Organic chemistry
Bruices Organic Chemistry: Chapters 1, 2
Learning Outcomes
1. Review and understand electronic structure and
bonding in molecules, particularly compounds
important to organic chemistry (General Chemistry)
2. Review the factors which affect acid-base properties,
bond strengths.
Background
General Chemistry (CHEM1042):
Atomic and electronic structure
Ionic and covalent bonds, dipole moments
Lewis and Kekule structures
Atomic orbitals, hybridization and molecular
geometry (VSEPR theory)
How single, double, triple bonds are
formed
... Reviewed in Bruice Chapter 1
2
Background
General Chemistry (CHEM1042):
Atomic and electronic structure
1. Underlying foundation for all chemical reactions;
2. Electronic structure is the basis for atom
bonding and therefore determines all chemical
reactivities;
Background
H and He
total orbitals: 1 + 3 + 5 = 9
total orbitals: 1 + 3 = 4
total orbitals: 1 + 3 + 5 + 7 = 16
Background
H and He
Background
Aufbau principle: An electron goes into the
atomic orbital with the lowest energy. (Why:
The closer of the electrons to the postitive
nucleus, the lower its energy is.)
Background
Aufbau principle: An electron goes into the
atomic orbital with the lowest energy. (The
closer of the electrons to the nucleus, the
lower the is its energy)
Pauli exclusion principle: No more than two
electrons can be in an atomic orbital and the
two electrons must be of opposite spin.
(Determined by quantum physics)
Background
Background
Aufbau principle: An electron goes into the
atomic orbital with the lowest energy. (The
closer of the electrons to the nucleus, the
lower the is its energy)
Pauli exclusion principle: No more than two
electrons can be in an atomic orbital and the
two electrons must be of opposite spin.
Hunds rule: An electron goes into an empty
degenerate orbital rather than pairing up. (This
minimizes electron repulsion)
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Background
After orbitals are filled, now we need to look at valence
electrons (the ones in the outermost shell).
IMPORTANT: Electrons in inner shells do not participate
in bonding, only outer shell valence electrons do.
valence electrons
1s
Background
Octet rule:
A chemical rule of thumb that reflects observation
that atoms of main-group elements tend to combine
in such a way that each atom has eight electrons in
its valence shell, giving it the same electronic
configuration as a noble gas.
The rule is especially applicable to carbon, nitrogen,
oxygen, and the halogens, but also to metals such as
sodium or magnesium.
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Background
Octet rule:
Explanation for Li+, Na+, F-, Cl-, Br-, I-, H+. H-.
Less than 8 electrons
Br, I
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Background
Octet rule:
Explanation for Li+, Na+, F-, Cl-, Br-, I-, H+. H-.
1s22s22p5
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Background
Octet rule:
Explanation for electron-sharing in covalent
bond to fulfill the rule.
Explanation for different bonds formed by
H, Cl, O, N, and C.
needs to form bonds
(share electrons) to
achieve 8 electrons
O=C=O
Noble gases: Neon (Ne), 1s2 2s2 2p6; already 8 electrons, very stable
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Background
Physical basis of EN:
smaller, more compact atoms
valence
electrons are in
different shells;
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Background
Electronegativity (EN)
no sharing
equal sharing
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Background
ionic
too separated
equal sharing
too stable
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Background
Background
General Chemistry (CHEM1042):
Atomic and electronic structure
Ionic and covalent bonds, dipole moments
Lewis and Kekule structures
Atomic orbitals, hybridization and molecular
geometry (VSEPR theory)
How single, double, triple bonds are
formed
... Reviewed in Bruice Chapter 1
20
Organic Compounds
Organic compounds are those based on carbon
Why separate out carbon-containing compounds out of
all of the other 100+ elements as a special category?
Carbon is relatively abundant
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DOUBLE BOND
TRIPLE BOND
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1s22s22p63s23p33d0
1s22s22p6
EN: 2.1
EN: 2.5
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