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& Alkanes
Hybridization:
The 4 bonds carbon forms is explained by
Linus Paulings theory of hybridization.
Carbon atoms have an electron
configuration of 1s2 2s2 2p2 This
configuration corresponds to the following
energy level diagram.
2p
2s
1s
From the looks of this diagram, carbon might
form 3 bonds as appears to be nowhere for
a 4th bond to form. Linus theorized that the
two sublevels, s and p, in the second energy
level formed a hybrid sublevel.
Flammable
High Vapor Pressure
Odorous
Covalently Bonded
Non-Polar functional groups can
change these from non-polar to polar or
cause the molecule to be bi-polar.
Low Solubility in Water due to being
non-polar as water is polar
Rate of Chemical Reaction is Normally
Slow
Normally Found as Gasses and Liquids
at Room Temp
Non-Conductive of Electrical Current
Alkanes:
The first classification for organic molecules
is the most simple, the alkanet. The most
simple alkanet consists of only carbon and
hydrogen atoms connected by single bonds.
Alkanes are common and for the most part
chemically uncreative, the chemical
reaction combustion being the major
exception.
Alkanes can be found in many common
substances; natural gas, gasoline, plastics
The chemical formula can be generalized
as:
CnH2n+2
Nomenclature:
Nomenclature is the scientific term for
naming compounds. The governing body is
The International Union of Pure and Applied
Chemistry, or IUPAC for short. The
following statement is from their web site:
The International Union of Pure and Applied
Chemistry (IUPAC) serves to advance the
worldwide aspects of the chemical sciences
and to contribute to the application of
chemistry in the service of Mankind. As a
scientific, international, non-governmental
and objective body, IUPAC can address
many global issues involving the chemical
sciences.
IUPAC was formed in 1919 by chemists
from industry and academia. One of there
main functions is to objectively create rules
for naming compounds in the most simplified
manner possible. This is equivalent to
creating a new language, just like English
grammar, there are rules.
Even with the advent and acceptance of the
IUPAC system some common names still
persist, when discussing a substance the
IUPAC name should be used but the
common name will be accepted by most
chemical organizations.
Alkane Nomenclature:
Naming of organic structures, unlike
biological classification, follows a rigid set of
rules. The International Union of Pure and
Applied Chemistry, abbreviated IUPAC,
came up with a set of rules that follows the
same standards worldwide, and is accepted
among all chemists. However, common
names of compounds, or names that have
historical roots, are still used today for many
compounds.
Chemical Formula:
C4H10
Structural Formula:
H H H H
H C
C C
Line Structure:
H
H H H H
Rules:
1. Find the longest chain of carbons, and use this number as the base/root/parent name
2. Number the chain with the end nearest the first subsistent carbon #1.
3. Give the location of the alkyl subsistent by the number of the main-chain carbon that it is
attached to.
4. Put the Constituents in alphabetical order (i.e. ethyl before methyl)
5. Substitution Syntax:
a. between numbers and words add a dash
b. between numbers add commas
4-ethyl-octane
Correct
5-ethyl-octane
Incorrect
4-ethyl-2-methylheptane
Correct
4-ethyl-6-methylheptane
Incorrect
2-methyl-4-ethylheptane
Incorrect
4-isoproplyoctane
CH2CH2CH3
CH3CHCH3
CH3CH2CH2CH2CHCH2CH2CH3
CH3CH2CH2CH2CHCH2CH2CH3
5-butylnonane
5-secbutylnonane
CH2CH2CH2CH3
CH3CH2CH2CH2CHCH2CH2CH2CH3
5-isobutylnonane
CH3 CHCH2CH3
CH3CH2CH2CH2CHCH2CH2CH2CH3
5-tertbutylnonane
CH3
CH CH3
CH2
CH3CH2CH2CH2CHCH2CH2CH2CH3
CH3
CH3
C CH3
CH3CH2CH2CH2CHCH2CH2CH2CH3
Isomers:
Isomerization - same molecular formula, but different structure. Also creates different properties
for the molecule. The number of possible isomers increases rapidly as the length of the chain
increases. These molecules are isomers of the same chemical formula.
