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Unit 1 - Lesson 1 - Intro and Structure and Bonding A

Mechanical Engineering Notes

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16 views47 pages

Unit 1 - Lesson 1 - Intro and Structure and Bonding A

Mechanical Engineering Notes

Uploaded by

Cenzhed Camarines
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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CHEM 214

ORGANIC CHEMISTRY
UNIT 1:
Review of the Basic
Structure of Carbon and
Chemical Bonding
CHAPTER 01 STRUCTURE AND BONDING, MC MURRY
1

History of Organic Chemistry


Development of Organic Chemistry as a

Science
In the past …
obtained from
living organisms
obtained from
non-living sources
organisms was
necessary to make an
A “vital force from living organic compound
THE REJECTION OF VITALISM AS A SCIENTIFIC
THEORY
Organic Chemistry Redefined

ORGANIC CHEMISTRY is the study of


carbon compounds obtained from natural
sources or synthesized in the
laboratories.
Scientific Revolution
Scientific revolution leads to:
• Safer and more effective medicines
• Cures for genetic diseases
• Increased life span
• Improved quality of life

Scientific advances in medicine and biology require an


understanding of organic chemistry
q
Synthetic

Dichlorodiphenyltrichloroethane
(DDT) Bisphenol A (BPA)
LEARNING OBJECTIVES
1. differentiated organic from inorganic compounds 2. correctly
illustrated and constructed the electronic structure of carbon
and explained its relation to its chemical properties.
3. described and differentiated the types of atomic and
molecular orbitals.
4. explained the process of hybridization and its relation to the
versatility of carbon and its compound formation.
5. discussed the mechanisms of bond breaking and forming
and the energy requirements.
6. explained in detail the concepts of acids and bases and their
reactions.
UNIT 1: REVIEW OF THE BASIC
STRUCTURE OF CARBON AND
CHEMICAL BONDING
A. STRUCTURE AND BONDING
Common Elements in Carbon Compounds
WHY IS CARBON SPECIAL?
Ability to form four
strong covalent bonds
• Electronic configuration of carbon
(ground state) : 1s22s22p2

Carbon (ground state)


16

Ability to form four


strong covalent bonds
• Each carbon atom has four unpaired
electrons when excited

• Tend to form four strong covalent bonds

Carbon (excited state)

17
Ability to Catenate
• Carbon atoms link
together to form
chains of varying
length,
branched chains and
rings of different
sizes
• Catenation:
🡺 Ability of atoms in
forming stable
bonds with itself,
hence joining up into
chains or rings

Ability to Form Multiple Bonds


sp34σ bonds
sp21π bond, 3σ bonds
sp
2π bonds, 2σ bonds

Carbon (excited state)


19

1.2 Atomic Structure: Orbitals


Quantum Mechanical Model
• Behavior of a specific electron in an atom described
by mathematical expression called a wave equation •
Wave equation is similar to mathematical expression used
to describe motion of waves in fluids
• Solution of wave equation is called a wave function

• Wave function is an orbital


• Orbital denoted by Greek letter psi, ψ
• Plot of ψ 2 describes volume of space around
nucleus that the electron is most likely to occupy •
Electron cloud has no sharp boundary
You might therefore think of an orbital as looking like a
photograph of the electron taken at a slow shutter speed.
Atomic Structure: Orbitals
Four different kinds of orbitals for electrons
• Denoted s, p, d, and f
• s and p orbitals most important in organic and biological
chemistry
• s orbitals

• spherical, nucleus at center


• p orbitals

• dumbbell-shaped, nucleus at middle


• d orbitals

• four cloverleaf-shaped and one dumbbell-doughnut


The Distribution of Electrons in an
Atom ENERGY
• The first shell is closest to the nucleus.
• The closer the atomic orbital is to the nucleus,
the lower its energy.
• Within the same shell, s < p.
-Aufbau principle: An electron goes into the atomic orbital with the lowest
energy.
-Pauli exclusion principle: No more than two electrons can be
in an atomic orbital.
-Hund’s rule: An electron goes into an empty degenerate
orbital rather than pairing up.

