The Bonding is part of the Organic Chemistry section which provides High Yield information for the MCAT and Medical School, Residency, and in the future career as a Physician. Prepare and Learn Ahead! Educating, Preparing, and Proving high-yield content, quizzes, and medical resources. to students who are interested in the medical field.
Atomic Orbitals and Quantum Numbers
- Principle Quantum Number, n: Corresponds to the energy level of a given electron in an atom. Basically a measure of size. The smaller the number, the closer the shell is to the nucleus.
- Azimuthal Quantum number, l: describes the subshells which are within each electron shell. l ranges from 0 to n-1.
- 0 corresponds to the s subshell which is spherical and symmetric
- 1 corresponds to the p subshell which is composed of two lobes located symmetrically about the nucleus and contains there is a node (zero probability)
- 2 corresponds to the d subshell are four symmetrical lobes and have two nodes. Shapes are usually not tested.
- 3 corresponds to the f subshell
- Energy increases as l increases
- Magnetic Quantum Number, ml: describes the orbitals within the subshell. Ranges from –l to +l.
- Spin Quantum Number, ms: distinguishes the spin on the electrons in each orbital: ± 1/2
Molecular Orbitals
- When two atomic orbitals combine, they form molecular orbitals.
- If the signs of the wave function are the same, then a lower energy bonding orbital is produced.
- If the signs are different, a higher energy antibonding orbital is produced.
Sigma and Pi Bonds (bonding)
- Sigma Bonds: when a molecular orbital is formed by head-to-head or tail-to-tail overlap
- All single bonds are sigma and they accommodate two electrons.
- Pi Bonds: when two p-orbitals line up in parallel (Side-by-side)
- One Pi bond on top of an existing sigma bond is a double bond
- A sigma bond and two pi bonds forms a triple bond
- Double and triple bonds hinder rotation and lock the atoms in position.
- Cannot exist independently of a sigma bond
- Double bonds are shorter than single bonds and thus are stronger
- Pi bonds are weaker than Sigma bonds and will be broken first in order to turn a double bond into a single bond
- Double bonds make for stiffer molecules
Hybridization
- Hybrid Orbitals: formed by mixing different types of orbitals
sp3
- Four orbitals point towards different vertices of a tetrahedron, which is why carbons prefer this geometry.
- Most common type of hybridization for carbon.
- If asked for how much “s character” a certain hybrid has. Simply look at the name and use it to solve the problem. Sp3 would have 25% s character and 75% p character
Sp2
- One s orbital is mixed with two p
- Hybridization seen in alkenes
- Third p-orbital is left unhybridized, this orbital participates in pi bonds.
- Three hybridized sp2 orbitals are 120 degrees apart from each other
Sp
- Hybridization for molecules with triple bonds: two p-orbitals are for pi bonds (unhybridized) while the third p orbital combines with the s orbital to form two sp-orbitals
- sp hybridized orbitals are oriented 180 degrees apart
Resonance
- Resonance delocalization of electron occurs in molecules that have conjugated bonds
- Conjugation: alternating single and multiple bonds
- This pattern aligns a number of unhybridized p-orbitals down the backbone of the molecule
- p electrons can then delocalize through the p-orbital system, which adds stability to the molecule.
- True electron density will favor the most stable form (lacks formal charges, or form full octets on highly electronegative atoms).
- The true form of a molecule is a hybrid of the multiple resonance structures.
