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I. Chemical Bonding and Electronic Structure

Electronic configuration and valence
1. Aufbau principle
2. Valence shell and core shells
3. Noble gas configuration and 8 electron rule
Covalent vs ionic bonding
1. Definition of terms
2. Electron count in covalent bonds
3. Multiple covalent bonds
Atomic orbitals and hybridization
1. VSEPR principle and bonding geometry
2. Tetrahedral geometry and atomic orbitals
3. Hybridization of atomic orbitals
4. sp³, sp² and sp hybridization of carbon
5. inclusion of lone pairs in VSEPR model
Sigma and \(\pi\) bonding
Electronegativity and polarization of covalent bonds
Resonance
Formal charge, hypovalency and hypervalency
Conjugation of \(\pi\) electrons
Aromaticity

II. Functional groups and Nomenclature

Hydrocarbons
1. Alkanes
2. Cycloalkanes
3. Alkenes, dienes and polyenes
4. Alkynes
5. Arenes
Haloalkanes
Ethers, Sulfides and Epoxides
Amines
Alcohols
Carbonyls
1. Aldehydes
2. Ketones
Carboxylic acids
Carboxylic acid derivatives
1. Esters
2. Amides
3. Acid Halides
4. Anhydrides
5. Nitriles
6. Imides
Esters of inorganic acids: phosphates, sulfates, nitrates
IUPAC rules for nomenclature
1. Hydrocarbon rules
2. Unsaturation
3. Functional group prioritization
4. Suffixes and substituent names for functional groups

III. Stereochemistry

Definition of terms: stereoisomer, chirality, conformation, configuration
Conformational isomerism
1. alkanes
2. cyclohexane
3. substituted cyclohexane
Molecular chirality and optical activity
Configurational isomerism
1. Stereogenic carbon and the Cahn-Ingold-Prelog system
2. Enantiomers and diastereomers
3. E and Z alkenes
4. cis- and trans- disubstituted cycloalkanes
5. Stereogenicity in atoms other than carbon

IV. Intermolecular interactions and physical properties

Boiling point and melting point
1. Effect of molecular weight
2. Polarity and dipole-dipole interactions
3. Hydrogen bonding interactions and their effect
Solubility
1. Solvent-solute interactions
2. Dipole-dipole
3. Hydrogen bonding
4. The hydrophobic effect
Chromatography
1. Exploitation of intermolecular interactions
2. Common stationary phases: silica and alumina
3. forms: TLC, column, HPLC and size exclusion

V. Reactive intermediates: carbocations, carbanions, free radicals

Carbocations
1. Trivalent carbon
2. Lack of an octet
3. sp2 hydridization
4. empty p orbital
5. Stability trends
6. Resonance stabilization
  1. By neighboring \(\pi\) electrons
  2. By neighboring heteroatoms with lone pairs
Carbanions
1. Lone pair on carbon
2. Retention of geometry
3. Configurational lability
4. Stability trends
Free radicals
1. Lack of an octet on C
2. Neutrality of free radicals
3. Stability trends

VI. Spectroscopy

Infrared
1. Theory
2. Symmetry, dipole moments and intensity
3. Characteristic stretching frequencies
4. Bending and other vibrational motion
Mass spectrometry
1. Theory
2. Ionization methods
3. Fragmentation reactions
  1. alpha cleavage
  2. beta cleavage
  3. McLafferty rearrangement
  4. Isoto\(\pi\)c distribution
NMR
1. Theory
2. Chemical shift, deshielding and electronegativity
3. Diamagnetic anisotropy
4. Vicinal coupling
  1. Idea
  2. Coupling constant
  3. Multiplicity (N+1 rule)
  4. Effects of geometry on coupling constant
5. Geminal and 4-bond coupling
6. 13C NMR
7. Other nuclei (15N, 31P, 19F)
Integrated spectroscopy problems

VII. Reactivity and the movement of electrons

Lewis acids and bases; nucleophiles and electrophiles
Definition of terms: addition, elimination, substitution
Donation of electrons toward covalent bond
Use of curved arrow formalism to describe electron movement
1. Starts at reactive lone pair (or bond)
2. Terminates at midpoint of forming bond
3. Alternatively, ends at atom if changing charge state
Curved arrows in resonance
Kinetics and Thermodynamics
1. Reversibility and irreversibility
2. Le Chatelier’s Principle
3. Kinetics and transition state energies
4. Hammond’s postulate and the use of intermediates

VIII. Acid-Base Reactivity

Lewis acidity/basicity vs. Brønsted acidity/basicity
Factors affecting Brønsted acidity
1. Electronegativity
2. Bond strength to hydrogen
3. Inductive effects
4. Resonance effects
5. Solvent effects
Quantifying acidity: pKa values
Representative pKa values of various functional groups
Solvents and the leveling effect