Introduction to

Organic
Molecules and
Functional
Groups

Lecture # 04
Organic Chemistry

• Carbon is unique among the other elements in that its atoms can
form stable covalent bonds with each other and with atoms of other
elements in a multitude of variations.
• The resulting molecules can contain from one to millions of carbon
atoms.
 • Organic chemicals affect virtually every facet of our lives,
and for this reason, it is important and useful to know
something about them.
• Clothes, foods, medicines, gasoline, refrigerants, and soaps
are composed almost solely of organic molecules.
Organic • Some, like cotton, wool, or silk are naturally occurring; that
Chemistry is, they can be isolated directly from natural sources.
Others, such as nylon and polyester, are synthetic,
meaning they are produced by chemists in the laboratory.
• Our lives would be vastly different today without the many
products that result from organic chemistry.
 Some Representative
Organic Molecules
• Methane, the simplest of all organic compounds, contains one
carbon atom.
• Methane—the main component of natural gas—occurs widely in
nature. Methane is the product of the anaerobic (without air)
decomposition of organic matter by bacteria. The natural gas we use
today was formed by the decomposition of organic material millions
of years ago.

• Ethanol, the alcohol present in beer, wine, and other alcoholic

beverages, is formed by the fermentation of sugar, quite possibly the
oldest example of organic synthesis.
• Ethanol can also be made in the lab by a totally different process, but
the ethanol produced in the lab is identical to the ethanol produced
by fermentation.
• Trichlorofluoromethane is a member of a
class of molecules called
chlorofluorocarbons or CFCs, which
contain one or two carbon atoms and
several halogens.
• Trichlorofluoromethane is an unusual
organic molecule in that it contains no
hydrogen atoms.
• Because it has a low molecular weight and
is easily vaporized,
trichlorofluoromethane has been used as
an aerosol propellant and refrigerant.
• It and other CFCs have been implicated in
the destruction of the stratospheric ozone
layer.
 Shorthand to Draw Complex Organic
Compounds
• Because more complicated organic compounds
contain many carbon atoms, organic chemists
have devised a shorthand to draw them. Keep in
mind the following when examining these
structures:
✓ Each solid line represents a two-electron
covalent bond.
✓ When no atom is drawn at the corner of a ring,
an organic chemist assumes it to be carbon. For
example, in the six-membered ring drawn, there
is one carbon atom at each corner of the
hexagon.
Complex Organic Compounds

• Three complex organic molecules that are

important medications are amoxicillin, fluoxetine,
and AZT.
✓Amoxicillin is one of the most widely used
antibiotics in the penicillin family.
✓Fluoxetine is the generic name for the
antidepressant Prozac.
✓AZT, the abbreviation for azidodeoxythymidine, is
a drug that treats human immunodeficiency virus
(HIV), the virus that causes acquired immune
deficiency syndrome (AIDS).
• Other complex organic compounds
having interesting properties are
capsaicin and DDT.
• Capsaicin, one member of a group
of compounds called vanilloids, is
responsible for the characteristic
spiciness of hot peppers.

• DDT, the abbreviation for

dichlorodiphenyltrichloroethane, is a
pesticide once called“ miraculous” by
Winston Churchill because of the many
lives it saved by killing disease carrying
mosquitoes.

• DDT use is now banned in the United

States and many developed countries
because it is a nonspecific insecticide that
persists in the environment.
 • All organic compounds contain
carbon atoms and most contain
hydrogen atoms.
• All the carbon atoms have four These features explain why
bonds. A stable carbon atom is there are so many organic
Common said to be tetravalent. compounds: Carbon forms
• Other elements may also be four strong bonds with itself
Features of present. Any atom that is not
carbon or hydrogen is called a
and other elements. Carbon
atoms combine together to
Organic heteroatom.
• Common heteroatoms include N,
form rings and chains.

Compounds O, S, P, and the halogens.

• Some compounds have chains of
atoms and some compounds have
rings.

