Organic Chemistry Online Course 15+hours lectures & examples

Explore the history of organic chemistry, from its 18th-century roots to the separation from inorganic chemistry, and learn how urea's synthesis, carbon’s four-valence, and structure theory shaped modern concepts.

The carbon atom holds a privileged position in the periodic table, driving its tendency to form carbon–carbon bonds and four covalent bonds, underpinning carbon-based life and organic chemistry.

Explore the hybrid states of carbon, including tetrahedral and trigonal planar geometries, three or four sigma bonds, and the formation of pi bonds in double bonds.

Explore how electronegativity and electron affinity govern chemical bonding in organic compounds, distinguishing ionic, polar covalent, and nonpolar covalent bonds using the Pauling scale.

Explore homonuclear bonding and the carbon-carbon single bond through molecular orbitals, bonding and antibonding orbitals, and sigma bonds formed by sp3 hybrid overlap.

Explore carbon–carbon double and triple bonds by detailing sigma and pi bonds, sp2 hybridization, and planar molecular geometry arising from orbital overlap and bond angles near 128 degrees.

Explore heteronuclear bondings and electronic effects by examining polarized bonds, electron negativity, and the inductive effect—both minus and plus—how electron density shifts influence reaction mechanisms.

Explore how mesomeric effects shift electron density in conjugated systems and influence resonance in benzene, including donor and withdrawal groups.

Learn how intermolecular bonding, especially hydrogen bonds between hydrogen and electronegative atoms, shapes organic structure, DNA base pairing, protein folding, and water's solvent properties that affect boiling points.

Explore intermolecular forces, including orientation (dipole-dipole) interactions, induction effects, and London dispersion forces, explained as quantum-mechanical fluctuations of electron clouds that create temporary dipoles and attractions.

Explore functional groups and their role in organic chemistry by learning how classification tests distinguish compounds, predict reactivity, and organize molecules by shared properties.

Explore how quantum mechanics describes electrons with wave functions and orbitals, and how orbital overlap creates bonding molecular orbitals that stabilize covalent bonds.

Explore bonding schemes, from ionic transfer to reach noble gas octet configurations, to covalent sharing, sigma bonds, and orbital hybridization shaping molecular geometry.

Examine antibonding orbitals and how overlapping atomic orbitals form bonding and antibonding molecular orbitals, with bonding lower in energy and antibonding higher, and how excitation promotes electrons to energy levels.

Explore resonance as the delocalization of electrons across molecules, creating resonance hybrids from multiple contributing structures like benzene, with equal bond lengths and stability from added resonance energy.

Explore how conjugated π systems form from overlap of atomic orbitals into bonding and anti-bonding molecular orbitals, with energy-symmetric distributions and electron filling yielding stable molecules.

Explore aromaticity through molecular orbitals in cyclic conjugated systems, highlighting benzene’s six pi electrons filling bonding orbitals for stability, equal bond lengths, and anti-aromatic contrasts per Huckel's rule.

Compute carbon oxidation numbers and classify functional groups by oxidation state, then match reagents’ oxidizing or reducing properties to enable compatible organic transformations.

Explore oxidation states in organic chemistry by applying carbon oxidation number rules: bonds to electronegative elements add, bonds to electropositive elements subtract, and multiple bonds count as multiple contributions.

Learn how to track carbon oxidation states in reactions, including internal redox and hydrogenation, and distinguish oxidizing and reducing agents in methane combustion and alcohol oxidation.

Explore Bronsted–Lowry and Lewis acid–base theories, including proton transfer, conjugate pairs, and how acids or bases act only in the context of the reaction, with examples in organic chemistry.

Explore how acid and base strength is measured by ionization in water, comparing strong and weak acids and bases, conjugate bases and acids, and ionization constants.

Explore acid-base equilibria by learning how to use the equilibrium constant and pKa values to predict the dominant side of a reaction, with practical lab applications.

Investigate how inductive and mesomeric effects, hybridization, and electronic activity govern the acidity of organic acids and the stability of their conjugate bases.

Explore the factors that govern the basicity of organic bases, including inductive effects, hybridization, and lone-pair availability, and how substituents influence reactivity.

Explore how electron movement drives organic reactions, using curved-arrow notation to track bond formation and lone-pair donation between Lewis acids and bases.

Explore heterolytic bond cleavages and formation in organic reactions, detailing how lone pairs and formal charges drive bond making and breaking through donor–acceptor interactions.

Explore homolytic bond making and breaking, driven by single-electron processes that form radical species and enable bond formation or cleavage in organic transformations.

Depicts how organic reaction mechanisms are illustrated, showing bond formation and breaking, substitution, electron movement, resonance, and the energy changes that drive outcomes.

