Organic Chemistry

Refinery and tank storage facilities, like this one in Texas,

are needed to change the hydrocarbons of crude oil to many
different petroleum products. The classes and properties of
hydrocarbons form one topic of study in organic chemistry.

Organic Compounds

An organic compound is one that has carbon as the

principal element

An inorganic element is any compound that is not

an organic compound.

Carbon is unique

t has ! electrons in its outer shell arranges "s

#
#s
#
sp
#

t has room for $ bonds to $ other atoms.

%rganic compounds ha&e specific geometry around

the carbon to carbon bond.

f there are four atoms or groups around a carbon atom, it

has a tetrahedral geometry.

'A(The carbon atom forms

bonds in a tetrahedral
structure )ith a bond angle
of "*+.,
%
. '-( Carbon.to.
carbon bond angles are
"*+.,
%
, so a chain of carbon
atoms makes a /ig/ag
pattern. 'C( The unbranched
chain of carbon atoms is
usually simplified in a )ay
that looks like a straight
chain, but it is actually a
/ig/ag, as sho)n in '-(.

Hydrocarbons

ntroduction

A hydrocarbon is a compound consisting of only

hydrogen and carbon.

The carbon to carbon can be single, double, or triple

bonds.

The bonds are al)ays nonpolar.

Alkanes are hydrocarbons )ith only single bonds.

Alkanes occur in )hat is called a homologous series.

0ach successi&e compound differs from the one before it only

by a C1
#

Carbon.to.carbon bonds can be

single 'A(, double '-(, or triple
'C(. 2ote that in each example,
each carbon atom has four
dashes, )hich represent four
bonding pairs of electrons,
satisfying the octet rule.

Carbon.to.carbon chains can be

'A( straight, '-( branched, or
'C( in a closed ring. '3ome
carbon bonds are dra)n longer,
but are actually the same
length.(

Compounds that ha&e the same molecular formula, but

different structures 'arrangements of the atoms( are
called isomers.

Naming alkanes

dentify the longest continuous chain.

The locations or other groups of atoms attached to the

longest chain are identified and numbered by counting
from the end of the molecule )hich keeps the
numbering system as lo) as possible.

1ydrocarbon groups that are attached to the longest

continuous chain and named using the parent name
and changing the ane suffix to yl.

Recall that a molecular

formula 'A( describes
the numbers of
different kinds of atoms
in a molecule, and a
structural formula '-(
represents a t)o.
dimensional model of
ho) the atoms are
bonded to each other.
0ach dash represents a
bonding pair of
electrons.

'A(A straight.chain
alkane is identified by
the prefix n. for
4normal4 in the
common naming
system. '-( A
branched.chain alkane
isomer is identified by
the prefix iso. for
4isomer4 in the
common naming
system. n the 56AC
name, isobutane is #.
methylpropane.
'Carbon bonds are
actually the same
length.(

Alkenes and Alkynes

Alkenes are hydrocarbons )ith at least one double

carbon to carbon bond.

To sho) the presence of the double bond, the ane

suffix from the alkane name is changed to ene.

The alkenes are unsaturated )ith respect to hydrogen

This means it does not ha&e the maximum number of

hydrogen atoms as it )ould if it )ere an alkane 'a
saturated hydrocarbon(.

0thylene is the gas that ripens fruit, and a ripe fruit emits the
gas, )hich )ill act on unripe fruit. Thus, a ripe tomato
placed in a sealed bag )ith green tomatoes )ill help ripen
them.

2aming is similar to naming alkanes except7

The longest continuous chain must contain the double

bond.

The base name no) ends in ene.

The carbons are numbered so as to keep the number

for the double bond as lo) as possible.

The base name is gi&en a number )hich identifies the

location of the double bond.

An alkyne is a hydrocarbon )ith at least one carbon to

carbon triple bond.

2aming an alkyne is similar to the alkenes, except the

base name ends in yne.

Cycloalkanes and Aromatic 1ydrocarbons

Cycloalkanes are alkanes 'only carbon to carbon single

bonds( )hich form a ring structure.

An aromatic compound is one that is based on the

ben/ene ring.

A benzene ring that is attached to another compound is

gi&en the name phenyl.

'A(The 4straight4 chain has

carbon atoms that are able to
rotate freely around their
single bonds, sometimes
linking up in a closed ring.
'-( Ring compounds of the
first four cycloalkanes.
'A(The bonds in C
!
1
!
are
something bet)een single
and double, )hich gi&es it
different chemical
properties than double.
bonded hydrocarbons. '-(
The six.sided symbol )ith
a circle represents the
ben/ene ring. %rganic
compounds based on the
ben/ene ring are called
aromatic hydrocarbons
because of their aromatic
character.

Petroleum

Petroleum is a mixture of alkanes, cycloalkanes,

and aromatic hydrocarbons.

6etroleum is formed from the slo) decomposition of

buried marine life, primarily plankton and algae.

As petroleum is formed it is forced through porous

rock until it reaches an imper&ious layer of rock.

1ere it forms an accumulation of petroleum and saturated

the porous rock creating an oil field.

