Lecture Slides • Summer 2017

Lecture 1: May 15, 2017
Main topics include:
• Syllabus
• define organic chemistry
• orbitals (Schrodinger equation)
• valence electrons
• models of bonding
• bond-line formulas
• molecular orbital (MO) theory
• valence electrons and formal charge
• drawing bond-line structural formulas
Lecture 1
The following slides were presented during class on the dates indicated. These slides are only made available after the indicated class date. Every effort is made to correct errors found on slides during lecture before posting.

Prelab slides can always be found at the end of the class lecture slides.

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Lecture 2: May 17, 2016
Main topics include:
• valence electrons and formal charge
• resonance structures
• curved arrow notation
• major resonance contributors
• structural effects on acidity: electronegativity, bond strength, resonance
• resonance contributors effect
• determining Keq from pKas
221-2-May19.pdf
Lecture 3: May 18, 2016
Main topics include:
• Arrenhius, Bronsted and Lewis acids
• conjugate pairs; pKa scale
• structural effects on acidity
• resonance contributors effect
• determining Keq from pKas
• hydrocarbons; sp3 hybridization
• bonding, IUPAC and physical properties
• London Dispersion forces
• polarizibility
221-3-May21.pdf
Lecture 4: May 19, 2016
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 energies
• hyperconjugation argument
• conformational analysis of butane
221-4-May21.pdf
Lecture 5: May 20, 2016
Main topics include:• cycloalkanes: naming, angle strain
• conformations of cycloalkanes
• 1,3-diaxial interactions; chair/boat
• cyclohexane ring inversion
• cis/trans configurations of mono and disubstituted cycloalkanes; stability
• chirality
• chirality centers, asymmetric carbon
• symmetry tests for chirality
221-5-May22.pdf
Lecture 6: May 23, 2016
Main topics include:
• enantiomers
• R/S-notation
• stereogenic vs. chirality centers
• Physical props. of enantiomers
• optical rotation
• enantiomeric excess (ee) and [a]
• diastereomers and properties; meso
• determining number of stereoisomers
221-6-May26.pdf
Lecture 7: May 27, 2015
Main topics include:
• spectroscopy vs. spectrometry
• mass spectrometry, spectrometer
• Lorentz forces, right-hand rule
• MS spectrum: base peak, M+ and M+1
• isotopic distribution
• infrared spectroscopy, electromagnetic
• stretching, bending movements, dipoles
• examples of IR functional groups
• skill builder 2
221-7-May24.pdf
Lecture 8: May 25, 2016
Main topics include:
• nuclear magnetic resonance, theory
• chemical shift scale, TMS
• shielding effect
• structural effects: EN, #Hs, anisotropy
• H-NMR equivalency and # signals
• homotopic, enantiotopic, diastereotopic, heterotopic H-atoms
• tests for equivalency
221-8-May25.pdf
Lecture 9: May 26, 2016
Main topics include:
• spin-spin coupling
• complex multiplicities
• splitting trees
• coupling constant (J-value)
• peak distortion (leaning)
• 13C-NMR
• DEPT
• Practice
221-9-May26.pdf
Lecture 10: May 31, 2016
Main topics include:
• intro to alcohols and alkyl halides
• nomenclatures and physical properties
• intro to chemical reactions
• bond dissociation energies (BDE); ∆H
• reaction coordinate diagrams, Ea
• intermediates and transition states
• reactivity of alcohols
• reactivity of hydrogen halides
• Skillbuilder 3
221-10-May31.pdf
Lecture 11: June 1, 2016
Main topics include:
• SN1 mechanism, carbocations
• carbocation stability: inductive effect and hyperconjugation
• Hammond postulate
• transition state energies
• SN2 mechanism and rate laws
• nucleophiles and electrophiles
• examples of SN2 with various nucs.
• reactivity of halide leaving groups
221-11-Jun4.pdf
Lecture 12: June 2, 2016
Main topics include:
• stereochemistry of SN1 and SN2
• steric effects on the rate os SN2
• strength of nucleophiles; nucleophilicity
• review SN1 and SN2 mechanism
• solvolysis; SN1 and SN2 with neutral nut
• carbocation stabilitiy: resonance effect
• carbocation stability: SN1 solvent effect
• polar aprotic solvents: SN2 solvent effect
• sulfonate leaving groups; preparation
221-12-Jun2.pdf
Lecture 13: June 6, 2016
Main topics include:
• radical halogenation; regioselectivity
• 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
• mechanism of E1
221-13-Jun6.pdf
Lecture 14: June 7, 2016
Main topics include:
• mechanism of E1 & E2 dehydration
• carbocation rearrangements
• E2 dehydrohalogenation
• reactivity and mechanism
• anti elimin. for dehydrohalogenation: torsional strain and hyperconjugation
• Hoffman vs. Zaitsev products; TSs
• Competition between substitution and elimination; conditions
221-14-Jun9.pdf
Lecture 15: June 8, 2016
Main topics include:
• hydrogenation; stereoselectivity
• Markovnikov addition of HX
• peroxide effect; anti-Markovnikov
• addition of H2SO4 to alkenes; hydration
• Hydroboration-Oxidation
• Halogenation; vicinal halohydrins
• Rates of addition to alkenes
221-15-Jun8.pdf
Lecture 16: June 9, 2016
Main topics include:
• Alkynes: physical/chemical properties
• alkyne acidity; common bases
• alkylation of alkynes with alkyl halides
• double dehydrohalogenation
• addition reactions: HX, Hg2+ hydration, halogenation, enol tautomerization
• hydroboration-oxidation = aldehyde
• hydrogenation; Lindlar catalyst (cis)
• dissolving metal reduction (trans)
221-16-Jun9.pdf
Lecture 17: June 14, 2016
Main topics include:
• review of allylic substitution runs
• kinetic vs thermodynamic addition
• Diels-Alder Reaction; stereospecificity
• Diels-Alder activating groups
• Frontier molecular orbitals (FMOs)
• Constructing the HOMO and LUMO of conjugated systems
• Benzene: observations of aromaticity
• Constructing MOs of benzene
221-17-Jun14.pdf
Lecture 18: June 15, 2016
Main topics include:
• MO diagrams; Frost circle
• Consequences of aromaticity: tropylium
• Reactions at benzylic carbons
• Clemensen and Wolf-Kishner reduction
• KMnO4 oxidation of benzylic carbons
• Electrophilic aromatic substitution
• arenium ions
• nitration, sulfonation, bromination
• Friedel-Crafts alkylation and acylation
223-18-Jun18.pdf
Lecture 19: June 16, 2016
Main topics include:
• rate of SE-Ar with EDGs and EWGs
• ortho/para, meta directors
• multiple substituent effects
• synthesis of aromatic compounds
221-19-Jun16.pdf
Lecture 20: June 20, 2016
Main topics include:
• nucleophilic aromatic substitution
• addition/elimination mechanism
• benzyne intermediates
• protein labels
221-20-Jun20.pdf