Explore how organic reaction mechanisms unfold through stepwise transformations, energy barriers, and activated complexes, showing how reactants convert to products, reaction rates, and how conditions shape outcomes.

Explore reaction energetics by examining activation energy, energy barriers, and the transition state that governs how reactants convert to products, with free energy changes and rate implications.

Examine how the activated complex and transition state relate structure to energy, showing how reactants surmount energy barriers to form products.

Apply the Hammond postulate to connect transition state energy with reactant structure, and examine how structural changes influence activation barriers and reaction rates.

Explore reaction kinetics in organic chemistry, analyzing how concentration affects rate, distinguishing first-order and second-order processes, and applying integrated rate equations and rate constants to predict concentration changes over time.

Explore isotope effects in organic reactions, comparing primary and secondary kinetic isotope effects, zero-point energy, and how isotopic substitution shifts transition states and reaction rates.

Explore how electronic effects influence reaction rates by examining charge development in transition states and inductive effects.

Explore the Hammett equation as a quantitative tool to monitor charge distribution in substituted benzene rings, using reaction constants and substituent effects to describe rate changes.

Explore stereochemistry and the role of functional groups in shaping molecular properties, including optical isomers (enantiomers), geometric isomers, and the distinction between configuration and conformation.

Examine optical isomers, mirror-image molecules that cannot be superimposed, and understand enantiomers and chirality. See how optical activity rotates polarized light from tetrahedral stereocenters forming left- and right-handed forms.

Explore stereochemical structures, including Fischer projections and wedge-and-dash notation, to visualize three-dimensional spatial arrangements in organic molecules.

Learn to assign R or S configurations for chiral centers using CIP priority rules based on atomic numbers, orient the center, and follow the sequence clockwise or counterclockwise.

Explore how multiple stereocenters generate several stereoisomers, determined by R and S configurations, including enantiomers and diastereomers, with internal mirror planes producing meso forms.

Explore optical activity of chiral molecules, including rotation of plane polarized light, specific rotation, enantiomers, and optical purity under varying concentration, path length, and wavelength.

Explore how enantiomers exhibit distinct solid-state properties, including melting points and stability, and how crystallization creates conglomerates, racemic compounds, or enantiomerically enriched mixtures.

Explore methods to resolve enantiomers, including crystallization with optically active acids to form diastereomers, conversion to esters of optically active acids, and chromatography- and enzyme-based resolutions.

Investigate how enantiomers form at tetrahedral chiral centers, distinguish mirror-image pairs by R and S configuration and optical rotation, and explore how additions create either enantiomer.

Explore how diastereomers form when multiple chiral centers arise, producing non-mirror stereoisomers and diastereomeric pairs with stereospecific and stereoselective outcomes.

Explore the conformations of cyclic hydrocarbons, highlighting cyclohexane chair conformation as the most stable, strain-free form, and the role of axial and equatorial hydrogens and ring flips.

Examine conformations of substituted cyclohexanes, comparing axial and equatorial positions and chair flips, and show how 1,3-diaxial interactions favor equatorial substitutions.

Explore the definitions of nucleophiles and electrophiles, identify electron-rich and electron-deficient centers, and understand how these concepts drive organic reactions.

Explore how electronegativity and lone pairs define nucleophiles and electrophiles in organic chemistry. Compare fluoride, oxygen, and nitrogen to predict reactivity in water, ammonia, and hydrogen fluoride.

Identify and understand functional groups as the drivers of organic reactions, recognize common groups and their properties to predict reactivity and guide bond formation.

Explore acid-base reactions, functional group transformations, and carbon–carbon bond formation as key categories guiding synthetic organic chemistry, using mechanism and curved arrows to predict outcomes.

Explore the properties of alkanes, the simplest hydrocarbons with single bonds, including straight, branched, and cycloalkanes; they are non-polar, water-insoluble solvents, and primarily undergo substitution or combustion.

Discover the properties of alkenes and alkynes: carbon–carbon double and triple bonds, sp2 and sp hybrids, and E/Z isomerism, plus their nonpolar nature and reactivity.

Learn how electrophilic addition to symmetrical alkenes proceeds with hydrogen halides like HBr, forming a carbocation intermediate and adding the halogen across the double bond.

Study electrophilic addition to symmetrical and unsymmetrical alkenes via carbocation mechanisms. Learn that hydrogen adds to the more hydrogen-rich carbon and halogen to the more substituted carbon; water forms halohydrins.

Explore how carbocations are stabilized by inductive effects from neighboring groups, by hyperconjugation with adjacent C-H and C-C bonds, and by sharing positive charge with nearby atoms such as halogens.

Examine catalytic hydrogenation of alkenes with metal catalysts like palladium to add hydrogen under conditions, and oxidation routes such as ozonolysis and permanganate or osmium tetroxide yielding carbonyls and acids.

Explore hydroboration of alkenes, adding boron to the less substituted carbon and converting it to alcohol via oxidation with hydrogen peroxide, yielding anti-Markovnikov, stereospecific alcohols.

Learn hydroboration of alkenes and related electrophilic additions, outlining the reaction steps and regioselectivity, and compare Markovnikov-type outcomes in hydrogen halide additions.

Learn how catalytic hydrogenation reduces alkynes to alkenes and alkanes, and how deprotonated terminal alkynes undergo alkylation with alkyl halides to form new carbon–carbon bonds.

Explore conjugated dienes and how resonance and hybridization affect bond lengths. Learn how the Diels-Alder reaction, a concerted cycloaddition, forms six-membered rings without intermediates.

Explore aromatic chemistry focusing on benzene stability, delocalized pi electrons, and Huckel's 4n+2 rule. Learn how cyclic, planar, sp2-hybridized rings drive distinctive reactions in aromatic compounds.

Explains electrophilic substitutions of benzene, focusing on bromination and chlorination, the formation of arenium ion intermediates, resonance stabilization, and the role of Lewis acids in activating halogens for substitution.

Explore electrophilic substitutions on benzene, including Friedel-Crafts alkylation and acylation with Lewis acids such as aluminum chloride, and the role of carbocation intermediates and rearrangements. Compare nitration mechanisms.

Learn how to synthesize mono-substituted benzenes by planning with retro-synthesis, introducing indirect functional groups that can be converted to the desired substituent, and performing multi-step transformations.

Examine how substituents on an aromatic ring direct electrophilic substitution to ortho, meta, and para positions, via inductive and resonance effects, and classify activating groups into four directing types.

Explore how activating and deactivating groups guide electrophilic substitutions on mono-substituted aromatic rings, with resonance donation and inductive effects stabilizing arenium intermediates to favor ortho and para positions.

Learn how to synthesize di- and tri-substituted benzenes by using directing properties of substituents and removable blocking groups to steer ortho, meta, and para substitutions.

Explore how aromatic rings resist oxidation while side chains oxidize to carboxylic acids, and how selective reduction can modify substituents without changing the ring under strong conditions.

Explore aldehydes and ketones, their carbonyl polarity, boiling points, and water solubility, plus acid-base catalyzed tautomerism and preparation routes from primary alcohols, esters, and chlorides.

Explore nucleophilic addition to aldehydes and ketones using charged nucleophiles, with Grignard-type reagents providing carbon nucleophiles that form carbon-carbon bonds and yield primary, secondary, and tertiary alcohols after workup.

Explore nucleophilic addition with charged nucleophiles. Reduce aldehydes and ketones to primary and secondary alcohols using hydride donors like sodium borohydride and lithium aluminum hydride, and form cyanohydrins with cyanide.

Explore how electronic inductive effects and steric factors determine the reactivity of aldehydes and ketones in nucleophilic addition, highlighting transition-state stability and product outcomes.

Investigate how nitrogen nucleophiles attack carbonyl groups, form intermediates via proton transfers, with water acting as a catalyst; explore primary and secondary amines and a biological amino acid synthesis example.

Explain acid-catalyzed nucleophilic addition of alcohols to carbonyls to form hemiacetals and acetals, with water-driven hydrolysis reversing the process, and discuss protecting aldehydes and ketones with cyclic and thioacetals.

Explore the reactions of enolate ions, including alkylation and aldol reactions, and compare O- and C- attack pathways to form carbon–carbon bonds.

Enolate ions react with alkyl halides to form carbon-carbon bonds and can self-condense under base to give beta-hydroxy products. Dehydration and cross aldol (claisen-schmidt) reactions then produce extended conjugated systems.

Master alpha halogenation of carbonyl compounds by enolate formation, with base-driven deprotonation, non-radical halogenation, and the iodoform test's yellow precipitate confirming multiple halogenations.

The lecture covers the reduction of aldehydes and ketones to primary and secondary alcohols using various methods and conditions, and the oxidation of aldehydes to carboxylic acids with silver oxide.

Explore α,β-unsaturated aldehydes and ketones, their conjugation with the carbonyl, and conjugate additions at the beta position. Learn reduction with sodium borohydride to allylic alcohols under controlled conditions.

Explore carboxylic acids and their derivatives, focusing on the polar carbonyl group, hydrogen bonding, high boiling points, and water solubility via nucleophilic substitution.

Explore nucleophilic substitution of carboxylic acids and derivatives, detailing mechanisms with acid chlorides, leaving group stability of chloride, and how carbonyl compounds enable substitution.