Each of the following molecules has a chemical formula of C 4H10 but they are different molecules
having different properties.
butane
2-methyl propane (isobutane)
hexane
2-methyl pentane
3-methyl pentane
2,2-dimethyl butane
C C H
H C C H
H H
H H
These two molecules look different but they are actually the same. Single bonds are unique in
that the atoms on each side of the bond can rotate or spin around the bond. So, the difference
between the two above molecules is simply that the carbon-carbon bond is rotated to a different
position. At all times the fluorine and two hydrogens will be spinning about the carbon.
Lets look a this molecule a little more, by the way, its name is fluoroethane. And the reason we
do not have to say 1-fluoroethane is because no matter which carbon we put the fluorine on,
that carbon will be carbon #1. The following structural drawings will all actually be of this same
molecule:
H H
F
C C H
H C C H
H H
H C C H
H H
H H
H H
H F
H H
H C C F
H C C H
H C C H
H H
H H
H F
Yes, they look different, try using a molecular modeling kit and proving to yourself that yes
indeed, these are all the same. You will learn that you do not have to pull any of the atoms off to
have your model look like each structure above. You simply twist the carbon-carbon bond or flip
the molecule around.
Now lets talk about a new molecule, 1,2-difluoroethane. I just added another fluorine to our
fluoroethane molecule.
H H
F
C C F
H H
These two fluorine atoms are said to be chemically equivalent. This means that both fluorines
will react, chemically, in exactly the same manner. To recognize you look at the carbon that the
fluorine is bonded to. Both fluorines have the exact same description, the fluorines are bonded
to a carbon that is singly bonded to another carbon and also bonded to two other hydrogens.
Since both fluorines fit this description they are chemically equivalent.
If we look at the hydrogens on this molecule we can demonstrate that they too are all chemically
equivalent. Each hydrogen fits this description, a hydrogen bonded to a carbon, the carbon is
singly bonded to another hydrogen, a fluorine and another hydrogen.
Looking back to the fluoroethane we can see that not all of the hydrogens are chemically
equivalent. On carbon #1, there is one fluorine and two hydrogens, on carbon #2 there are only
three hydrogens.
The following molecules have two colored atoms, these colored atoms are listed as either
chemically equivalent or non-equivalent.
Cl H
nonF C C F
equivalent
H H
F H H H
H C C C C F
H H H H
Br
Br
equivalent
nonequivalent
The easiest way to recognize chemical equivalence, is to look for symmetry. If the two atoms
you are comparing have symmetry between themselves on the molecule, they are probably
chemically equivalent.
Cyclic Alkanes:
Alkanes can form compounds with themselves. By this I mean they commonly form rings.
Shown below is cyclohexane. It is a hexane molecule that has come around back onto itself.
The below you will find the chemical formula, structural formula and the line diagram.
H
H
H
H
C
C H
H C
H C
C H
C
H
H HH
C6H12
Sources of Alkanes:
Crude oil is the main supplier. Crude oil is gently heated in a tower, this heating produces
vapors, the lighter compounds to rise higher in the tower, while the heavier compounds rise
very little. Collection equipment is stationed at various levels ready to remove hydrocarbons of
various masses. Alkanes tend to be light and very non-polar, thus they travel to the top of the
tower. Natural gas is the name given to the lightest of the alkanes, this gas is a combination of
methane, ethane and propane. Natural gas pockets are found above large deposits of crude oil.
See picture of refinement tower below.
Alkanes can also be made these synthetically in a lab, like Professor Whler, in 1828 made
urea. But his process is time consuming and expensive. Verify this yourself by pricing synthetic
motor oil verse regular motor oil. Synthetic can easily be 15 times more expensive.
2,2,4-trimethylpentane
So, the more isooctane the higher the octane number and the less likely you will have a knock
occur. The more branching the better the fuel. Catalytic cracking, breaks apart straight chained
alkanes, then catalytic reforming reforms the bonds, as branched hydrocarbons. The above
isooctane could have been octane cracked and reformed as isooctane. The branching gives the
molecule increase stability. Is allows it to withstand higher temperatures as it waits to be ignited
by the firing spark plug. Aromatics, compound containing benzene rings, are also desirable
hydrocarbons due to their high stability.
Reactions of Alkane:
Combustion:
C3H8(g) + O2(g) CO2(g) + H2O(g) + heat
complete occurs in high oxygen environments
Halogenation:
C3H8(g) + Br2(l) uv C3H7Br (g) + HBr(g)
Dehydrogenation:
C3H8(g) Pt C3H6(g) + H2(g)
H H
H H H
H C
H H H
H C
H C