6etroleum )as once used for medicinal purposes.

t )as first distilled by running through a )hiskey still, in

an attempt to make it taste better.

The liquid that he obtained burned quite )ell in lamps.

This clear liquid that )as obtained from petroleum

distillation )as called kerosene.

Crude oil is the petroleum that is pumped directly

from the ground.

t is a complex mixture of hydrocarbons )ith one or t)o

carbon atoms up to a limit of about ,* carbon atoms.

This is usually not useful, so it must separated by

distillation.

Crude oil from the ground is separated into usable groups of

hydrocarbons at this 8ouisiana refinery. 0ach petroleum
product has a boiling point range, or 4cut,4 of distilled
&apors that collect in condensing to)ers.

6etroleum
products and
the ranges of
hydrocarbons
in each
product.

The octane rating

scale is a
description of ho)
rapidly gasoline
burns. t is based
on 'A( n.heptane,
)ith an assigned
octane number of
*, and '-( #,#,$.
trimethylpentane,
)ith an assigned
number of "**.

Hydrocarbon Derivatives

ntroduction

1ydrocarbon deri&ati&es are formed )hen one or more

hydrogen atoms is replaced by an element or a group of
elements other than hydrogen.
Halogens '9
#
, Cl
#
, -r
#
,
#
,( can all add to a hydrocarbon
to form am alkyl halide.

:hen naming the halogen the ine ending is replaced by o

9luorine becomes fluoro

Chlorine becomes chloro

-romine becomes bromo

odine becomes iodo

Common examples of organic halides.

Alkenes can also add to each other in an addition reaction

to form long chains of carbon compounds.

this is called polymeri/ation

The atom or group of atoms that are added to the

hydrocarbon are called functional groups.

9unctional groups usually ha&e multiple bonds or lone

pairs of electrons that make them &ery reacti&e.

Alcohols

An alcohol has a hydrogen replaced by a hydroyl '.%1(

group.

The name of the hydrocarbon that )as substituted determines

the name of the alcohol.

The alcohol is named using the hydrocarbon name and adding

the suffix ol.

f methane is substituted )ith an %1 group it becomes

methanol

f a pentane group is substituted )ith an %1 group it is

pentanol.

9or alcohols )ith more than t)o carbon atoms )e need the
number the chain so as to keep the alcohol group as lo) as
possible.

9our different alcohols. The

56AC name is gi&en abo&e each
structural formula, and the
common name is gi&en belo).
;asoline is a mixture of hydrocarbons 'C
<
1
"<
for example(
that contain no atoms of oxygen. ;asohol contains ethyl
alcohol, C
#
1
,
%1, )hich does contain oxygen. The addition
of alcohol to gasoline, therefore, adds oxygen to the fuel.
3ince carbon monoxide forms )hen there is an insufficient
supply of oxygen, the addition of alcohol to gasoline helps
cut do)n on carbon monoxide emissions. An atmospheric
in&ersion, )ith increased air pollution, is likely during the
dates sho)n on the pump, so that is )hen the ethanol is
added.

The %1 group is polar and short chain alcohols are

soluble in both nonpolar alkanes and )ater.

f an alcohol contains t)o %1 groups it is a diol

'sometimes called a glycol(.

An alcohol )ith three %1 groups is called a triol

'sometimes called a glycerol(.

Common
examples of
alcohols )ith one,
t)o, and three
hydroxyl groups
per molecule. The
56AC name is
gi&en abo&e each
structural
formula, and the
common name is
gi&en belo).

!thers" Aldehydes" and #etones

An ether has a general formula R%R=

>iethyl ether for example )ould ha&e the formula

C1
?
C1
#
%C1
#
C1
?

An aldehyde has a carbonyl group 'carbon double

bonded to an oxygen( attached to a terminal carbon atom

A ketone has a carbonyl group attached to an internal

carbon atom.

The carbonyl group 'A( is

present in both aldehydes
and ketones, as sho)n in
'-(. 'C( The simplest
example of each, )ith the
56AC name abo&e and
the common name belo)
each formula.

Organic Acids and !sters

Organic acids are those acids that are deri&ed from

li&ing organisms, usually from metabolism, but
sometimes as a defense mechanism.

8ong chain organic acids are kno)n as fatty acids.

These are also called carboxylic acids as they contain the

carboxyl functional group 'C%%1(

%ne oxygen is double bonded to the carbon and the other is

bonded to the carbon and to the hydrogen both )ith single
bonds.

!sters are condensation products of carboxylic acids

)ith the remo&al of )ater 'also called a dehydration
synthesis(.

These red ants, like other ants, make the simplest of the
organic acids, formic acid. The sting of bees, ants, and some
plants contains formic acid, along )ith some other irritating
materials. 9ormic acid is 1C%%1.

Organic Compounds of $ife

ntroduction

8i&ing organisms ha&e to be able to7

0xchange matter and energy )ith their surroundings.

Transform matter and energy into different forms.

Respond to changes in their en&ironment.

;ro).

Reproduce.

All of these changes are due to large organic compounds

called macromolecules.

