Organic Chemistry I Past Lecture Slides

Lecture 1
Main topics include:
• Syllabus
• i>clicker & OWL registration
• website
• define organic chemistry
• orbitals (Schrodinger equation)
• valence electrons
• models of bonding
• bond-line formulas
The following lecture slides were presented during previous Organic Chemistry I classes. If you are a current orgo I student using these slides to prepare for class, note that several changes may be made to the slides presented this semester. Also, the topics may not be presented in the same order.

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Lecture 2
Main topics include:
• review: 3 models of bonding
• molecular orbital (MO) theory
• valence electrons and formal charge
• drawing bond-line structural formulas
• resonance structures
• curved arrow notation
• determining major resonance contributors
Lecture 3
Main topics include:
• Arrenhius, Bronsted and Lewis acids
• conjugate pairs
• pKa scale
• structural effects on acidity: electronegativity, bond strength, resonance
• resonance contributors effect
• determining Keq from pKas
• Lab: polarity
Lecture 4
Main topics include:
• Skillbuilder 1
Lecture 5
Main topics include:
• Classes of hydrocarbons
• Hybridization (sp3)
• Bonding (VB) in hydrocarbons
• IUPAC nomenclature of alkanes
• Physical properties of alkanes: bp
• Van der Waals forces, London dips.
• Polarizability
• Chemical properties: combustion
Lecture 6
Main topics include:
• sp2 and sp hybridization
• sigma bonds, pi bonds
• conformational isomers (tree)
• Newman, dash-wedge, sawhorse proj.
• eclipsed vs. staggered conformations
• eclipsed, gauche, anti relationships
• steric argument for conformer NRG
• hyperconjugation argument
Lecture 7
Main topics include:
• conformational analysis of butane
• configurational stereoisomers
• cycloalkanes: naming, angle strain
• conformations of cycloalkanes
• 1,3-diaxial interactions
• chair and boat, drawing
• cyclohexane ring inversion
• relative stability of cis and trans configurational isomers of cyclohexane
Lecture 8
Main topics include:
• Skillbuilder 2
• chirality
• chirality centers, asymmetric carbon
• symmetry tests for chirality
• chirality centers of N, S and P
• enantiomers
• R/S-notation for chirality centers
• stereogenic center vs. chirality center
Lecture 9
Main topics include:
• Physical props. of enantiomers
• optical rotation
• demo: homemade polarimeter
• enantiomeric excess (ee) and [a]
• diastereomers and properties
• mess forms
• determining total number of stereoiosmers
• rxns that produce stereoisomers
Lecture 10
Main topics include:
• spectroscopy vs. spectrometry
• mass spectrometry, spectrometer
• Lorentz forces, right-hand rule
• MS spectrum: base peak, M+ and M+1
• infrared spectroscopy, electromagnetic
• stretching, bending movements, dipoles
• wave numbers, areas of IR spectrum
• examples of IR functional groups
Lecture 11
Main topics include:
• IR of functional groups
• EWG and EDG effect of IR of carbonyls
• nuclear magnetic resonance, theory
• chemical shift scale, TMS
• structural effects: EN, #Hs, anisotropy
• examples of NMR spectra and structural effect on chemical shift value
Lecture 12
Main topics include:
• H-NMR equivalency and # signals
• homotopic, enantiotopic, diastereotopic, heterotopic H-atoms
• test for equivalency
• multiplicity, spin-spin splitting
• n+1 rule
Lecture 13
Main topics include:
• complex multiplicities
• splitting trees
• coupling constant (J-value)
• peak distortion (leaning)
• 13C-NMR
• DEPT
• Practice
• Skillbuilder 3
Lecture 14
Main topics include:
• intro to alcohols and alkyl halides
• nomenclatures of alcohols and halides
• physical properties: polarity, bp
• intro to chemical reactions
• bond dissociation energies (BDE)
• calculating enthalpy of reaction
• reaction coordinate diagrams, Ea
• intermediates and transition states
Lecture 15
Main topics include:
• reactivity of alcohols
• reactivity of hydrogen halides
• SN1 mechanism, carbocations
• carbocation stability: inductive effect and hyperconjuation
• Hammond postulate
• transition state energies
• SN2 mechanism and rate laws
Lecture 16
Main topics include:
• nucleophiles and electrophiles
• definition and examples
• examples of SN2 with various nucs.
• reactivity of halide leaving groups
• stereochemistry of SN2; stereospecific
• steric effects on the rate os SN2
• strength of nucleophiles; nucleophilicity
Lecture 17
Main topics include:
• review SN1 and SN2
• solvolysis; SN1 and SN2 with neutral
• carbocation stabiliti: resonance effect
• carbocation stability: solvent effect on the rate of SN1
• polar aprotic solvents: rates SN2
• stereochemistry of SN1: ion pairs
• sulfonate leaving groups; prep.
• halogenation of alkanes; Hammond
Lecture 18
Main topics include:
• review alkene structure and hybridize
• review IHD
• E/Z nomenclature; naming alkenols
• CIP priority review
• stability of alkenes; heat of combustion
• cis vs trans stability
• intro to B-eliminations
Lecture 19
Main topics include:
• mechanism of E1 & E2 dehydration
• carbocation rearrangements
• E2 dehydrohalogenation
• reactivity and mechanism
• anti elimin. for dehydrohalogenation: torsional strain and hyperconjugation
• stereospecific E2
Lecture 20
Main topics include:
• addition reactions to alkenes
• hydrogenation; stereoselectivity
• Markovnikov addition of HX
• peroxide effect; anti-Markovnikov
• addition of H2SO4 to alkenes
• hydration of alkenes
Lecture 21
Main topics include:
• Addendum: Competition between substitution and elimination;
• Hydroboration-Oxidation
• Halogenation; vicinal halohydrins
• Rates of addition to alkenes
• ozonolysis
• dihydroxylation
• epoxidation
• synthesis; retrosynthetic analysis
Lecture 22
Main topics include:
• Alkynes: physical and chemical props.
• alkyne acidity; common bases
• alkylation of alkynes with alkyl halides
• double dehydrohalogenation
• addition reactions of alkynes: HX, hydration by Hg2+, halogenation,
• hydrogenation; Lindlar catalyst (cis)
• dissolving metal reduction (trans)
Lecture 23
Main topics include:
• Conjugated Systems
Lecture 24
Main topics include:
• Addition reactions to conjugated dienes
Lecture 25
Main topics include:
• Constructing the HOMO and LUMO of conjugated systems
• Symmetry allowed cycloaddition
• Benzene: observations of aromaticity
• Constructing MOs of benzene
• Defining aromaticity as closed shell for cyclically conjugated systems
Lecture 26
Main topics include:
• MO diagrams of aromatic systems
• Frost Circle; Antiaromatic systems
• Consequences of aromatic: tropylium
• Reactions of benzylic carbons: styrenyl additions; halogen., SN1, SN2, E1, E2
• Clemensen and Wolf-Kishner
• Hydrogenation of benzylic ketones
• KMnO4 oxidation of benzylic carbons
• review of redox definitions
Lecture 27
Main topics include:
• Electrophilic aromatic substitution
• arenium ions
• nitration, sulfonation, bromination
• Friedel-Crafts alkylation and acylation
• rate of SE-Ar with EDGs and EWGs
• ortho/para directors
• meta directors
Lecture 28
Main topics include:
• Electrophilic aromatic substitution
• arenium ion resonance structures
• ortho/para direction explained
• meta direction explained
• synthesis with SE-Ar
• classification of activating/deactivating groups
• amines vs. amide activation