ORGANIC CHEMISTRY

MODULE 1
TOPIC: INTRODUCTION TO ORGANIC CHEMISTRY
LEARNING OUTCOMES:
1. To recognize the importance of organic compounds
2. To become familiar with the method of indicating covalent bonding in organic compounds
3. To be able to draw and understand structural formulas
PRE-TEST
I. Identify the number of covalent bonds formed in the following compounds:

1. CH 3 Cl

2. CaCl 2❑

3Cl 2

4. NH 3

5. CO 2

CONTENT
Introduction
Organic Chemistry touches our lives in so many ways. It is the chemistry associated with all living matter in
both plants and animals. Organic chemicals are all around us. The proteins that make up our hair, skin and
muscles are organic chemicals. The nucleic acids that control our genetic heritage are organic chemicals. The
foods we eat, fats, carbohydrates, enzymes are organic chemicals. Wool, silk, cotton, linen and such synthetic
fibers as nylon, rayon and dacron contain organic compounds. So do perfumes, dyes, flavors, soaps,
detergents, plastics, gasolines, and oils.
Organic Chemistry has also been defined as the chemistry of carbon compounds. Since carbon is almost
always associated with hydrogen, organic chemistry may also be defined as the chemistry of hydrocarbons.
Hydrocarbons are compounds containing hydrogen and oxygen.
Distribution of Electrons Among the Shells and Subshells of an Atom:
Any discussion of organic compounds reverts ultimately to a consideration of valency theory in its widest sense
as including the nature of bond, its strength and reactivity. A deeper understanding of the nature of the bond is
achieved when the electronic structures of the atoms and the electronic forces between the electrons and the
nuclei are correlated. This requires a review of the distribution of electrons among the shells and subshells of
an atom using the electron configuration diagram.
Electrons are found outside the nucleus of an atom. The regions of space where electrons move are called
orbitals. The main energy levels are designated by capital letters K, L, M, N shells or 1st, 2nd, 3rd, 4th main
energy levels. Subshells are designated by letters s (spin), p (principal), d (diffuse) and f (fundamental). An
orbital can hold a maximum of 2 electrons. An s sublevel has only one orbital, and can hold only 2 electrons; a
p sublevel has 3 orbitals, and can therefore hold a maximum of 6 electrons; a d sublevel has 5 orbitals, 10
electrons and an f sublevel has 7 orbitals, and can accommodate a maximum of 14 electrons.
 The orbitals in each shell are grouped as follows:
K L M N
2 2 2 2
1s 2s 3s 4s
6 6 6
2p 3p 4p
10 10
3d 4d
14
4f
In considering the way in which the electrons in an atom distribute themselves among the various orbitals, some
principles are used as guides:
1. Electrons tend to go into orbitals of lowest energy level. In other words, electrons tend to occupy orbitals as
close to the nucleus as possible because of the attraction between the nuclear charge and the electrons. There
is a greater tendency for an electron to occupy a 1s orbital than a 2s and a 2s more than a 2p. thus the single
electron in a hydrogen atom will locate itself in a 1s orbital.
2. At any one energy level, electrons tend to occupy separate orbitals. This is in accordance with Hund’s Rule,
which states that electrons tend to avoid being in the same orbital.
The arrangement of electrons in the free atom of any element can be worked out from the spectra of the
element and from its chemical properties in relation to its positon in the periodic table. This arrangement of
electrons of the elements in the free state is known as electronic configuration.
Electronic Configuration of Some Elements Found in Organic Compounds
Element Symbol At. No. Electronic configuration No. of valence e
1
Hydrogen H 1 1s 1
2 2
Berrylium Be 4 1s 2s 2
2 2 1
Boron B 5 1s 2s 2 p 3
2 2 2
Carbon C 6 1s 2s 2 p 4
2 2 3
Nitrogen N 7 1s 2s 2 p 5
2 2 4
Oxygen O 8 1s 2s 2 p 6
2 2 5
Fluorine F 9 1s 2s 2 p 7

The number of valence electrons of each element listed above is determined by considering the electrons in the
last s and p sublevels.
Bonding:
Organic compounds are held together by covalent bonds. Recall that covalent bonds are formed by sharing of
electrons. In organic chemistry, the term bond is used to designate a shared pair of electrons. A simple way of
indicating the covalent bonds in molecules is to use the Lewis structure or the electron dot structure. Simpler
still is the use of Kekule’s structure or line-bond structure in which the covalent bond formed is indicated as a
line drawn between atoms. From the electronic configuration given above, it is shown that H has one unpaired
electron, while oxygen has two unpaired electrons. For these elements, the number of unpaired electrons
indicate the covalency number. Hydrogen with one unpaired electron has a covalency number of 1. Oxygen, on
the other hand, has a covalency number 2.
H----H one covalent bond is formed