CHEMICAL BONDING THEORY


Development of Chemical Bonding Theory
• Atoms form bonds because the resulting compound
is more stable than the separate atoms
• Valence shell: Atom’s outermost shell
• Impart special stability to the noble gas elements •
Ionic bonds - Ions held together by a electrostatic
attraction
• Formed as a result of electron transfers
Development of Chemical Bonding Theory

Ionic compounds
• Some elements achieve an octet configuration by gaining or
losing electrons
• Ions form when an electron is gained or lost from a neutral
atom
• Ions are charged because they have different numbers of
protons and electrons
• Ions are held together by an electrostatic attraction, like in
Na+ Cl-, forming an ionic bond
An ionic bond is formed between metals
and non-metals
Development of Chemical Bonding Theory

Covalent compounds
• Covalent Bond
• Bond formed by sharing electrons between atoms
• Molecule
• Neutral collection of atoms held together by covalent bonds •
Carbon achieves an octet configuration by sharing electrons

Covalent Bonds are Formed by


Sharing Electrons Between
Non-Metals
Nonpolar covalent bond = bonded atoms are the same

No difference in electronegativity between atoms

Polar covalent bond = bonded atoms differ in electronegativity

HOW THE STRUCTURE OF A


COMPOUND IS
REPRESENTED
Development of Chemical
Bonding Theory
• Molecule: Neutral collection of atoms held
together by covalent bonds
• Electron-dot structures: Represents
valence shell electrons of an atom as dots
• Called Lewis structures
• Line-bond structures: Indicates
two-electron covalent bond as a line drawn
between atoms • Called Kekulé structures
Development of Chemical Bonding
Theory

Lewis structures (electron-dot structures)


• Dot representations of covalent bonds in molecules
• Valence shell electrons of an atom are represented as dots

Kekulé structures (line-bond structures)


• Two-electron covalent bond is represented by a line
Development of Chemical Bonding Theory

• Number of covalent bonds an atom forms depends


on the number of additional valence electrons it
needs to reach a stable octet
• Carbon has four valence electrons (2s2 2p2), forming
four bonds
• Nitrogen has five valence electrons (2s2 2p3),
forming three bonds

Non-Bonding Electrons
• Lone pair - Valence electrons not used in
bonding • Example
• Nitrogen atom in ammonia (NH3)
•Shares six valence electrons in three covalent bonds •

Two valence electrons are nonbonding lone pair

Lewis Structures
Lewis structures are representations of
molecules showing all electrons, bonding and
nonbonding.
Writing Lewis Structures
all atoms in the
polyatomic ion or
molecule.
PCl3 • If
it is an anion, add one
electron for each
1. Find the sum of

valence electrons of
negative charge.
Keep track of the • If it is a cation, subtract
one electron for each
electrons: 5 + 3(7) = 26 positive charge.

Writing Lewis Structures


2. The central atom is
the least
electronegative
element that isn’t
hydrogen. Connect
the outer atoms to it
by single bonds.
Keep track of the electrons:

26 − 6 = 20
Writing Lewis Structures

3. Fill the octets of the


outer atoms.

Keep track of the electrons:


26 − 6 = 20; 20 − 18 = 2
Writing Lewis Structures
4. Fill the octet of the
central atom.

Keep track of the electrons:


26 − 6 = 20; 20 − 18 = 2; 2 − 2 = 0
Worked Example 1.1
Predicting the Number of Bonds to Atoms in a
Molecule
How many hydrogen atoms does phosphorus bond to
in phosphine, PH??
Worked Example 1.1
Predicting the Number of Bonds to Atoms in a
Molecule
Strategy
• Identify the periodic group of phosphorus, and tell
from that how many electrons (bonds) are needed
to make an octet.
Worked Example 1.1
Predicting the Number of Bonds to Atoms in a
Molecule
Solution
• Phosphorus, like nitrogen, is in group 5A of the
periodic table and has five valence electrons. It
thus needs to share three more electrons to make
an octet and therefore bonds to three hydrogen
atoms, giving PH3.
Seatwork
Draw electron dot structure and line-bond structures
for the following substances, showing all nonbonding
electrons:

• (a) CH3CH2OH, ethanol


• (b) H2S, hydrogen sulfide
• (c) CH3NH2, methylamine
• (d) N(CH 3) 3, trimethylamine

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