Organic chemistry

DNA

KI 1, MA
Alloh SWT menciptakan
Manusia dan kebutuhan
kepada manusia tidak
pernah Main-main
Dengan perhitungan yang
Amat Cerdas dan Luar Biasa

 The basic structure of

testosterone (male hormone) and
estradiol (female hormone) is
identical.
Both are steroids with four fused carbon
rings, but they differ in the functional
groups attached to the rings.

These then interact with different

targets in the body.

Fig.4.8
Copyright2002PearsonEducation,Inc.,publishingasBenjaminCummings

mirror
plane
OH
H
HO 2C

OH
CH3

(S)(+) lactic acid

from muscle tissue
o
[] = +13.5

CH3

H
CO 2H

(R)(-) lactic acid

from milk
o
[] = -13.5

observed rotation
x
100
=
enantiomeric
excess
(e.e.)
rotation of pure enantiomer
o

observed rotation = +109

109.0
e.e. = 123.0 x 100
H

H
(S)-(-) Limonene
o

[=
from lemons

= 88.6% e.e.

88.6% (+)
(R)(+) Limonene
11.4% racemic
o
[] = +123.0
actually 94.3% (+)
from oranges

Some organic chemicals

Medicines

DNA

Active Pharmaceutical Ingredients

Excipients
Fuels

Materials

Essential oils

Pigments

Organic chemicals make up

Foods and foodstuf

Flavours and fragrances
Medicines
Materials, polymers, plastics
Plant, animal and microbial matter;
natural products
A vast range of manufactured goods
[pharmaceuticals, foods, dyestufs, adhesives, coatings,
packaging, lubricants, cosmetics, films & fibres, etc. etc.]

Salt versus Molecules

A metal cation and nonmetal anion are
joined together by an ionic bond called SALT

A group of atoms joined together

by a covalent bond is called a
MOLECULE
A Compound is a group of two or
more elements bonded together
(Ionic or Covalent).

Molecular Orbitals
Just

as atomic orbitals belong to a

particular atom, a molecular orbital
belongs to molecules as a whole

Each orbital is filled with 2 electrons

A Bonding Orbital is an orbital that can
be occupied by two electrons of a
covalent bond
(its the space in
between
the
two atoms)
There are
2 types
of bonding
orbitals: sigma and pi

Covalent Bonds
When two nonmetals bond, they
often share electrons since they have
similar attractions for them. This
sharing of valence electrons is called
the covalent bond.
These atoms will share sufficient numbers of
electrons in order to achieve a noble gas electron
configuration (that is, eight valence electrons).

Copyright Houghton
Mifflin Company.All rights

Presentation of Lecture Outlines,

914

Sigma Bond ()
A Sigma Bond is when 2 atomic
orbitals combine to form a molecular
orbital that is symmetrical around
the
axis
S orbitals overlapping

P orbitals overlapping end-to-end

Pi Bond ()
Pi bonding electrons are likely to be found in
a sausage-shape above and below the axis
Pi

bonds are weaker than sigma bonds

because they overlap less

P orbitals overlapping
side-by-side

Secara
energetik
kimia terjadi sebagai efek energi kedua

Ikatan
atom yang berdekatan lebih rendah (sekitar 100 kJ
per mol atau lebih) dari pada saat masing-masing
saling terpisah

Covalent Bonds
The tendency of atoms in a
molecule to have eight electrons in
their outer shell (two for hydrogen)
is called the octet rule.

. +.H

Copyright Houghton
Mifflin Company.All rights

H H

Presentation of Lecture Outlines,

918

Covalent Bonding
In these bonds atoms
share electrons.
There are several
electrostatic interactions
in these bonds:
Attractions between
electrons and nuclei
Repulsions between
electrons
Repulsions between nuclei

Polar Covalent Bonds

When two atoms share
electrons unequally, a bond
dipole results.
The dipole moment, ,
produced by two equal but
opposite charges separated
by a distance, r, is
calculated:
= Qr
It is measured in debyes (D).

Polar Covalent Bonds

The greater the
diference in
electronegativity
, the more polar
is the bond.

Lewis Structures

Lewis structures are representations of

molecules showing all electrons,
bonding and nonbonding.

