Organic Chemistry

(PHC 211)

By
Dr. Manal Alossaimi
Assistant Professor,
Pharmaceutical Analytical Chemistry
Prince Sattam Bin Abdulaziz University
Introduction of organic
chemistry
Organic chemistry
- is the chemistry of compounds containing carbon.
- Because carbon has four valence electrons, it can form four
covalent bonds.
- Carbon forms single, double, and triple bonds to achieve a
filled octet.

C C C C

- A unique feature of carbon is its ability to bond with other carbons

to form long straight chains or rings of various length.
 Simplest Organic molecule

Carbon has 4 valence electrons

H H
H C H H C H Ne
H H Neon
methane
H C

Stable Octet required

Covalent Bonding – Atoms Share Electrons

 C(6) - 1s2, 2s2, 2px1, 2py1, 2pz0

lowest energy
state

2 1 1 1 1
C(6) - 1s , 2s , 2px , 2py , 2pz
Excited state
4 sp3 Hybridization

+ + +
2s 2py 2px 2pz 4 X sp3
 Methane is Tetrahedral

0
109.5
H
C H
H
H
Sp3 hybridized carbon
4 equivalent C-H bonds (s-bonds)
All purely single bonds are called s-bonds
 H H
120o C C Flat molecule – “Planar”

H H
C(6) - 1s2, 2s , 2px1, 2py1, 2pz0
2

Hybridization
2 1 1 1 1
C(6) - 1s , 2s , 2px , 2py , 2pz

H H 3 sp2
C C p-bond
H H
Three s-bonds
p-bond s-bonds – One C-C, two C-H bonds per carbon atom
 s-orbital s-bond
p-orbitals

Spherical Symmetry
end to end overlap of orbitals leads to s-bond
When a single bond is
present between atoms, that
bond is always s-bond
p-bond Double bond(DB) contains one
side ways overlap s-bond and one p-bond

The p-bond lies perpendicular to the s-bond –

overlapping lobes above and below the plane of s-
bond
Groups or atoms can be rotated about a single bond, but DB is
rigid. No rotation about a DB is possible without breaking the p-
bond. This leads to cis-trans isomerism.
 If each of the two carbons has two different groups attached to it

Geometric isomers have R R R H

different chemical &
physical properties
H H H R

cis- trans-
H3C CH3 H3C H

H H H CH3

cis-(Z)-2-butene trans-(E)-2-butene

Z-E system, we take the group with higher priority (here

higher molecular weight), and compare it with the group
with higher priority on the other carbon
 Chemical Bonding

Chemical bond: Force that holds groups of two or more atoms together.
Or
It is an attraction between atoms that allows the formation of chemical substances that
contain two or more atoms.

Example: H-O-H

Bond Energy: Energy required to break a bond.

Ionic Bond: Attractions between oppositely charged ions. Bond formed between two ions
by the transfer of electrons. Ionic compounds result between atoms of metals and nonmetals
with very different electronegativity
Examples; NaCl, CaCl2, K2O

Na+ Cl-
Covalent Bond: bond formed by the sharing of electrons by nuclei.
Example: H-H, H-F

Polar Covalent Bond: Unequal sharing of electrons by nuclei because of difference of

electronegativity.
Example: H-F, H-Cl
Hydrogen fluoride is an example of a molecule that has bond polarity.

Non-polar Covalent Bond: Equal sharing of electrons by nuclei.

Example: H-H, Cl-Cl

Single Bond: Two atoms sharing one electron pair.

Example: H2

Double Bond: Two atoms sharing two pairs of electrons.

Example: O2

Triple Bond: Two atoms sharing three pairs of electrons.

Example: N2
 Electronegativity

The relative ability of an atom in a molecule to attract shared electrons to itself.

Example: Fluorine has the highest electronegativity.

Similar electronegativities between elements give non-polar covalent bonds

Different electronegativities between elements give polar covalent bonds

If the difference between the electronegativities of two elements is greater, the bond is
ionic.
 Cleavage of Covalent Bonds
Homolytic cleavage: each atom involved in the covalent bond
receives one electron, resulting in formation of free radical

Hetrolytic cleavage: both bonding electrons are retained by

one of the atoms, resulting in formation of ionic species
Heterolysis of Bonds to Carbons:
Carbanions and Carbocations
Reaction can occur to give a carbocation or carbanion
depending on the nature of Z
Heterolysis of Bonds to Carbons:
Carbanions and Carbocations
Carbocations have only 6 valence electrons and a positive charge

Carbanions have 8 valence electrons and a negative charge.

*Electrophiles (“electron-loving” reagents): seek electrons to
obtain a stable valence shell of electrons
Are electron-deficient themselves e.g. carbocations

*Nucleophiles (“nucleus-loving” reagents): seek a proton or

some other positively charged center
Are electron-rich themselves e.g. carbanions
Lewis structure frequently contain atoms that bears a
positive or negative charge.

If the molecule as a whole is neutral , the sum of its

positive charges must equal to the sum of its negative
charges.