Week 1: Introduction to Organic Chemistry

(Part 1)

Objectives:

1. Define Organic Chemistry.

2. Determine the differences between organic and inorganic
compounds.
3. Enumerate the different formulas used in Organic Chemistry and
give examples.
4. Identify the different types of bonds.
Introduction 
In 1685, Nicolas Lemery, a French Chemist, classified substances as
animals, vegetables or minerals on the basis of their origin. This was
probably the first attempt made to distinguish substances derived from
plant or animal sources from those obtained from mineral constituents. The
term organic was later applied to those compounds derived from living
matter and substances originated from nonliving sources were referred to
as inorganic. It is also the belief of scientist then that living organisms
contained some mysterious vital force necessary to the formation of
organic substance. Organic compounds cannot be prepared in the
laboratory using inorganic starting materials.
 In 1814, a Swedish chemist, JJ Berzelius, dealt a vital force
theory a serious blow when he proved that the basic laws of
chemical change applied both to organic and inorganic compounds.

The birth of modern organic chemistry was placed in 1828. It

was the year that Friedrich Wohler, a German professor in
Chemistry, attempted to prepare ammonium cyanate (NH4CNO) by
heating a mixture of two inorganic salts, potassium cyanate (KCNO)
and ammonium chloride (NH4Cl).
But instead of producing ammonium cyanate, he obtained crystals of
well-known organic compound, urea (N2H4CO).

Urea is an organic compound found in the urine of mammals.

Because of this discovery, many other organic compounds were
synthesized from inorganic starting materials in the chemical
laboratories.

By 1850, the vital force theory was essentially dead, and the
relationship between the two branches of chemistry was clearly
recognized.
 Contrasting Properties of Organic and Inorganic Compounds.

Organic Compounds Inorganic Compounds

1. low melting point 1. high melting point
2. low boiling point 2. high boiling point
3. low solubility in water; high 3. high solubility in water; low
solubility in non-polar solubility in non-polar solvents
solvents
4. flammable 4. non-flammable
 Organic Compounds
5. solutions are non-conductor
of electricity
6. chemical reactions are
usually slow
7. Exhibit isomerism
8. Exhibit covalent bonding
9. Exists as solid, liquids, and
gases at room temperature
Inorganic Compounds
5. solutions are good conductor
of electricity
6. chemical reactions are rapid
7. isomers are limited to few
exceptions
8. exhibit ionic bonding
9. exists predominantly as solids
at room temperature
 One constituent common to all organic compounds is the
element carbon. The term organic chemistry, although no longer
descriptive, implies the study of carbon-containing compounds.
There are approximately 500,000 known inorganic compounds,
while there are about 19 million known organic compounds.

What is so unique about carbon that differentiates it from all

other elements in the periodic table is that carbon has the ability to
bond successively to other carbon atoms to form chains and rings of
varying sizes. Carbon can also form equally strong bonds with a
number of different elements. Among these are hydrogen, oxygen,
nitrogen, sulfur, phosphorus and the halogens.
Chemical Bond
 

A chemical bond is a lasting attraction between atoms,

ions or molecules that enables the formation of chemical
compounds. It is related to the arrangement of electrons in
compounds. The bond may result from the electrostatic
force of attraction between oppositely charged ions as in
ionic bonds or through the sharing of electrons as
in covalent bonds. Thus, the nature of chemical bonds is
closely related to electron configurations.
Chemical Bond
A chemical bond is a lasting attraction between atoms, ions or molecules that
enables the formation of chemical compounds. It is related to the arrangement of
electrons in compounds. The bond may result from the electrostatic force of attraction
between oppositely charged ions as in ionic bonds or through the sharing of electrons
as in covalent bonds. Thus, the nature of chemical bonds is closely related to electron
configurations.
Types of Bond (a review from CHM 101))

