Organic Chemistry Ch 3. Bonding Flashcards
Quantum numbers
Describe the size, shape, orientation, and number of atomic orbitals an element possesses
Atomic orbitals
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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, possible values range from 1 to infinity
Azimuthal quantum number
l - determines the substsell in which an electron resides, values range from 0 to n-1,, subshell also often indicated with a letter l=0=s, l=1=p, l=2=d, l=3=f
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 are spherical, p are dumbbell shaped and located on x,y, or z axis
Spin quantum number
ms - describes the spin of an electron, possible values are +/- 1/2
Bonding orbitals
Created by head to head or tail to tail overlap of atomic orbitals of the same sign and are energetically favorable
Antibonding orbitals
Created by head to head or tail to tail overlap of atoms orbitals that have opposite signs and are energetically unfavorable
Single bonds
Sigma bonds that contain 2 electrons
Sigma bonds
Contain 2 electrons
Double bonds
Contain one sigma bond and one pi bond
Pi bonds
Created by the sharing of electrons between two unhybridized p-orbitals that align side by side
Triple bonds
Contain one sigma and two pi bonds
Bond length
Multiple bonds are shorter and stronger than single bonds
Bond flexibility
Multiple bonds are less flexible than single bonds because rotation is not permitted in the presence of a pi bond
Bond strength
Multiple bonds are stronger than single bonds though sigma bonds are stronger than pi bonds
sp3 hybridization
Has 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
sp2 hybridization
Has 33% s character and 66% p character, they form trigonal planar geometry with 120 degree bond angles, carbons with one double bond are sp2 hybridized
sp hybridization
Has 50% s character and 50% p character, they form linear geometry with 180 degree bond angles, carbons with two double bond or one triple bond are sp hybridized
Resonance
Describes the delocalization of electrons in molecules that have conjugated bonds, increases the stability of a molecule, the various resonance forms all contribute to the true electron density of the molecule, the more stable the resonance form, the more it contributes, forms are favored if they lack formal charge, form full octets on electronegative atoms, or stabilize charts through induction and aromaticity
Conjugation
Occurs when single or multiple bonds alternate, creating a system of unhybridized p-orbitals down the backbone of the molecule through which pi electrons can delocalize