Organic chemistry
is the study of
carbon
Key Takeaway compounds, nearly
all of which also
contain hydrogen
atoms.
Characteristic Features of an Organic Compound
• Most organic molecules have C– C and C – H σ bonds. These bonds are strong, nonpolar, and
not readily broken. Organic molecules may have the following structural features as well:
• Heteroatoms—atoms other than carbon or hydrogen. Common heteroatoms are
nitrogen, oxygen, sulfur, phosphorus, and the halogens.
• pi Bonds. The most common π bonds occur in C – C and C – O double bonds.
• These structural features distinguish one organic molecule from another. They determine a
molecule’s geometry, physical properties, and reactivity, and comprise what is called a
functional group.
Why do heteroatoms and π bonds confer
reactivity on a particular molecule?
• Don’t think, though, that the C – C and C – H σ bonds are unimportant.
They form the carbon backbone or skeleton to which the functional
groups are bonded.
• A functional group usually behaves the same whether it is bonded to a
carbon skeleton having as few as two or as many as 20 carbons.
• For this reason, we often abbreviate the carbon and hydrogen portion of
the molecule by a capital letter R, and draw the R bonded to a particular
functional group.
 • Ethane, for example, has only C – C and C – H σ bonds, so it has no
functional group. Ethane has no polar bonds, no lone pairs, and no
π bonds, so it has no reactive sites. Because of this, ethane and

Examples: Ethane molecules like it are very unreactive.

& Ethanol • Ethanol, on the other hand, has two carbons and five hydrogens in
its carbon backbone, as well as an OH group, a functional group
called a hydroxy group. Ethanol has lone pairs and polar
bonds that make it reactive with a variety of reagents, including
the acids and bases.

Most organic compounds can be grouped into a relatively small number of categories, based on the structure of
their functional group. Ethane, for example, is an alkane, whereas ethanol is a simple alcohol.
An Overview of Functional Groups
Classification of • We can subdivide the most common functional groups
into three types.
Common 1. Hydrocarbons

Functional 2. Compounds containing a C – Z σ bond where Z = an

electronegative element

Groups 3. Compounds containing a C––O group

1. Hydrocarbons
• Hydrocarbons are compounds made up of only
the elements carbon and hydrogen. They may
be aliphatic or aromatic.
Aliphatic hydrocarbons. Aliphatic hydrocarbons
can be divided into three subgroups.
• Alkanes have only C – C σ bonds and no
functional group. Ethane, CH3CH3, is a simple
alkane.
• Alkenes have a C – C double bond as a
functional group. Ethylene, CH2––CH2, is a
simple alkene.
• Alkynes have a C – C triple bond as a functional
group. Acetylene, HC–CH, is a simple alkyne.
 • Aromatic hydrocarbons. This class of hydrocarbons was so named
because many of the earliest known aromatic compounds had strong,
characteristic odors.
• The simplest aromatic hydrocarbon is benzene. The six-membered
ring and three π bonds of benzene comprise a single functional
group. Benzene is a component of the BTX mixture (B for benzene)
added to gasoline to boost octane ratings.

When a benzene ring is bonded to another group, it is called a phenyl group. In phenylcyclohexane, for example,
a phenyl group is bonded to the six-membered cyclohexane ring.
• Alkanes, which have no functional groups,
are notoriously unreactive except under
very drastic conditions.
• For example, polyethylene is a synthetic
plastic and high molecular weight
alkane, consisting of chains of –CH2 –
groups bonded together, hundreds or even
thousands of atoms long.
• Because it is an alkane with no reactive
sites, it is a very stable compound that does
not readily degrade and thus persists for
years in landfills.
2. Compounds Containing C–Z σ Bonds
• Several types of functional groups that contain C – Z σ bonds are listed in
Table. The electronegative heteroatom Z creates a polar bond, making
carbon electron deficient. The lone pairs on Z are available for reaction with
protons and other electrophiles, especially when Z = N or O.

Several simple compounds in this category are widely used. As an example,

chloroethane (CH3CH2Cl, commonly called ethyl chloride) is an alkyl halide used
as a local anesthetic. Chloroethane quickly evaporates when sprayed on a
wound, causing a cooling sensation that numbs the site of an injury.
• Molecules containing these functional groups may be simple or very complex. Diethyl ether, the first
common general anesthetic, is a simple ether because it contains a single O atom, depicted in red,
bonded to two C atoms.
• Hemibrevetoxin B, on the other hand, contains four ether groups, in addition to other functional groups.
3. Compounds Containing a C––O Group
• Many different types of functional
groups possess a C – O double bond
(a carbonyl group), shown in Table.
• The polar C – O bond makes the
carbonyl carbon an electrophile,
while the lone pairs on O allow it to
react as a nucleophile and base.
• The carbonyl group also contains a
π bond that is more easily broken
than a C – O σ bond.
• Atenolol and donepezil are examples of useful drugs
that contain a variety of functional groups. Atenolol is a
β blocker, a group of drugs used to treat hypertension.

• Donepezil, sold under the trade name Aricept, is used

to treat mild to moderate dementia associated with
Alzheimer's disease.
Importance of a Functional Group
• The importance of a functional
group cannot be overstated.
• A functional group determines all
the following properties of a
molecule: