EE-Learning
Regioselectivity, stereoselectivity, and stereospecificity
Catogry:
Science & Engineering
Subject:
Chemistry
Course:
Organic Chemistry
Lecture List
Correction - 2-propylheptane should never be the name!
Proton NMR practice 3
Proton NMR practice 2
Proton NMR practice 1
Hydrogen deficiency index
Complex splitting
Coupling constant
Multiplicity: n + 1 rule
Spin-spin splitting (coupling)
Integration
Diamagnetic anisotropy
Electronegativity and chemical shift
Chemical shift
Chemical equivalence
Nuclear shielding
Introduction to proton NMR
Conjugation and color
Absorption in the visible region
UV/Vis spectroscopy
IR spectra practice
IR signals for carbonyl compounds
Symmetric and asymmetric stretching
Signal characteristics - shape
Signal characteristics - intensity
IR spectra for hydrocarbons
Signal characteristics - wavenumber
Bonds as springs
Introduction to infrared spectroscopy
Amine naming 2
Amine naming introduction
Intramolecular aldol condensation
Retro-aldol and retrosynthesis
Mixed (crossed) aldol condensation using a lithium enolate
Mixed (crossed) aldol condensation
Aldol condensation
Aldol reaction
Kinetic and thermodynamic enolates
Enolate formation from ketones
Enolate formation from aldehydes
Keto-enol tautomerization (by Jay)
Keto-enol tautomerization (by Sal)
Beta-lactam antibiotics
Acid and base-catalyzed hydrolysis of amides
Acid-catalyzed ester hydrolysis
Nucleophilic acyl substitution
Reactivity of carboxylic acid derivatives
Nomenclature and properties of amides
Nomenclature and properties of esters
Nomenclature and properties of acyl (acid) halides and acid anhydrides
Decarboxylation
Preparation of amides using DCC
Preparation of esters via Fischer esterification
Preparation of acid anhydrides
Preparation of acyl (acid) chlorides
Reduction of carboxylic acids
Carboxylic acid nomenclature and properties
Amide formation from acyl chloride
Relative stability of amides, esters, anhydrides, and acyl chlorides
Amides, anhydrides, esters, and acyl chlorides
Acid chloride formation
Fischer esterification
Carboxylic acid naming
Carboxylic acid introduction
Oxidation of aldehydes using Tollens' reagent
Formation of alcohols using hydride reducing agents
Addition of carbon nucleophiles to aldehydes and ketones
Formation of oximes and hydrazones
Formation of imines and enamines
Acetals as protecting groups and thioacetals
Formation of acetals
Acid and base catalyzed formation of hydrates and hemiacetals
Formation of hemiacetals and hemiketals
Formation of hydrates
Reactivity of aldehydes and ketones
Physical properties of aldehydes and ketones
Nomenclature of aldehydes and ketones
Ketone naming
Aldehyde introduction
Nucleophilic aromatic substitution II
Nucleophilic aromatic substitution I
Synthesis of substituted benzene rings II
Synthesis of substituted benzene rings I
Reactions at the benzylic position
Birch reduction II
Birch reduction I
Multiple substituents
Meta directors II
Meta directors I
Ortho-para directors III
Ortho-para directors II
Ortho-para directors I
Friedel-Crafts acylation
Friedel-Crafts alkylation
Sulfonation
Nitration
Halogenation
Electrophilic aromatic substitution mechanism
Aromatic heterocycles II
Aromatic heterocycles I
Aromatic stability V
Aromatic stability IV
Aromatic stability III
Aromatic stability II
Aromatic stability I
Friedel crafts acylation addendum
Friedel-Crafts acylation
Bromination of benzene
Electrophilic aromatic substitution
Naming benzene derivatives
Naming benzene derivatives introduction
Diels-Alder: regiochemistry
Diels-Alder: intramolecular
Diels-Alder: endo rule
Diels-Alder: stereochemistry of diene
Diels-Alder: stereochemistry of dienophile
Diels-Alder reaction
Preparation of sulfides
Ring opening reactions of epoxides: Acid-catalyzed
Ring-opening reactions of epoxides: Strong nucleophiles
Preparation of epoxides: Stereochemistry
Nomenclature and preparation of epoxides
Cyclic ethers and epoxide naming
Acidic cleavage of ethers
Williamson ether synthesis
Properties of ethers and crown ethers
Ether nomenclature
Ether naming and introduction
Preparation of alkyl halides from alcohols
Formation of nitrate esters
SN1 and SN2 reactions of alcohols
Preparation of mesylates and tosylates
Protection of alcohols
Biological redox reactions
Oxidation of alcohols II: Examples
Oxidation of alcohols I: Mechanism and oxidation states
Synthesis of alcohols using Grignard reagents II
Synthesis of alcohols using Grignard reagents I
Preparation of alcohols using LiAlH4
Preparation of alcohols using NaBH4
Physical properties of alcohols and preparation of alkoxides
Alcohol nomenclature
Alcohol properties
Triple bonds cause linear configurations
Alcohols
Synthesis using alkynes
Halogenation and ozonolysis of alkynes
Hydroboration-oxidation of alkynes
Hydration of alkynes
Hydrohalogenation of alkynes
Reduction of alkynes
Preparation of alkynes
Alkyne acidity and alkylation
Alkyne nomenclature
Ozonolysis
Syn dihydroxylation
