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Organic Chemistry

& 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.

This new energy level diagram is draw


below

This shows four open orbitals, allowing for


the formation of four bonds. Linus won a
noble prize for this theory. When carbon
atoms are bonded using all single bonds the
below shape forms from the combination of
one s orbital and three p orbitals. This
hybridization is named sp3. These shapes
are verified by an analysis technique named
X-Ray Crystallography. The compound is
frozen then photographed with X-Rays. The
resulting pictures have show this tetrahedral
shape.
In this instance the carbon atom forms
bonds with 4 different objects, resulting in a
tetrahedral shape, is shown above picture.
This shape is formed by the repulsion of the
electrons which surround all atoms. So, if
four objects are connected to a central
object the farthest these objects can be from
each other forms a tetrahedral shape. The
angle between these bonds is 109.5. The
blue balloon looking objects represent the
orbitals where the four electrons in carbons
second energy level reside. This is the
hybridization. Each of the four electrons
have equal energy and are all in the same
orbitals, they have been moved to the same
Shell instead of having the 2s electrons
located inside or underneath the 2p
electrons.
This tetrahedral shape has also been
verified by calculus. The addition of one
sphere and three dumbbell shapes produces
this tetrahedral shape.

General Properties of Organic


Molecules:
1.
2.
3.
4.
5.
6.
7.
8.
9.

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

Where n represents the number of carbons


and 2n+2 equals the number of hydrogens.

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.

The suffix for the alkane family is ane.

prefix root suffix


prefix where the substitutions are located
root how many carbons are in the
molecules longest chain
suffix family type of functional group
(alkane, alkene, alcohol, ester, etc...)
Root words are named for its number of
carbons:
# of carbons
root
1
meth2
eth3
prop4
but5
pent6
hex7
hept8
oct9
non10
decExample:
an alkane with 3 carbons is named propane
prop for the 3 carbons
ane for the family alkane (meaning all
single bonds)

Chemical Formula:
C4H10

Condensed Structural Formula:


CH3CH2CH2CH3

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

Side Chain Rules:


4-propyloctane

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

Chemical Equivalence non-isomers:


When one first begins learning how to name organic compounds they typically have a difficult
time recognizing when two molecules are actually the same molecule. Depending on how the
structural formula is drawn, the same molecule may look different to the novice. Lets look at
the following two structural formulas:
H H
F H
F

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.

Modifications of Straight Chained Alkanes: Cracking


Hydrocarbons are indeed flammable, but as it turns out this is not enough to make a fuel a
good fuel. An important characteristic for fuels made up of different chemicals, like the mixture
named gasoline, is that all the fuels ignite at the same time. If some fuel ignites before it is
designed to ignite undesirable result occur. This phenomenon in your conventional internal
combustion engine is called Engine Knock. The effects of engine knocking vary, some
symptoms include; unpleasant sounds, poor fuel economy, poor engine performance or even
engine damage.
The timing of ignition is very important. Many processes are occurring in concert with each
other to deliver smooth power to the cars wheels. Pistons are rising then being forced down by
the explosion of these hydrocarbon vapors mixed with oxygen gas from the atmosphere. The
idea is to detonate this mixture, with a spark plug in gasoline engines, when the piston has
reached the top of the chamber, as the fuel explodes the piston is forced down, this downward
motion is mechanically converted to rotating motion and transferred to the wheels.
The knock occurs when some of the fuel enters the cylinder and ignites before the spark plug
has fired. This causes the piston to apply force to the parts in the motor at that are not designed
to accept this force, at this time. The reason for the premature ignition is due to the varied
flammability of the different hydrocarbons found in gasoline. Some hydrocarbons fire simply
because they find themselves in a hot cylinder, and ignite before the spark plug sparks.
You have no doubt seen the different flavors of gasoline available at any gas station. Normally
octane numbers 87, 89 and 92 are available. The higher the number the less chance of
knocking. The alkane heptanes is considered the worst and is assigned an octane number of 0.
2,2,4-trimethylpentane, common name isooctane, earns an octane number of 100.

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

C3H8(g) + O2(g) CO2(g) + CO(g) + H2O(g) + less heat


incomplete occurs in low oxygen environments

Halogenation:
C3H8(g) + Br2(l) uv C3H7Br (g) + HBr(g)
Dehydrogenation:
C3H8(g) Pt C3H6(g) + H2(g)

Organic Functional Groups:


Organic molecules can be very complex, not only for their ability to branch off but also for
specialized groupings of atom each of which give molecules special properties. Most any of
these groupings, named organic functional groups, can attach themselves to any organic
molecule in most any location. One molecule may have more than one of these groups giving
the molecule different properties. In our studies of Organic Chemistry the reactivity of these
functional groups will a main focus.

Another Classification for Carbons:

primary carbon is bonded to one other carbon:


o both of these carbons
H H
H C

H H

secondary carbon is bonded to two other carbons:


o the center red carbon only
H H H
H C

H H H

tertiary carbon is bonded to three other carbons:


o the center red carbon only
H
H C

H C

H H H

quaternary carbon is bonded to four other carbons


o the center red carbon only
H
H C

H C

H C

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