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1 Organic Chemistry
The study of carbon-containing molecules and their reactions What happens to a molecule during a reaction?
A collision Bonds break/form
WHAT IS A BOND?
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What term do we use to describe different substances with the same formula?
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Lets look at a specific formal charge example. Given the Lewis structure, calculate the formal charge on each atom. or
Carbon should have 4 valence e-s, because it is in group IVA on the periodic table. Carbon actually has 8 valence e-s. It needs 8 for its octet, but only 4 count towards its charge. WHY? The 4 it actually has balance out the 4 it should have, so it does not have formal charge. Its neutral.
Copyright 2012 John Wiley & Sons, Inc.
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Lets look at the formal charge of the oxygen atom. or Oxygen should have 6 valence e-s, because it is in group VIA on the periodic table. It actually has 8 valence e-s. It needs 8 for its octet, but only 7 count towards its charge. WHY? If it actually has 7, but it should only have 6, what is its formal charge? Practice with skill builder 1.4
Copyright 2012 John Wiley & Sons, Inc.
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Covalent bonds are electrons pairs that exist in an orbital shared between two atoms. What do you think that orbital looks like? Just like an atomic orbital, the electrons could be anywhere within that orbital region. What factors determine which atom in the bond will attract the shared electrons more?
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Nonpolar Covalent bonded atoms share electrons evenly Polar Covalent One of the atoms attracts electrons more than the other
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Electrons tend to shift away from lower electronegativity atoms to higher electronegativity atoms.
The greater the difference in electronegativity, the more polar the bond.
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In this p-orbital, there is a nodal plane. The sign of the wavefunction will be important when we look at orbital overlapping in bonds.
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H2 MOs
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When the AOs overlap, why do the electrons go into the bonding MO rather than the antibonding MO?
Copyright 2012 John Wiley & Sons, Inc.
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Depending on the circumstances, we will use both MO and valence bond theory to explain phenomena.
Copyright 2012 John Wiley & Sons, Inc.
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If four H atoms were to come in and overlap with the 2s and 2p orbitals, what geometry would the resulting methane have?
Copyright 2012 John Wiley & Sons, Inc.
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Should the shape of an sp3 orbital look more like an s or more like p orbital?
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Draw a picture that shows the necessary atomic orbitals and their overlap to form water.
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Each carbon in ethene must bond to three other atoms, so only three hybridized atomic orbitals are needed
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Which should be stronger, an sp3 sp3 sigma bond overlap or an sp sp sigma bond overlap?
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Methane has 4 equal bonds, so the bond angels are equal
3 sp
Geometry
The bond angels in oxygen are even smaller, why?
For any sp3 hybridized atom, the 4 valence electron pairs will form a tetrahedral electron group geometry
How does the lone pair of ammonia affect its geometry?
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3 sp
Geometry
The molecular geometry is different from the electron group geometry. HOW?
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2 sp
Geometry
Calculate the Steric number for BF3 Electron pairs that are located in sp2 hybridized orbitals will form a trigonal planar electron group geometry What will be the molecular geometry?
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2 sp
Geometry
How many electrons are in Borons unhybridized p orbital? Does this geometry follow VSEPR theory?
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2 sp
Geometry
Analyze the steric number, hybridization, electron group geometry and molecular geometry for this imine?
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1.10 sp Geometry
Analyze the Steric number, the hybridization, the electron group geometry, and the molecular geometry for the following molecules BeH2
CO2
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= 1.87 D
Copyright 2012 John Wiley & Sons, Inc.
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= 8.51 x 10-18 esu cm = 8.51 D What % of the C-Cl bond is ionic? Is the C-Cl bond mostly ionic or mostly covalent?
Copyright 2012 John Wiley & Sons, Inc.
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1.12 Dipole-Dipole
Dipole-dipole forces result when polar molecules line up their opposite charges. Note acetones permanent dipole results from the difference in electronegativity between C and O The dipole-dipole attractions BETWEEN acetone molecules affects acetones boiling and melting points. HOW?
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1.12 Dipole-Dipole
Why do isobutylene and acetone have such different MP and BPs?
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Dimethyl sulfoxide
Copyright 2012 John Wiley & Sons, Inc.
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Nonpolar molecules normally have their electrons (-) spread out evenly around the nuclei (+) completely balancing the charge However, the electrons are in constant random motion within their MOs
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Such fleeting attractions are generally weak. But like any weak attraction, if there are enough of them, they can add up to a lot
Copyright 2012 John Wiley & Sons, Inc.
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1.13 Solubility
We use the principle, like-dissolves-like Polar compounds generally mix well with other polar compounds
If the compounds mixing are all capable of H-bonding and/or strong dipole-dipole, then there is no reason why they shouldnt mix
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1.13 Solubility
We know it is difficult to get a polar compound (like water) to mix with a nonpolar compound (like oil)
We cant use just water to wash oil off our dirty cloths
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1.13 Solubility
Soap molecules organize into micelles in water, which form a nonpolar interior to carry away dirt.
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1.13 Solubility
Which attraction is generally stronger?
The attraction between a permanent dipole and an induced dipole or The attraction between a temporary dipole and an induced dipole
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1.13 Solubility
Why wont a nonpolar compound readily dissolve in water? Is it because the water molecules repel the nonpolar molecules?
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