A macromolecule is a combination of many smaller similar

molecules polymeri/ed into a chain structure.

n li&ing organisms there are three main types of

macromolecules )hich control all acti&ities and
determine )hat an organism )ill do and become.

6roteins.

Carbohydrates

2ucleic acids.

The basic unit of life is the cell.

The cell makes up all li&ing organisms that )e kno) of.

Cells are in turn made of macromolecules that form inside the

cell.

%ther macromolecules control the formation of these

macromolecules.

%etabolism is the breaking do)n or building up of

macromolecules.

;enerally, breaking do)n macromolecules releases energy that

the organism can use as an energy source.

The building up of macromolecules requires energy, that is

obtained from breaking do)n macromolecules.

Proteins

6roteins are macromolecules that are polymers of amino

acids.

&tructurally, proteins go into making muscle tissue,

connecti&e tissue, and skin, hair, and nails, @ust to name a
fe).

'unctionally proteins are en/ymes )hich cataly/e

biochemical reactions

-uilding up macromolecules requires energy and an en/yme

lo)ers the amount of energy that is necessary.

There are #* amino acids that go into producing proteins.

These amino acids are polymeri/ed by a dehydration

synthesis to form long chains of repeating amino acids
called a protein.

The arrangement of the amino acids in the polymer

determine the structure of the protein )hich confers to
it is function or structural attributes.

The t)enty amino

acids that make up
proteins, )ith three.
letter abbre&iations.
The carboxyl group
of one amino acid
bonds )ith the amino
group of a second
acid to yield a
dipeptide and )ater.
6roteins are
polypeptides.

6art of a protein polypeptide made up of the amino acids

cysteine 'cys(, &aline '&al(, and lysine 'lys(. A protein can
ha&e from fifty to one thousand of these amino acid unitsA
each protein has its o)n unique sequence.

Carbohydrates

Carbohydrates are a large group of compounds that are

generally called sugars, starches, and cellulose 'all of
)hich are sugars or polymers of sugars(

;enerally sugars are a storage source of energy.

-y breaking sugars do)n into carbon dioxide and )ater, li&ing

organisms can release the energy that is locked up in them to
use for energy requirements.

(lucose is the carbohydrate that animals utili/e mostly

for their energy.

;lucose 'blood sugar( is an aldehyde, and fructose 'fruit

sugar( is a ketone. -oth ha&e a molecular formula of C
!
1
"#
%
!

Classification

A monosaccharide is one that is made up of @ust one

sugar unit.

A disaccharide is one that is made up of t)o sugar

units.

A polysaccharide is one that is made up of many

sugar units.

These plants and their flo)ers

are made up of a mixture of
carbohydrates that )ere
manufactured from carbon
dioxide and )ater, )ith the
energy of sunlight. The simplest
of the carbohydrates are the
monosaccharides, simple sugars
'fruit sugar( that the plant
synthesi/es. 9ood is stored as
starches, )hich are
polysaccharides made from the
simpler monosaccharides. The
plant structure is held upright by
fibers of cellulose, another form
of a polysaccharide.

&tarch is a storage carbohydrate used by plants.

:hen plants photosynthesi/e the use the energy from

sunlight to con&ert carbon dioxide and )ater into
sugars and oxygen.

(lycogen is a storage carbohydrate used by animals.

Cellulose is a polysaccharide that is used in plant cell

)alls to maintain their structure.

3tarch and cellulose are both polymers of glucose, but

humans cannot digest cellulose. The difference in the
bonding arrangement might seem minor, but en/ymes must
fit a molecule &ery precisely. Thus, en/ymes that break
do)n starch do nothing to cellulose.

'ats and Oils

1umans take in amino acids and utili/e them to

synthesi/e the polymers that are called proteins.

There are "* amino acids )hich humans cannot

synthesi/e themsel&es and must be in the diet, these
are called essential amino acids.

1umans also take in carbohydrates and use the break

do)n of the carbohydrate as an energy source.

:hen either of these is taken in in quantities abo&e that

that is necessary for the body, they are con&erted into fats
in animals and oils in plants.

9ats and oils are a long term storage for energy

sources.

Animal fats are )ither saturated or unsaturated, but most

are saturated.

5nsaturated fats are belie&ed to lo)er cholesterol

le&els in humans.

3aturated fats and cholesterol are thought to contribute

to hardening of the arteries.

9ats are stored in adipose tissue )hich has an insulating

function, a padding 'protecti&e( function, as )ell as a
storage function.

The triglyceride
structure of fats and
oils. 2ote the glycerol
structure on the left
and the ester structure
on the right. Also
notice that R", R#,
and R? are long.
chained molecules of
"#, "$, "!, "<, #*, ##,
or #$ carbons that
might be saturated or
unsaturated.

&ynthetic Polymers

Polymers

6olymers are long molecules )ith repeating structures of

simpler molecules.

3ynthetic
polymers,
the
polymer
unit, and
some uses
of each
polymer.

6etroleum and coal

as sources of ra)
materials for
manufacturing
synthetic polymers.
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