Course Content
- Page ID
- 9603
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)I. Chemical Bonding and Electronic Structure
- Electronic configuration and valence
- Aufbau principle
- Valence shell and core shells
- Noble gas configuration and 8 electron rule
- Covalent vs ionic bonding
- Definition of terms
- Electron count in covalent bonds
- Multiple covalent bonds
- Atomic orbitals and hybridization
- VSEPR principle and bonding geometry
- Tetrahedral geometry and atomic orbitals
- Hybridization of atomic orbitals
- sp3, sp2 and sp hybridization of carbon
- 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
- Alkanes
- Cycloalkanes
- Alkenes, dienes and polyenes
- Alkynes
- Arenes
- Haloalkanes
- Ethers, Sulfides and Epoxides
- Amines
- Alcohols
- Carbonyls
- Aldehydes
- Ketones
- Carboxylic acids
- Carboxylic acid derivatives
- Esters
- Amides
- Acid Halides
- Anhydrides
- Nitriles
- Imides
- Esters of inorganic acids: phosphates, sulfates, nitrates
- IUPAC rules for nomenclature
- Hydrocarbon rules
- Unsaturation
- Functional group prioritization
- Suffixes and substituent names for functional groups
III. Stereochemistry
- Definition of terms: stereoisomer, chirality, conformation, configuration
- Conformational isomerism
- alkanes
- cyclohexane
- substituted cyclohexane
- Molecular chirality and optical activity
- Configurational isomerism
- Stereogenic carbon and the Cahn-Ingold-Prelog system
- Enantiomers and diastereomers
- E and Z alkenes
- cis- and trans- disubstituted cycloalkanes
- Stereogenicity in atoms other than carbon
IV. Intermolecular interactions and physical properties
- Boiling point and melting point
- Effect of molecular weight
- Polarity and dipole-dipole interactions
- Hydrogen bonding interactions and their effect
- Solubility
- Solvent-solute interactions
- Dipole-dipole
- Hydrogen bonding
- The hydrophobic effect
- Chromatography
- Exploitation of intermolecular interactions
- Common stationary phases: silica and alumina
- forms: TLC, column, HPLC and size exclusion
V. Reactive intermediates: carbocations, carbanions, free radicals
- Carbocations
- Trivalent carbon
- Lack of an octet
- sp2 hydridization
- empty p orbital
- Stability trends
- Resonance stabilization
- By neighboring \(\pi\) electrons
- By neighboring heteroatoms with lone pairs
- Carbanions
- Lone pair on carbon
- Retention of geometry
- Configurational lability
- Stability trends
- Free radicals
- Lack of an octet on C
- Neutrality of free radicals
- Stability trends
VI. Spectroscopy
- Infrared
- Theory
- Symmetry, dipole moments and intensity
- Characteristic stretching frequencies
- Bending and other vibrational motion
- Mass spectrometry
- Theory
- Ionization methods
- Fragmentation reactions
- alpha cleavage
- beta cleavage
- McLafferty rearrangement
- Isoto\(\pi\)c distribution
- NMR
- Theory
- Chemical shift, deshielding and electronegativity
- Diamagnetic anisotropy
- Vicinal coupling
- Idea
- Coupling constant
- Multiplicity (N+1 rule)
- Effects of geometry on coupling constant
- Geminal and 4-bond coupling
- 13C NMR
- 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
- Starts at reactive lone pair (or bond)
- Terminates at midpoint of forming bond
- Alternatively, ends at atom if changing charge state
- Curved arrows in resonance
- Kinetics and Thermodynamics
- Reversibility and irreversibility
- Le Chatelier’s Principle
- Kinetics and transition state energies
- Hammond’s postulate and the use of intermediates
VIII. Acid-Base Reactivity
- Lewis acidity/basicity vs. Brønsted acidity/basicity
- Factors affecting Brønsted acidity
- Electronegativity
- Bond strength to hydrogen
- Inductive effects
- Resonance effects
- Solvent effects
- Quantifying acidity: pKa values
- Representative pKa values of various functional groups
- Solvents and the leveling effect