Epoxide formation and anti dihydroxylation
Halohydrin formation
Halogenation
Hydroboration-oxidation: Mechanism
Hydroboration-oxidation
Hydration
Hydrohalogenation
Hydrogenation
Alkene stability
E-Z system
Cis-trans isomerism
Alkene nomenclature
Alkene structure and classification
Polymerization of alkenes with acid
Addition of water (acid-catalyzed) mechanism
Markovnikov's rule and carbocations
Introduction to reaction mechanisms
Entgegen-Zusammen naming scheme for alkenes examples
cis-trans and E-Z naming scheme for alkenes
Naming alkenes examples
Elimination vs substitution: tertiary substrate
Elimination vs substitution: secondary substrate
Elimination vs substitution: primary substrate
Elimination vs substitution: reagent
Regioselectivity, stereoselectivity, and stereospecificity
E2 elimination: Substituted cyclohexanes
E2 elimination: Stereospecificity
E2 elimination: Stereoselectivity
E2 mechanism: regioselectivity
E2 mechanism: kinetics and substrate
E1 mechanism: carbocations and rearrangements
E1 mechanism: stereoselectivity
E1 elimination: regioselectivity
E1 mechanism: kinetics and substrate
Sn1 vs Sn2: Summary
Sn1 vs Sn2: Solvent effects
Sn1 and Sn2: leaving group
Sn2 mechanism: stereospecificity
Sn2 mechanism: kinetics and substrate
Sn1 carbocation rearrangement (advanced)
Sn1 mechanism: carbocation rearrangement
Carbocation rearrangement practice
Carbocation stability and rearrangement introduction
Sn1 mechanism: stereochemistry
Sn1 mechanism: kinetics and substrate
Alkyl halide nomenclature and classification
Intro to organic mechanisms
Curly arrow conventions in organic chemistry
Identifying nucleophilic and electrophilic centers
E2 E1 Sn2 Sn1 reactions example 3
E2 E1 Sn2 Sn1 reactions example 2
Comparing E2, E1, Sn2, Sn1 reactions
Zaitsev's rule
E1 reactions
E2 reactions
Nucleophilicity vs. basicity
Nucleophilicity (nucleophile strength)
Free radical reactions
Meso compounds
Enantiomers and diastereomers
Stereoisomers, enantiomers, diastereomers, constitutional isomers and meso compounds
Optical activity calculations
Optical activity
Fischer projection practice
Fischer projection introduction
More R,S practice
R,S system practice
R,S (Cahn-Ingold-Prelog) naming system example 2
R,S system
Cahn-Ingold-Prelog system for naming enantiomers
Drawing enantiomers
Identifying chirality centers
Stereoisomers, enantiomers, and chirality centers
Chiral vs achiral
Chiral examples 2
Chiral examples 1
Introduction to chirality
Identifying functional groups
More functional groups
Functional groups
Polysubstituted cyclohexane
Disubstituted cyclohexane
Monosubstituted cyclohexane
Drawing chair conformations
Conformations of cyclohexane
Stability of cycloalkanes
Double Newman diagram for methylcyclohexane
Chair and boat shapes for cyclohexane
Newman projection practice 2
Newman projection practice 1
Conformational analysis of propane
Conformational analysis of ethane
Conformations of ethane
Newman projections 2
Newman projections
Heats of combustion of alkanes
Naming cubane
Bicyclic compounds
Alkane and cycloalkane nomenclature III
Alkane and cycloalkane nomenclature II
Alkane and cycloalkane nomenclature I
Organic chemistry naming examples 4
Naming two isobutyl groups systematically
Naming a cycloalkane
Organic chemistry naming examples 3
Organic chemistry naming examples 2
Alkane with isopropyl group
Naming alkanes with ethyl groups
Common and systematic naming: iso-, sec-, and tert- prefixes
Correction - 2-propylheptane should never be the name!
Naming alkanes with alkyl groups
Naming simple alkanes
Representing structures of organic molecules
Stabilization of a conjugate base: solvation
Stabilization of a conjugate base: hybridization
Stabilization of a conjugate base: induction
Stabilization of a conjugate base: resonance
Acid strength, anion size, and bond energy
Stabilization of a conjugate base: electronegativity
Using pKa values to predict the position of equilibrium
Using a pKa table
Ka and pKa review
Ka and acid strength
Organic acid-base mechanisms
Acid-base definitions
Resonance structures and hybridization
Common mistakes when drawing resonance structures
Resonance structures for benzene and the phenoxide anion
Resonance structure patterns
Resonance structures
Organic oxidation-reduction reactions
Oxidation states of carbon
Formal charge on oxygen
Formal charge on nitrogen
Formal charge on carbon
Comparing formal charges to oxidation states
Solubility of organic compounds
Boiling points of organic compounds
Intermolecular forces
Dipole moment
Electronegativity and bonding
Structural (constitutional) isomers
Three-dimensional bond-line structures
Bond-line structures
Condensed structures
Tetrahedral bond angle proof
Organic hybridization practice
Sp hybridization
sp² hybridization
Steric number and sp3 hybridization
sp³ hybridization
Pi bonds and sp2 hybridized orbitals
sp3 hybridized orbitals and sigma bonds
Dot structures II: Multiple bonds
Dot structures I: Single bonds