MCAT Org. Chem Ch. 3
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| Quantum Numbers | Describe the size, shape, orientation, and nnumber of atomic orbitals that an element possesses
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| Principal Quantum Number, n | Describes the energy level (shell) in which an electron resides and indicates the distance from the nucleus to the electron. Its possible values range from 1 to inf.
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| Azimuthal Quantum Number, l | Determines the subshell in which an electron resides. Possible values range from 0 to n-1. Subshell indicated with a letter: l = 0 means s, 1 = p, 2 = d, 3 = f
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| Magnetic Quantum Number, ml | Determines the orbital in which an electron resides. Possible values range from -l to l. Different orbitals have different shapes: s-orbitals are spherical, while p-orbitals are dumbbell-shaped and located on the x-, y-, or z-axis
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| Spin Quantum Number, ms | Describes the spin of an electron. Possible values = +1/2
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| Bonding Orbitals | Created by head-to-head or tail-to-tail overlap of atomic orbitals of the same sign and are energetically favorable.
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| Antibonding Orbitals | Created by head-to-head or tail-to-tail overlap of atomic orbitals that have opposite signs and are energetically unfavorable.
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| Single Bonds | Sigma bonds which contain two electrons.
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| Double Bonds | Contain one sigma bond and one pi bond. Pi bonds are created by sharing electrons between two unhybridized p-orbitals that align side-by-side.
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| Triple Bonds | Contain one sigma bond and two pi bonds.
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| Note About Flexibility of Multiple Bonds vs. Single Bonds | Multiple bonds are less flexible because rotation is not permitted in the prescence of a pi bond.
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| Strength of Multiple Bonds vs. Single Bonds | Multiple bonds are shorter and stronger.
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| Strength of Individual Pi and Sigma Bonds | Individual pi bonds are weaker than sigma bonds.
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| sp3-hybridized orbitals | Orbitals that have 25% s character and 75% p character. They form tetrahedral geometry with 109.5 degree bond angles. Carbons with all single bonds are sp3-hybridized.
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| sp2-hybridized orbitals | Orbitals have 33% s character and 67% p character. They form trigonal planar geometry with 120 degree bond angles. Carbons with one double bond are sp2-hybridized.
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| sp-hybridized orbitals | Orbitals that have 50% s character and 50% p character. They form linear geometry with 180% bond angles. Carbons with a triple bond, or with two double bonds, are sp-hybridized.
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| Resonance | Delocalization of electrons in molecules that have conjugated bonds
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| Conjugation | Occurs when single and multiple bonds alternate, creating a system of unhybridized p-orbitals down the backbone of the molecule through with pi electrons can delocalize.
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| Note About Resonance And Stability Of A Molecule | Resonance increases the stability of a molecule
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| Note About Electron Density And Stability Of Resonant Molecule Forms | The more stable the resonance form, the more the molecule contributes electrons.
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| Note About Which Resonant Forms Are Favored | Favored forms are ones that lack formal charge, form full octets on electronegative atoms, or stabilize charges through induction and aromaticity.
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