ORGANIC - SMITH 5E

CH. 1 - STRUCTURE AND BONDING (PART 1)

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ORGANIC - SMITH 5E
CH. 1 - STRUCTURE AND BONDING (PART 1)
CONCEPT: WHAT IS ORGANIC CHEMISTRY?
Organic Chemistry is the chemistry of life. It consists of the study of molecules that are (typically) created and used by
biological systems.
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Creating Nerve Gases

Technically, an organic molecule is any molecule that contains both Carbon and Hydrogen.
An organic molecule that contains a mixture of carbon and hydrogen solely is called a Hydrocarbon.
EXAMPLE: Which molecules are organic? Which of them are also hydrocarbons?

Organic: C & H
Hydrocarbon: C & H only
Methane: CH4
Simplest Hydrocarbon

Organic: C & H
Not Hydrocarbon: Has O
Acetone: (CH3)2CO

Not Organic: No H
Not Hydrocarbon: Has O
Carbon Dioxide: CO2
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ORGANIC - SMITH 5E
CH. 1 - STRUCTURE AND BONDING (PART 1)
CONCEPT: ATOMIC STRUCTURE
The atom is the basic unit of matter.
The atomic number of an atom is equal to the number of Protons
The mass number of an atom is equal to
Protons + Neutrons
Isotopes have the same atomic number but have differing Neutrons
EXAMPLE: Hydrogen Isotopes

Represented by "D"

Represented by "T"

Electrons orbit the nucleus in a region of space that is called a Shell

The region of space within a shell with exactly enough space for a pair of electrons (up/down spin) is called an Orbital
When atoms possess a different number of electrons than protons, they are called Ions
Positively charged atoms are called Cation Negatively charged atoms are called Anion

EXAMPLE: Hydrogen Ions

Three Principles of Electron Configuration

"Building up"

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ORGANIC - SMITH 5E
CH. 1 - STRUCTURE AND BONDING (PART 1)
PRACTICE: Determine the number of protons, neutrons and electrons in the following atoms.
a.

b.

PRACTICE: Determine which of the three principles of electron configuration is being broken in the electron diagrams below.
c.
Hund's Rule

d.

Aufbau Principle

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ORGANIC - SMITH 5E
CH. 1 - STRUCTURE AND BONDING (PART 1)
CONCEPT: WAVE FUNCTIONS
Quantum Mechanics states that electrons behave both as particles and as Waves.
The Heisenberg Uncertainty Principle states that we cannot simultaneously know an electrons speed and Position
Equations called wave functions correspond to energy state the energy state for a given electron (psi : greek)
The relative probability of finding an electron can be derived from the wave function 2
The 3-D plot of the 2 is called an atomic Orbital : where the chance of finding electrons is high.
2e

2e

2e

2e

2e

Carbon: 6e

2e Total

8e Total

As with any type of wave, wave functions have the ability to Interfere with each other upon meeting.
This can occur either constructively or destructively
EXAMPLE: H2 Molecular Orbitals

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ORGANIC - SMITH 5E
CH. 1 - STRUCTURE AND BONDING (PART 1)
CONCEPT: MOLECULAR ORBITALS
When atomic orbitals overlap constructively, they create unusual regions of shared electron density called Bonds
The type of bond created is determined by how many regions are overlapping
s

Double Bonds has a bond in it

Single

We can use a model called the Linear Combination of Atomic Orbitals (LCAO) using addition and subtraction of orbitals to
indicate the type of interference. This way we can determine the mathematical energy levels of all possible molecular orbitals.
EXAMPLE: H2 LCAO
Molecular Orbital

Atomic
Orbital

Atomic
Orbital
Molecular Orbital

EXAMPLE: C2 LCAO (simplified)

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ORGANIC - SMITH 5E
CH. 1 - STRUCTURE AND BONDING (PART 1)
CONCEPT: BOND SUMMARY

EXAMPLE: Determine the number of -bonds and -bonds in the following molecules

a.

b.

PRACTICE: Rank the following bonds from shortest to longest

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ORGANIC - SMITH 5E
CH. 1 - STRUCTURE AND BONDING (PART 1)
CONCEPT: THE OCTET RULE
Atoms are most stable when they achieve the number of electrons necessary to reach a Nobel Gas Configuration.

The tendency for atoms to lose or gain electrons in order to reach this configuration is known as the __________ rule

We can use MO theory to prove why atoms are most stable (and will not form bonds) in the Nobel gas configuration
EXAMPLE: He2 LCAO

Atoms can satisfy their octet through forming chemical bonds or by possessing lone pairs. These are called octet electrons.
First-row elements (H, He, Li) will prefer to possess _____ octet electrons
Second-row elements (C, N, O, F) will prefer to possess _______ octet electrons
Atoms smaller than Carbon will possess less than 8 electrons: (Be) ______ and (B) ________
Third-row elements may form expanded octets that can hold (P) _____ and (S) _______
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ORGANIC - SMITH 5E
CH. 1 - STRUCTURE AND BONDING (PART 1)
PRACTICE: Analyze the following molecules. Circle ALL atoms that are in violation of the octet rule.

a.

b.

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ORGANIC - SMITH 5E
CH. 1 - STRUCTURE AND BONDING (PART 1)
CONCEPT: BONDING PREFERENCES
There may be many ways to combine octet electrons to satisfy the octet rule for a certain atom:
_________________ electrons are the name we give to the octet electrons that the atom actually owns. The number of
these determines which of the possible octets will be the most stable.
An atom owns every lone electron it has
An atom owns ___ electron for every bond that it has
EXAMPLE: Find the total number of octet electrons and valence electrons in the following hydrocarbons. Do all of these
compounds satisfy the octet rule? If so, are they all equally stable?

The amount of electrons that the valence shell of each 2nd row element prefers to own is determined by its group number
on the periodic table. This will determine how many bonds it wants to have in its most stable state.

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ORGANIC - SMITH 5E
CH. 1 - STRUCTURE AND BONDING (PART 1)
CONCEPT: FORMAL CHARGES
Whenever there is a difference between the number of valence electrons that an atom has and its group number, a formal
charge is assigned.
FORMAL CHARGE = Group # - Valence Electrons

The __________________ is the term that we give to the SUM of all the formal charges of a molecule.
EXAMPLE: Calculate the formal charges of ALL atoms.

PRACTICE: Calculate the formal charges of ALL atoms. Indicate if the molecule has a net charge.

a.

b.

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ORGANIC - SMITH 5E
CH. 1 - STRUCTURE AND BONDING (PART 1)
CONCEPT: BONDLINE STRUCTURES
The bondline method is a way to simplify the drawings of organic structures, based on the octet rule.
_____________ are implied: Every corner is assumed to represent a carbon.
_____________ are implied: Carbon is assumed to possess enough hydrogens to fill its octets.
_____________ are implied: Heteroatoms are assumed to possess enough electrons to fill their octets.
____________ _____________ are used to indicate when an atom does not satisfy its bonding preference.
Watch Out: ALL hydrogens on ______________________________ MUST be drawn explicitly.
EXAMPLE: Conversion of ethanol to bondline

PRACTICE: How many implied hydrogens does each labeled carbon have?

a.

b.

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ORGANIC - SMITH 5E
CH. 1 - STRUCTURE AND BONDING (PART 1)
PRACTICE: Convert each structure into a line-angle structure. Be sure to assign ALL necessary formal and net charges.

a.

b.

c.

d.

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