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Representation of Molecules: Structural Formulas

All representations of the same molecule!
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Interpreting Dash Formulas
Are these different or identical compounds?
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Writing Molecular Formulas: Dash and Condensed
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Writing Molecular Formulas: Dash and Condensed
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Writing Molecular Formulas
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Writing Molecular Formulas
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Writing Molecular Formulas
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Three-Dimensional Formulas
ethane
ethane rotated by 90
Solid wedges point out of the plane of the paper; dashed wedges point into the plane of the paper
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Representation of Molecules: Electrostatic Potential Maps
dimethyl ether Electrostatic Potential Map of dimethyl ether
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Representation of Molecules: Electrostatic Potential Maps
Electrostatic potential maps are often placed over ball-and-stick models
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Constitutional Isomers
C
3
H
6
O C
3
H
6
O
Constitutional isomers have different physical properties: MP, BP, and densities and
different chemical properties (reactivity)
Acetone (nail polish remover) Propylene oxide (food thickener)
12 12
Double Bond Rotational Barrier and Cis/Trans Isomerism
Single bonds can rotate freely; double bonds cant rotate freely
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Double Bond Rotational Barrier and Cis/Trans Isomerism
C
2
H
2
Cl
2
C
2
H
2
Cl
2

These compounds have identical molecular formulas but are different
14
Double Bond Rotational Barrier and Cis/Trans Isomerism
Cis Trans
Cis/trans isomers are stereoisomers (isomers that differ in their orientation in space)
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Constitutional Isomers and Cis/Trans Isomer
Constitutional Isomers
Cis/Trans Isomers
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Resonance Structures
17
Resonance Structures
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Resonance Structures
Doubled-headed arrows do NOT represent an equilibrium!
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Resonance Structures
How many single bonds and double bonds would we expect to find in the structure
of the real molecule?
Experimental studies show that all bonds
in the real structure are of equal length!
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Representation of Resonance Hybrid
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True bonding structure can be represented as a resonance hybrid
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Resonance Theory
1) When we can write multiple Lewis structures, none of the structures will be
a completely accurate representation of the molecule.
2) The real structure of the molecule is actually a hybrid of all the resonance
structures.

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-

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Resonance gives us clues about structure and in chemistry structure influences reactivity!
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Resonance Theory and the Real Structure of Molecules
Electrostatic potential map of the carbonate ion
Resonance structures exists only on paper!
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Rules for Writing and Using Resonance Structures
Only move pi electrons or lone pair electrons; never break sigma bonds
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Rules for Writing and Using Resonance Structures
Never break sigma bonds!
X
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Rules for Writing and Using Resonance Structures
Never have an expanded octet on carbon or other second period heteroatoms!
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Second Period Elements and the Octet Rule


Second Period Elements Cant have Expanded Octets!
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Exceptions to the Octet Rule: Expanded Octets


Third period elements (and beyond) can have expanded octets
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Exceptions to the Octet Rule: Incomplete Octets


Elements with incomplete octets are very reactive!