INTRODUCTION

Chem 211E: Organic Chemistry

Engr. KBDimalanta
Organic chemistry used to refer to the chemistry of compounds that come from
living organisms.
Late 1700s:
▪ ‘Organic’ substances came from plants and animals while ‘inorganic’
substances were derived from minerals.
▪ Little knowledge in chemistry; it is assumed that organic and inorganic
substances behaved differently.
▪ Organic compounds were observed to generally be low MP solids which
were more difficult to isolate/purify/work with.
Mid-1800s:
▪ Organic substances are not fundamentally different from inorganic
substances → they follow the same principles and laws.
▪ ALL ORGANIC SUBSTANCES CONTAIN CARBON.
 - More than 99% of the >30M known chemical compounds contain
carbon, from the simplest ones to the most complex.

• Carbon is an element that belongs to group 4A in the periodic

table.
✓ Stable C atoms are tetravalent.
✓ C can share 4 electrons → forms 4 strong covalent bonds.
✓ C atoms can bond to each other → can form chains and rings.

• Remember! It is already scientifically proven and currently

applied that not all carbon compounds are derived from living
organisms; some are designed and synthesized.
I. Structure
& Bonding
Chem 211E: Organic Chemistry
Engr. KBDimalanta
REVIEW: The
Dalton’s atomic theory is based on the following hypotheses:
Atomic Structure

1. Lewis Structures ▪ Elements are composed of indivisible particles called atoms.

These atoms can neither be created nor destroyed.
2. Resonance
▪ All atoms of a given element are identical, having the same size,
3. Molecular Shapes mass, and chemical properties. Atoms of one element are
and Saturation different from the atoms of all other elements.
4. Hybridization ▪ Compounds are composed of atoms of more than one element.
In any compound, the ratio of the numbers of atoms of any two of
5. Bond Length &
Bond Strength
the elements present is either an integer or a simple fraction.
▪ A chemical reaction involves only the separation, combination, or
6. Electronegativity
and Polarity
rearrangement of atoms; it does not result in their creation or
destruction.
REVIEW: The
The laws governing the formation of
Atomic Structure compounds:
1. Law of definite proportions → a compound
1. Lewis Structures
will always contain its constituent elements
2. Resonance in the same proportion by mass.
2. Law of multiple proportions → if two
3. Molecular Shapes
and Saturation
elements can combine to form more than
one compound, the masses of one
4. Hybridization element that combine with a fixed mass of
5. Bond Length &
the other element are in ratios of small
Bond Strength whole numbers.
3. Law of conservation of mass → in a
6. Electronegativity
and Polarity
chemical reaction, mass is neither created
nor destroyed. It remains constant
REVIEW: The
In the middle of the atom sits the nucleus which is dense and
Atomic Structure positively charged. It is surrounded by a much larger negatively
charged electron cloud.
1. Lewis Structures

2. Resonance

3. Molecular Shapes
and Saturation

4. Hybridization A specific atom is defined by its atomic number (or its number of
5. Bond Length &
protons). SAME ATOMIC NUMBER = SAME ELEMENT.
Bond Strength
𝐴
6. Electronegativity
and Polarity
𝑋 : element
𝐴 : mass number
𝑍 : atomic number
𝑍 𝑋
REVIEW: The
Atomic Structure

1. Lewis Structures

2. Resonance

3. Molecular Shapes
and Saturation

4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity
REVIEW: The
▪ Electrons move very quickly and it is near impossible to track
Atomic Structure their exact movement.
▪ The behavior of a specific electron in an atom can be described
1. Lewis Structures
by a mathematical expression called a wave equation.
2. Resonance ➢ The solution to a wave equation is called a wave function,
or orbital (𝜓).
3. Molecular Shapes
and Saturation
➢ The square of the wave function (𝜓2) plotted in 3D space
describes the volume around a nucleus that an electron
4. Hybridization usually occupies
5. Bond Length &
Bond Strength
FOUR TYPES OF
6. Electronegativity
and Polarity
ORBITALS: s, p, d, f.
REVIEW: The We can think of an electron’s specific orbital as where it likes
Atomic Structure to spend most (~90-95%) of its time.
1. Lewis Structures
s orbital
2. Resonance • spherical electron density, with the nucleus at the center.
• lower in energy compared to other orbitals of the same shell,
3. Molecular Shapes
and Saturation because electrons are kept close to the positively charged
nucleus.
4. Hybridization
p orbitals
5. Bond Length & • dumbbell-shaped; there are three (3) different p orbitals in a
Bond Strength
shell, oriented in space along mutually perpendicular directions:
6. Electronegativity 𝑝𝑥, 𝑝𝑦, and 𝑝𝑧.
and Polarity • higher in energy than an s orbital (in the same shell) because its
electron density is farther away from the nucleus.
REVIEW: The
p orbitals (cont.)
Atomic Structure
▪ each p orbital has two lobes, separated by a node (a region with
1. Lewis Structures
no electron density), and each has a different algebraic sign, +
2. Resonance and –, represented by the different colors shown below:
3. Molecular Shapes
and Saturation