H ---- O---- H two covalent bonds are formed

Nitrogen on the other hand, forms three covalent bonds
H ---- N ----H
H
The carbon to carbon bond in ethane, C2H6 is covalent. The 2 bonding electrons are shared equally by the 2
equivalent carbon atoms.
Electronegativity
Bond polarity is due to the difference in electronegativity. Electronegativity is the intense ability of an atom to
attract the shared electrons in a covalent bond. Metals on the left side of the Periodic Table attract electrons
weakly and have lower electronegativities. While O, N, and halogens attract electrons strongly and have high
electronegativities.
Electronegativity increases from left to right in the Periodic Table and decreases from top to bottom. As a
guide, a bond between atoms with similar electronegativities is covalent; a bond between atoms whose
electronegativities differ by less than 2 units is polar covalent, and a bond between 2 atoms whose
electronegativities differ by 2 or more is largely ionic.
Electronegativity of some common elements:
H = 2.1 Li = 1
Na = 0.9 K = 0.8
Rb = 0.8 Cs = 0.7
B =2 C = 2.5
Al = 1.5 Ga = 1.8
N =3 O = 3.5
A C-H bond is relatively non-polar because carbon and hydrogen have similar electronegativities, 2.1 and 2.5,
respectively.
A bond between carbon and oxygen or nitrogen is polar covalent. ( the difference between the
electronegativities of C =2.5 and O =3.5 is one (1),and is less than 2 units)
Properties of Carbon
As mentioned earlier, Organic Chemistry is the chemistry of carbon compounds. But why carbon? Of the 121
elements identified, why is there a specific chemistry for carbon compounds? What properties does carbon
have that makes it unique/different from other elements?
Enumerated below are the unique properties of carbon:
1. Carbon has four strong bonds.
 If you may recall, from the distribution of electrons among the shells and subshells of carbon atom, its
first main energy level sublevel s is completely filled as well as the second main energy level sublevel s. its
second main energy level, sublevel p is incompletely filled, having only two electrons. Considering the last s
and p sublevels, carbon shows that it has four valence electrons. This means that Carbon can form a maximum
of four covalent bonds.
Electronic configuration of C with 6 electrons:
2 2 2
1s 2s 2 p
2. Carbon has four (4) affinity units, meaning it can bond with four (4) other elements to form
compounds. It needs to bond with 4 atoms to attain a noble gas configuration with 8 electrons in the outermost
shell.
With 4 valence electrons, the electron dot symbol of carbon is
C
It has four bonds attached to it. If these bonds are symmetrically arranged, the
planar representation of the structure is:

- C -

3. Carbon has the unique ability to bond together forming long chains and rings. Carbon atoms can
join together to form continuous or branched chain of carbon atoms. Compounds of this type are called
aliphatic compounds. Carbon compounds can also bond together in the shape of rings to form cyclic
compounds also called aromatic compounds. Another type of organic compounds are the heterocyclic
compounds, which also have a ring structure. However, this ring structure contains some element other than
carbon in the ring.

C-C-C-C-C or

Aliphatic aromatic heterocyclic

Structural Formulas
Organic compounds are often written using a structural formula rather than a molecular formula. What is the
difference between a structural formula and a molecular formula? And why use the former and not the latter?
A structural formula shows the exact way in which the atoms are connected to each other, but a molecular
formula does not. You cannot tell the structure of a molecule from its molecular formula.
If the carbons and hydrogen in C2 H6 are arranged in such a manner that each atom of carbon atom has four
bonds attached to it, and each hydrogen atom has one bond, then the structural formula for the compound is:
In the diagram shown above, the lines represent bonds or shared electrons. It is simpler to write a structural
formula using the bond notation.
Example:

Draw the structural formula for C 5 H 12

Solution:
There are three possibilities for the arrangement of five carbon atoms.
1. Five carbon atoms in a row:

2. Four carbons in a row with the fifth carbon attached to

one of the middle carbon:

3. Three carbons in a row, with the two other carbons attached to the middle carbon.

The three compounds shown above have different structures and different properties and are actually different
compounds. They are called isomers. They have the same molecular formulas but different connectivity of the
atoms or groups. This difference in the structure of compounds having the same molecular formula illustrates
the importance of using structural formula rather than molecular formula for organic compounds.

ASSESSMENT
I. Identify the number of covalent bonds formed in the following compounds:

1. CH 3 Cl

2. CaCl 2❑

3Cl 2

4. NH 3
5. CO 2

II. Draw the electronic configuration of the following elements, given their atomic numbers:
1. Mg - 12 4. K - 19
2. S - 16 5. Ne - 10
3. Ca - 20

III. Propose structures for five isomers with formula C 8 H 18

IV. Phosphorus is in group VA of the periodic table. How many bonds should be attached to the phosphorus
atom?
REFERENCES
McMurry, John E., Organic Chemistry, 2015
Sylianco, Clara Lim, Principles of Organic Chemistry, 2019