1. Ionic bond
Ionic bonds are a class of chemical bonds that result from the exchange of one or
more valence electrons from one atom, typically a metal, to another, typically a
nonmetal. This electron exchange results in an electrostatic attraction between the
two atoms called an ionic bond. An atom that loses one or more valence electrons to
become a positively charged ion is known as a cation, while an atom that gains
electrons and becomes negatively charged is known as an anion.
This exchange of valence electrons allows ions to achieve electron
configurations that mimic those of the noble gases, satisfying the octet
rule. The octet rule states that an atom is most stable when there are
eight electrons in its valence shell. Atoms with less than eight electrons
tend to satisfy the duet rule, having two electrons in their valence shell.
By satisfying the duet rule or the octet rule, ions are more stable.
Once the oppositely charged ions form, they are attracted by their
positive and negative charges and form an ionic compound. Ionic bonds
are also formed when there is a large electronegativity difference
between two atoms. This difference causes an unequal sharing of
electrons such that one atom completely loses one or more electrons
and the other atom gains one or more electrons, such as in the creation
of an ionic bond between a metal atom (sodium) and a nonmetal
(chlorine).
 A cation is indicated by a positive superscript charge (+ something) to
the right of the atom. An anion is indicated by a negative superscript
charge (- something) to the right of the atom. For example, if a sodium
atom loses one electron, it will have one more proton than electron, giving
it an overall +1 charge. The chemical symbol for the sodium ion is Na +1 or
just Na+. Similarly, if a chlorine atom gains an extra electron, it becomes
the chloride ion, Cl–. Both ions form because the ion is more stable than
the atom due to the octet rule.
 Example 1: MgF2
Magnesium and fluorine combine to form an ionic compound. What
is the formula for the compound?
Mg forms a 2+ ion since it has two valence electrons and it would like
to get rid of those two electrons to follow the octet rule. Fluorine has
seven valence electrons and as such, usually forms the F– ion because it
gains one electron to satisfy the octet rule. When Mg2+ and F–  combine
to form an ionic compound, their charges must cancel out. Therefore,
one Mg2+ needs two F– ions to balance. The 2+ of the Mg is balanced by
having two -1 charged ions. Therefore, the formula of the
compound is MgF2. The subscript two indicates that there are two
fluorine that are ionically bonded to magnesium
 Example 2: Al2O3

Iron and oxygen combine to form an ionic compound. What is the formula for the
compound?
Al forms a 3+ ion since it has three valence electrons and it would like to get
rid of those three electrons to follow the octet rule. Oxygen has six valence electrons
and as such, usually forms the O–2 ion because it gains two electrons to satisfy the octet
rule. When Al3+ and O–2 combine to form an ionic compound, their charges must cancel
out. Therefore, two Al3+ needs three O2– ions to balance. The 3+ of the Al is balanced by
having three -2 charged ions. Therefore, the formula of the compound is Al2O3. The
subscript three indicates that there are three oxygens that are ionically bonded to
aluminum.
2. Covalent Bonds

Covalent bonds are a class of chemical bonds where valence electrons are shared
between two atoms, typically two nonmetals. The formation of a covalent bond allows
the nonmetals to obey the octet rule and thus become more stable. For example:

A chlorine atom has seven valence electrons. If it shares one electron with a carbon
atom (which has four valence electrons), the chlorine will have a full octet (its seven
electrons plus the one it is sharing with carbon).

Carbon will then have five valence electrons (its four and the one its sharing with
chlorine). Covalently sharing two electrons is also known as a “single bond.” Carbon
will have to form four single bonds with four different chlorine atoms to fill its octet.
The result is CCl4 or carbon tetrachloride.
 And in every pair shared electron, there is the formation of single covalent bond:
Covalent bonds can be single, double, and triple bonds.

Single bonds occur when two electrons are shared and are composed of one sigma
bond between the two atoms.

Double bonds occur when four electrons are shared between the two atoms and
consist of one sigma bond and one pi bond.
 Triple bonds occur when six electrons are shared between the two atoms and consist of one
sigma bond and two pi bonds.

References: T.W. Graham Solomons and Craig B. Fryhle. (2008) Organic Chem.
H. Stephen Stoker. (2010) Exploring General, Organi, and Biological Chemistry.
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