Organic Chemistry: How to Build People

Explore how functional groups determine properties and acid-base sites in organic molecules, and analyze electron distributions, bond and molecular dipole moments, and lone-pair effects on reactivity.

Explore intermolecular forces that govern solids and liquids, including dipole-dipole, London dispersion, and hydrogen bonds, and show how these forces influence boiling points and solubilities.

Apply the like dissolves like rule to polar and nonpolar solutes and solvents. Explore polar solutes in polar solvents and nonpolar solutes in nonpolar solvents with hydration and entropy.

Explore Arrhenius, Brønsted–Lowry, and Lewis definitions of acids and bases, and how pH and hydronium–hydroxide balance define aqueous acidity.

Explore Brønsted–Lowry acids and bases through proton transfer, where acids donate protons and bases accept them, linking to Arrhenius definitions and conjugate acid–base pairs like NH4+ and NH3.

Learn how acid strength is quantified by Ka and pKa, how base strength relates to conjugate bases through Kb and Kw, and why reactions favor the weaker acid and base.

Explore how Brønsted–Lowry acid–base reactions favor the weaker acid and base, using pKa and pKb to predict equilibrium for acetic, propionic acids, water, phenol, and aniline.

Explore how water, as an amphoteric solvent, levels acidity and basicity by forming H3O+ and OH−, with pKa and pKb ranges defined in water.

Explore how electronegativity and size influence acidity by analyzing conjugate base stability and Brønsted–Lowry acids. Observe pKa trends across the periodic table as size increases downward and electronegativity increases.

Examine inductive effects that stabilize the conjugate base via sigma bonds, increasing acid strength; fluorine and chlorine near the acidic site elevate acidity, with more halogens amplifying the effect.

Explain how hybridization controls acidity by stabilizing the nonbonding lone pair in conjugate bases, with increasing s-character from sp3 to sp, as demonstrated in nitrogen and carbon compounds.

Explore resonance stabilization of conjugate bases, where delocalized charge boosts acidity. Compare amides and amines to see carbonyl resonance lowers basicity, and how cyano and nitro groups stabilize conjugate bases.

Explore Lewis acids and bases, redefining Brønsted–Lowry and Lewis acid–base chemistry with lone-pair donation and electron-pair acceptance beyond proton transfer, using curved arrows to show nucleophiles and electrophiles.

Explore the curved-arrow formalism to depict electron flow in organic reactions, showing lone pairs moving from donors to acceptors and bonds forming or breaking, including resonance considerations.

Explore hydrocarbon classes—alkanes, alkenes, alkynes, and aromatic hydrocarbons—and learn how functional groups, nomenclature, and alkyl and aryl substituents shape structure and reactivity.

Explore the major oxygen-containing functional groups—alcohols, ethers, aldehydes, ketones, carboxylic acids, and acid derivatives—and how their polarity and hydrogen bonding influence solubility and naming.

Explore nitrogenous functional groups such as amines, amides, and nitriles, and how basicity and hydrogen bonding affect solubility. Note amides form strong hydrogen bonds and exhibit high boiling points.

Explore alkanes, the saturated hydrocarbon backbone with only single bonds and sp3 carbons, lacking functional groups and heteroatoms, and learn their naming and role in hydrocarbon classification.

Explore molecular formulas of first 20 unbranched alkanes, showing isomers share the same formula and that CnH2n+2 applies to both straight-chain and branched alkanes, increasing by two hydrogens per carbon.

Learn how IUPAC names alkanes by selecting the longest carbon chain, numbering to minimize substituent locants, and naming alkyl substituents such as methyl, ethyl, propyl, isopropyl, and tert-butyl, halogen substituents.

Explore how alkanes' solubility, density, boiling points, and melting points change with molecular weight and branching, and why even and odd carbon counts influence packing and phase behavior.

Discover how petroleum distillation yields alkane fractions for fuels like methane, propane, gasoline, kerosene, and diesel, and how cracking and hydrocracking refine crude oil.

Explore why alkanes are the least reactive organic compounds, often requiring high temperatures. Examine combustion, cracking, hydrocracking, and halogenation forming alkyl halides, noting lab limits and industry relevance.

Explore the structure and conformations of alkanes, from methane to ethane rotation, using Newman projections and dihedral angles to compare eclipsed and staggered conformations and torsional strain.

Examine how butane rotates around the central C2–C3 bond, contrasting anti, gauche, and eclipsed conformations and their torsional energies, with steric strain shaping alkane stability.

Higher alkanes favor anti and gauche conformations about carbon–carbon bonds; room-temperature rotation yields gauche kinks in the zigzag chain and influences lipid melting points and nutrition.

Explore how cycloalkanes, rings of CH2 groups, illustrate the properties and stability of cyclic compounds. Identify the general formula CnH2n, line-angle formulas, and naming and numbering rules.

Explore cis-trans isomerism in cycloalkanes by comparing it with but-2-ene and 1,2-dimethylcyclopentane; learn how cycloalkanes have two faces and how cis and trans configurations cannot interconvert without breaking bonds.

Explore the stabilities and conformations of cycloalkanes, revealing how ring size drives angle and torsional strain; cyclohexane shows no strain, while cyclopropane and cyclobutane are highly strained.

Explore cyclohexane conformations in detail, including chair and boat forms, axial and equatorial positions, energy barriers, and how interconversion and substitutions govern stability and reactivity.

Explore how methylcyclohexane's chair conformations favor equatorial over axial positions, with ring-flips, and 1,3-diaxial interactions accounting for a 7.6 kJ/mol stability difference.

Explore conformations of disubstituted cyclohexanes, comparing diaxial and diequatorial forms, cis and trans isomers, and how bulky groups like tert-butyl favor equatorial positions, even in twist-boat forms.

Examine how two rings form bicyclic systems through fused, bridged, and spiro connections. Learn bicyclo nomenclature, role of bridge counts in naming, and chair conformations of cis- and trans-decalin.

Explore the study of chemical reactions by examining bond making and breaking, reaction mechanisms, intermediates, and the thermodynamics and kinetics that govern halogenation of alkanes.

Explore the chlorination of methane, where light or heat initiates a multi-step mechanism, producing chlorinated products; examine thermodynamics, kinetics, and high quantum yield to explain product distribution.