)

• solid even at high temperatures

• does not react with hydrochloric acid, sulfuric acid or chlorine

Introduction to Petroleum Refining

 Occurrence of Carbon
• Atmosphere as Carbon dioxide

• Biosphere as biomass

• Hydrosphere as dissolved Carbon dioxide

• Lithosphere as carbonates and hydrocarbons

Introduction to Petroleum Refining

 The Carbon Atom
• Atomic Number = 6
• Average Atomic Mass = 12.011 amu
• Valence = 4
energy

2px 2py 2pz

2s2

1s2

Introduction to Petroleum Refining

 The Carbon Atom

2px 2py 2pz

2s2

1s2

2s 2px 2py

Introduction to Petroleum Refining

 Simple Carbon Compounds

Introduction to Petroleum Refining

 Atomic Orbitals
• Atomic Orbital - region in space in which the
probability of finding an electron is high

• Hybridization - involves the combination of

atomic orbitals to form hybrid orbitals
Introduction to Petroleum Refining
 sp3 Hybridization
Ground State Excited State sp3-Hybridzed State

2p 2p

2s 2s 2sp3

1s 1s 1s

Promotion of Electron Hybridization

Introduction to Petroleum Refining

 sp3 Hybridization

Methane, CH4

Introduction to Petroleum Refining

 sp2 Hybridization
Ground State Excited State sp2-Hybridzed State

2p 2p 2p

2s 2s 2sp2

1s 1s 1s

Promotion of Electron Hybridization

Introduction to Petroleum Refining

 sp2 Hybridization

Ethene, C2H4

Introduction to Petroleum Refining

 sp Hybridization
Ground State Excited State sp2-Hybridzed State

2p 2p 2p

2s 2s 2sp

1s 1s 1s

Promotion of Electron Hybridization

Introduction to Petroleum Refining

 sp Hybridization

Ethyne, C2H2

Introduction to Petroleum Refining

 Sigma and Pi Bonds
Sigma Bond

• electrons are shared between atoms

• the overlap region lies directly between the two
nuclei

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 Sigma and Pi Bonds
Pi Bond

• involve the electrons in the leftover p orbital for each

carbon atom
• the p orbitals are the electron clouds or orbitals that are
shown going up above and below each carbon atom

Introduction to Petroleum Refining

 Resonance
• Arises when there are more than one ways to
! draw a structure that satisfies the Octet Rule

• Used when there is more than one way to

! place double bonds and lone pairs on atoms

Introduction to Petroleum Refining

 The Aromatic Ring
Aromatic Compounds

• have low hydrogen to carbon ratio

• fragrant
• contain a six-carbon unit, which is retained
through most chemical transformations and
degradations
• parent compound is benzene

Introduction to Petroleum Refining

 Conjugation and Product Color
• Benzene Structure
Benzene’s carbons alternate
single (sigma) and double
(sigma + pi) bonds.

The delocalization of electrons

in the p orbitals associated
with the double bonds
explains benzene’s molecular
structure — the electrons are
not forced to bond on the
internuclear axis; they are free
to associate with one another
above and below the ring’s
plane.
Introduction to Petroleum Refining
 Conjugation and Product Color
Conjugation

• the presence of a p orbital on an atom

adjacent to a double bond (molecules
with delocalized  bond)
• causes the special properties of these
molecules (i.e., stability)
• allows molecules to absorb energy in the
ultraviolet and visible regions of the
electromagnetic spectrum

Introduction to Petroleum Refining

 Conjugation and Product Color

Conjugation

Introduction to Petroleum Refining

 Conjugation and Product Color

Introduction to Petroleum Refining

 Conjugation and Product Color
Excited State
Energy

Excited State

Ground State Ground State

Non conjugated System Conjugated System

Molecules having more conjugated multiple bonds

absorb lower energies of light than do molecules having
fewer conjugated multiple bonds.
Introduction to Petroleum Refining
 Conjugation and Product Color
• What may happen when light strikes an object?
• All wavelengths of the light may be reflected from the
1 surface (white)

• All wavelengths may be entirely absorbed by the object

2 (black)

• The light may be completely transmitted through the

3 object with little interaction (colorless)

• Some wavelengths can be reflected and others absorbed

4 (different colors)

Introduction to Petroleum Refining

 Conjugation and Product Color

When portions of light is absorbed, the remaining

portions are reflected (complementary color).

When the violet portion is absorbed, yellow is observed.

Introduction to Petroleum Refining

 Conjugation and Product Color

Introduction to Petroleum Refining