4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity
REVIEW: The
d orbitals
Atomic Structure

1. Lewis Structures

2. Resonance

3. Molecular Shapes
and Saturation

4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity
REVIEW: The
s, p, d, and f orbitals
Atomic Structure

1. Lewis Structures

2. Resonance

3. Molecular Shapes
and Saturation

4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity
 • The orbitals are organized into different layers, or electron
REVIEW: The shells. Different shells contain different numbers and kinds of
Atomic Structure
orbitals. Each orbital within a shell can only be occupied by two
1. Lewis Structures (2) electrons.
• Electrons in the inner shell of orbitals are called core electrons
2. Resonance
while the outermost electrons are called valence electrons.
3. Molecular Shapes
and Saturation

4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity

Distribution of electrons in each orbital contained in an electron shell.

 In the mid-19th century, several theories were proposed regarding
REVIEW: The
Atomic Structure carbon such as:
▪ Carbon’s tetravalence.
1. Lewis Structures ▪ Carbon’s ability to bond with other carbon atoms to form chains
2. Resonance and rings.
▪ Carbon’s ability to form multiple bonds.
3. Molecular Shapes
▪ The 3D geometry of the molecules formed by carbon’s bonds.
and Saturation

4. Hybridization BUT WHY DO ATOMS BOND TOGETHER?

→ Atoms undergo bonding because the end product is more
5. Bond Length &
Bond Strength stable, or lower in energy, than the separate atoms.

6. Electronegativity
and Polarity
REVIEW: The Based on observation, the presence of eight (8) electron’s in an
Atomic Structure atom’s valence shell, imparts a special kind of stability to the noble
1. Lewis Structures gases in group 8A.
No. of electrons in each
2. Resonance shell:

3. Molecular Shapes Ne: 2 + 8

and Saturation
Ar: 2 + 8 + 8
4. Hybridization
Kr: 2 + 8 + 18 + 8
5. Bond Length &
Bond Strength Etc.
6. Electronegativity
and Polarity
REVIEW: The ▪ The main group elements are governed by their tendency to try
Atomic Structure and achieve the electron configuration of the nearest noble gas
1. Lewis Structures (i.e. they want to achieve the 8-valence electron configuration by
either gaining or losing electrons).
2. Resonance
▪ However, the elements in the middle part of the periodic table
3. Molecular Shapes form bonds by sharing electrons rather than by gaining/losing
and Saturation electrons. The bonds formed here are called covalent bonds.
4. Hybridization ▪ The number of covalent bonds to be formed depends on how
many additional valence electrons an atom needs to reach the
5. Bond Length &
Bond Strength noble gas/8-valence electron configuration.

6. Electronegativity
and Polarity 𝒑𝒓𝒆𝒅𝒊𝒄𝒕𝒆𝒅 𝒏𝒖𝒎𝒃𝒆𝒓 𝒐𝒇 𝒃𝒐𝒏𝒅𝒔 = 𝟖 − 𝒏𝒖𝒎𝒃𝒆𝒓 𝒐𝒇 𝒗𝒂𝒍𝒆𝒏𝒄𝒆 𝒆𝒍𝒆𝒄𝒕𝒓𝒐𝒏𝒔
REVIEW: The The bonding and nonbonding electrons of some elements.
Atomic Structure