Outline reactivity of carboxylic acids and derivatives, showing acid chlorides as most reactive for nucleophilic substitution, with esters and amides less reactive; electronic and steric factors drive the trends.

Explore how to prepare carboxylic acids by oxidizing primary alcohols and aldehydes, hydrolyzing esters, oxidizing aromatics to benzoic acids, and forming acids from alkyl halides via cyanide or CO2 pathways.

Explore the main reactions of carboxylic acids and derivatives, including base reactions forming carboxylate salts, hydrolysis of esters and acid chlorides, and nuclear substitution to convert esters.

Explore the reactions of carboxylic acids and derivatives, including Friedel-Crafts acylation of arenes with acid chlorides and Grignard-based formation of tertiary alcohols, plus reductions to primary alcohols.

Learn how enolates form by deprotonating acidic alpha protons with strong bulky bases, then undergo alkylation and Claisen condensations, including cross- and self-condensation control.

Explore preparation of carboxylic acid derivatives, including acyl chlorides from carboxylic acids with thionyl chloride. Learn esters by alcoholysis and anhydrides by heating, with mechanism highlights.

Explore alkyl halides, where an alkyl group bonds to a halogen, and how primary and secondary alcohols convert to them via hydrogen halides.

Explore nucleophilic substitution of alkyl halides, comparing SN1 and SN2 mechanisms, transition states, and how leaving groups, nucleophiles, and primary, secondary, and tertiary halides influence reactivity and stereochemistry.

SN1 substitution of alkyl halides proceeds via carbocation formation followed by nucleophile attack from either side. Rate is first order in the alkyl halide and racemization occurs for chiral substrates.

Compare sn1 and sn2 substitution, noting primary halides favor sn2 while tertiary favor sn1; protic solvents like water or alcohol influence rate; leaving group quality and nucleophile strength matter.

Analyze how electronic and steric factors influence SN1 and SN2 reactions, compare primary, secondary, and tertiary alkyl halides, and explain mechanism determination through rate and intermediates.

Explore elimination of alkyl halides via e2 and e1 mechanisms, driven by beta protons and base strength. Learn how solvent and substrate type influence rate, product geometry, and sn1 competition.

Compare elimination and substitution of primary, secondary, and tertiary alkyl halides across SN1, SN2, E1, and E2 mechanisms, showing how base strength, solvent, and temperature drive product selectivity.

Explore the reactions of alkyl halides, including cyanide substitution and elimination to form substituted products, and magnesium-mediated reactions that yield carboxylic acids via carbon dioxide.

Explore alcohols and phenols, focusing on the hydroxyl group, hydrogen bonding–driven boiling points and solubility, and the distinct acid–base behavior of phenols versus alcohols.

Explore how alcohols react via substitution, dehydration, and carbon–carbon forming reactions, using Grignard or organolithium reagents and activation by phosphorus oxychloride under acid or base conditions.

Analyze alcohol reactions, including acid-catalyzed hydration and E2 dehydration, with secondary alcohols favored, and SN2 formation of alkyl halides using phosphorus tribromide.

Explore phenol reactions, focusing on acidity, electrophilic substitution directing to ortho and para, and conversions to ethers under mild base conditions, with notes on group effects and ester hydrolysis limitations.

Explore amines in organic chemistry, detailing primary, secondary, and tertiary structures, lone pair hybridization, pyramidal geometry, inversion, basicity trends, hydrogen bonding, and reactivity with acids, bases, and electrophiles.

Learn amine preparation via Gabriel synthesis, reductive amination, and alkyl halide substitution, plus Hofmann and Curtius rearrangements for primary to tertiary amines.

Explore how amines react with alkyl halides to form primary, secondary, and tertiary amines and quaternary ammonium salts, including reductive amination and Hofmann elimination.

Explore the reactions of amines with aryl halides, Hofmann elimination of quaternary ammonium salts, and diazonium formation for electrophilic aromatic substitution and dye coupling.

Explore visible and ultraviolet spectroscopy as a key tool for analyzing organic compounds. Relate energy to electronic transitions from HOMO to LUMO in conjugated systems and measure lambda max.

Explore infrared spectroscopy by analyzing stretching and bending vibrations, which depend on bond stiffness and atom masses, and use the fingerprint region for identifying functional groups via dipole moment changes.

Explore the basics of proton NMR spectroscopy, including how external magnetic fields split proton orientations, precession at the Larmor frequency, and shielding that yields distinct signals revealing proton environments.

Explore proton NMR spectroscopy concepts: chemical shifts in ppm with internal references, shielding and inductive effects, and spin-spin coupling producing multiplets across up to three bonds.