Resonance
This is the
Lewis structure
we would draw
for ozone, O3.

Resonance
But this is at odds
with the true,
observed structure
of ozone, in which
both OO bonds
are the same length.
both outer
oxygens have a
charge of 1/2.

Resonance
One Lewis
structure cannot
accurately depict
a molecule such
as ozone.
We use multiple
structures,
resonance
structures, to
describe the
molecule.

Resonance
Just as green is a
synthesis of blue
and yellow

ozone is a
synthesis of these
two resonance
structures.

Resonance
In truth, the electrons that form the second CO
bond in the double bonds below do not always
sit between that C and that O, but rather can
move among the two oxygens and the carbon.
They are not localized, but rather are
delocalized.

Resonance
The organic compound
benzene, C6H6, has two
resonance structures.
It is commonly
depicted as a hexagon
with a circle inside to
signify the delocalized
electrons in the ring.

The Molecular Orbital Model

The localized electron model does an excellent
job of predicting and justifying molecular
shapes. But it does not deal with molecules
with unpaired electrons. It also neglects bond
energies.
The molecular orbital (MO) model gives a
view of electrons in a molecule which allows
us to get a clearer understanding of resonance.

Molecular Orbital Theory

Regards a molecule as a collection of nuclei
and electrons, where the electrons are assumed
to occupy orbitals much as they do in atoms,
but having the orbitals extend over the entire
molecule.
The electrons are assumed to be delocalized
rather than always located between a given
pair of atoms.

Electron Probability in MO
The electron probability of both
molecular orbitals is centered along the
line passing through the two nuclei.
Sigma () molecular orbitals (MOs)

In the molecule only the molecular

orbitals are available for occupation by
electrons.

Key Ideas of the MO Model

1. All valence electrons in a molecule exist in a set of
molecular orbitals of a given energy.
2. Valence orbitals of each atom are not acting
independently, but rather interact as a whole to form
a set of molecular orbitals.
3. Each pair of atomic orbitals interacts to form a set
of bonding and antibonding molecular orbitals.
4. Energy for bonding molecular orbitals is lower than
their atomic orbitals.
5. Antibonding molecular orbitals have higher energy
that their atomic orbitals.

Combination of Hydrogen 1s Atomic

Orbitals to form MOs

Figure 9.26: (a) MO Energy-Level

Diagram for H2 Molecule, (b) Shapes of MOs

Molecular Orbital Energies

MO1 is lower in energy than the s orbitals
of free atoms, while MO2 is higher in
energy than the s orbitals.
Bonding molecular orbital lower in
energy
Antibonding molecular orbital higher in
energy

MO Energy-Level Diagram for the H2

Molecule

Electron Configurations in MO
Molecular electron configurations can be
written similar to atomic electron
configurations.
Each molecular orbital can hold 2 electrons
with opposite spins.
The number of orbitals are conserved.

Bond Order
Larger bond order means greater bond
strength.
# of bonding e # of antibonding e
Bond order =
2

Bond Order in MO Model

# bonding electrons - # antibonding
BO =
electrons
2

1. Bond order (BO) is a measure of net bonding

interactions.
2. BO must be greater than 0 for a stable molecule to
form.
3. The higher the BO, the stronger the bond.

Example: H2
2 0
Bond order =
=1
2

MO energy-level diagram for first period

elements

To fill molecular orbitals

for atoms containing 1s
valence electrons
(hydrogen and helium):
1. Determine the number of
electrons in the molecule.
2. Fill the energy level
diagram from lowest to
highest energy.
3. Fill each orbital with a
pair of electrons and with
opposite spins.

*1s

E
1s

MO Energy-Level Diagram for He2 Molecule

Bond order for He2 Molecule (2-2)/2 = 0

Bond Order in He2+

2 1 1
Bond order =
=
2
2

Exercises on Molecular Orbitals

Use MO theory to describe the bonding and stability of

a. H22-

b. H2+

H22- has 4
electrons.

H2+ has 1
electron.
*1

*1

1s

1s

BO

2 b.e. - 2
= a.e. 2

=
0

H2 ion will not be

formed.
2-

BO

1 b.e. - 0
= a.e. 2

H2+ may be formed, but it would not

be much more stable than two
separate hydrogens.