1. Lewis Structures

2. Resonance

3. Molecular Shapes
and Saturation Source: McMurry (2018)

4. Hybridization

5. Bond Length &

The nonbonding electrons are also called lone-pair electrons.
Bond Strength

6. Electronegativity
and Polarity
REVIEW: The Bonding vs. non-bonding electrons:
Atomic Structure

1. Lewis Structures

2. Resonance

3. Molecular Shapes
and Saturation

4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity
Source: Smith (2010)
REVIEW: The LEWIS vs. KEKULÉ STRUCTURES
Atomic Structure

1. Lewis Structures

2. Resonance

3. Molecular Shapes
and Saturation

4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity
Source: McMurry (2018)
 Below are steps in how to draw a Lewis structure:
REVIEW: The
Atomic Structure 1. Arrange atoms next to each other.
2. Count the electrons in each element.
1. Lewis Structures
3. Arrange the electrons around the atoms.
2. Resonance 4. Assign formal charges to all atoms.
3. Molecular Shapes
and Saturation EXAMPLES: 1) Draw a Lewis structure for methanol (𝐶𝐻4 𝑂)

4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity
 2) Draw a Lewis structure for ethylene, a compound with
REVIEW: The
Atomic Structure molecular formula 𝐶2 𝐻4 . Assume the atoms are arranged
as shown
1. Lewis Structures

2. Resonance

3. Molecular Shapes
and Saturation

4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity
 3) Draw a Lewis structure for acetylene, a compound with molecular
REVIEW: The
Atomic Structure
formula 𝐶2 𝐻2 . Assume the atoms are arranged as shown: H C C H

1. Lewis Structures

2. Resonance

3. Molecular Shapes
and Saturation

4. Hybridization

5. Bond Length &

Bond Strength Step [4] Move lone pair
6. Electronegativity
and Polarity
REVIEW: The
To check the validity of the Lewis structure drawn, the answer in
Atomic Structure the following three questions must be YES:
✓ Have all the valence electrons been used?
1. Lewis Structures
✓ Is each 𝐻 surrounded by two electrons?
2. Resonance
✓ Is each second-row element surrounded by no more than
3. Molecular Shapes eight electrons?
and Saturation

4. Hybridization ▪ One lone pair is transformed into one new bond for each two
electrons needed to complete an octet.
5. Bond Length &
Bond Strength
▪ A lone pair forms multiple bonds if the carbon atom was not
6. Electronegativity able to satisfy the octet rule after placing all electrons in bonds
and Polarity
and lone pairs.
REVIEW: The
▪ A formal charge is the charge assigned to individual atoms in a
Atomic Structure Lewis structure.
1. Lewis Structures

2. Resonance

3. Molecular Shapes
and Saturation ▪ The sum of the formal charges on the individual atoms is
equivalent to the net charge on the molecule or ion.
4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity
REVIEW: The
1. HYDROGEN
Atomic Structure ▪ Hydrogen can only accommodate 2 elements in bonding
1. Lewis Structures

2. Resonance

3. Molecular Shapes
and Saturation
2. GROUP 2A AND 3A ELEMENTS
▪ Elements in group 2A and 3A do not have enough valence
4. Hybridization
electrons to form an octet in a neutral molecule.
5. Bond Length & ▪
Bond Strength

6. Electronegativity
and Polarity
REVIEW: The
2. GROUP 2A AND 3A ELEMENTS
Atomic Structure ▪
1. Lewis Structures

2. Resonance

3. Molecular Shapes
and Saturation

4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity
REVIEW: The
3. ELEMENTS IN ROW 3 (Periodic Table)
Atomic Structure ▪ Elements in the third row can have more than eight valence
electrons due to empty d orbitals which can accommodate
1. Lewis Structures
more electrons.
2. Resonance

3. Molecular Shapes
and Saturation

4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity
REVIEW: The
3. ELEMENTS IN ROW 3 (Periodic Table)
Atomic Structure

1. Lewis Structures

2. Resonance

3. Molecular Shapes
and Saturation

4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity
REVIEW: The 1. McMurry, J. (2008). Organic Chemistry, 7th Edition. Thomson
Atomic Structure
Brooks/Cole, USA.
1. Lewis Structures
2. Smith, J.G. (2010). Organic Chemistry, 3rd Edition. McGraw
2. Resonance Hill, USA.
3. Molecular Shapes
and Saturation

4. Hybridization

5. Bond Length &

Bond Strength

6. Electronegativity
and Polarity