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Chemistry LibreTexts

Course Content

I. Chemical Bonding and Electronic Structure

  1. Electronic configuration and valence
    1. Aufbau principle
    2. Valence shell and core shells
    3. Noble gas configuration and 8 electron rule
  2. Covalent vs ionic bonding
    1. Definition of terms
    2. Electron count in covalent bonds
    3. Multiple covalent bonds
  3. 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
  4. Sigma and \(\pi\) bonding
  5. Electronegativity and polarization of covalent bonds
  6. Resonance
  7. Formal charge, hypovalency and hypervalency
  8. Conjugation of \(\pi\) electrons
  9. Aromaticity

II. Functional groups and Nomenclature

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

III. Stereochemistry

  1. Definition of terms: stereoisomer, chirality, conformation, configuration
  2. Conformational isomerism
    1. alkanes
    2. cyclohexane
    3. substituted cyclohexane
  3. Molecular chirality and optical activity
  4. 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

  1. Boiling point and melting point
    1. Effect of molecular weight
    2. Polarity and dipole-dipole interactions
    3. Hydrogen bonding interactions and their effect
  2. Solubility
    1. Solvent-solute interactions
    2. Dipole-dipole
    3. Hydrogen bonding
    4. The hydrophobic effect
  3. 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

  1. 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
  2. Carbanions
    1. Lone pair on carbon
    2. Retention of geometry
    3. Configurational lability
    4. Stability trends
  3. Free radicals
    1. Lack of an octet on C
    2. Neutrality of free radicals
    3. Stability trends

VI. Spectroscopy

  1. Infrared
    1. Theory
    2. Symmetry, dipole moments and intensity
    3. Characteristic stretching frequencies
    4. Bending and other vibrational motion
  2. Mass spectrometry
    1. Theory
    2. Ionization methods
    3. Fragmentation reactions
      1. alpha cleavage
      2. beta cleavage
      3. McLafferty rearrangement
      4. Isoto\(\pi\)c distribution
  3. 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)
  4. Integrated spectroscopy problems

VII. Reactivity and the movement of electrons

  1. Lewis acids and bases; nucleophiles and electrophiles
  2. Definition of terms: addition, elimination, substitution
  3. Donation of electrons toward covalent bond
  4. 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
  5. Curved arrows in resonance
  6. 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

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