Organic Chemistry I Crash Course - OChem Made Simple

Explore sp3, sp2, and sp hybridizations and how carbon forms four single bonds in alkanes, like methane and ethane, through hybridized orbitals, yielding sigma bonds and 109.5° tetrahedral geometry.

Explore sp2 hybridization in alkenes, forming three sigma bonds from hybrid orbitals. Learn how unhybridized p orbitals create the pi bond, yielding trigonal planar geometry and restricted rotation.

Explore sp hybridization in carbon, forming two sp orbitals for sigma bonds and two unhybridized p orbitals for pi bonds above, below, and out of the page.

Count electron groups around atoms to identify hybridization quickly, using the octet rule and the sp, sp2, sp3 framework. Visualize bond angles and shapes with Vsepr rather than orbital diagrams.

Explore formal charge in carbon, compare it to the octet rule, and learn how bonds and lone pairs determine charge, including trading bonds for lone pairs to form carbocations.

Explore nitrogen's formal charges across sp3, sp2, and sp hybrids in neutral, negative, and positive states by counting bonds and lone pairs to satisfy five valence electrons.

Explore the formal charges of oxygen across neutral, negative, and positive forms in sp3, sp2, and sp hybridization, using lone pairs and bonds to explain hydroxide and carbonyl behavior.

Identify the longest carbon chain as the parent, name alkanes from methane to decane, and name branches like methyl, ethyl, and propyl using proper numbering, dash, comma, and alphabetical order.

Explain naming of complex alkane branches, using iso prefixes and isopropyl, sec- and tert-butyl, with longest chain and alphabetical ordering. Note sp2 and sp carbons for alkenes and alkynes.

Learn to name alkenes and alkynes, apply cis/trans isomerism, and use priority-based numbering to place double and triple bonds, including situations with multiple bonds in a chain.

Learn to name simple alcohols and ethers, prioritizing the hydroxyl group for numbering, using common names like isopropyl alcohol and tert-butyl alcohol, and apply dialkyl ether naming with alphabetical order.

Master naming rings and bicyclic rings using the cyclo prefix, numbering to minimize branch numbers, and bicyclo nomenclature with square brackets for fused and bridged systems.

Explain resonance as the blending of forms into a hybrid, using two-headed arrows and moving only lone pairs and pi bonds without breaking single bonds, to stabilize charged species.

Explore resonance for positively charged molecules, including allylic and benzylic cases, using bond-to-bond arrows and delocalization to stabilize carbocations and form resonance hybrids.

Explore how negative charges stabilize through resonance by using atom-to-bond and bond-to-atom arrows, showing electron pushing and delocalization in allylic and benzylic cases.

Explore resonance for oxygen and nitrogen by moving lone pairs with bond-to-atom arrows. Examine major and minor forms and neutral versus charged states in esters and amides.

Compare major and minor resonance forms, rank them by octet rule violations and separation of charge, and show how major forms dominate the resonance hybrid.

Explore constitutional isomerism, where molecules share the same molecular formula but differ in connectivity, producing different names and properties.

Learn to use degrees of unsaturation as an accounting for hydrogens to count pi bonds and rings, enabling quick drawing of constitutional isomers for hydrocarbons and oxygen/nitrogen-containing molecules.

Explore Newman projections as a tool to visualize rotational isomers around sp3 carbon bonds, compare staggered and eclipsed ethane conformations, and introduce dihedral angle and torsional strain.

Explore torsional strain from eclipsing bonds and steric strain from spatial clashes in Newman projections of butane, distinguishing when bonds are staggered or eclipsed.

Explore butane's Newman projections, identify four rotational isomers with methyl groups, and rank them from anti staggered to fully eclipsed, noting torsional and steric strain.

Explore cycloalkane rings, angle strain, and the chair conformation of cyclohexane, including flat Hayworth projections and a practical guide to drawing the chair and comparing projections.

Explore how chair substituents are defined as axial or equatorial, how flat projections relate to the top and bottom faces, and why equatorial positions favor stability over axial.

Explore the chair flip of cyclohexane, linking axial and equatorial positions to interconvert chair conformations, analyze stability and diaxial strain, and see how bulky groups like tert-butyl lock conformations.

Explore stereoisomers and chirality, distinguish chiral and non-chiral carbons, and learn to assign R and S configurations using wedges and dashes.

Identify chiral carbons in larger molecules by checking sp3 centers with four unique substituents, distinguish swapping chirality from rotation, and understand R/S states and stereoisomer concepts.

Learn the CIP rules for prioritizing chiral carbon substituents, determine R or S configurations, and handle rings and double/triple bonds using atomic-number priority and ghost-bonding concepts.

Determine absolute configuration of chiral carbons by applying priority rules, placing the fourth priority behind the page, and using circle drawings to assign R or S, including Fisher projection.

Translate the Fischer projection into three-dimensional space and identify chiral centers and assign R/S configurations, with practice distinguishing anomer and diastereomers.

Explore stereoisomers in organic chemistry, focusing on enantiomers and diastereomers, the 2^n rule for chiral carbons, R/S configurations, and racemic mixtures, plus E-Z diastereomerism.

Explore E and Z stereochemistry for alkenes using priority rules to label high-priority groups and determine cis or trans configurations. Understand how non-rotating double bonds create diastereomers and meso compounds.

Explore meso compounds as a key exception to chirality, examining internal symmetry, chiral carbons, and enantiomers, then contrast with diastereomers and constitutional isomers through practice problems.

Explore defining acids and acidic hydrogens, including conjugate bases and hydronium formation, via Bronsted-Lowry and Lewis concepts, mechanisms, and pKa-based acidity.

Explore how pKa indicates acidity by applying the negative log of Ka, rank hydrogens using pKa values, and predict reaction direction from strongest to weakest acid.

Compare conjugate bases to assess acidity, cancel water and hydronium, and apply four stability trends to identify the strongest acid without using pKa.

Explore how polarizability and resonance shape acidity by comparing halogen conjugate bases, noting fluorine’s localized charge vs bromine’s delocalized charge, and how stability governs acid strength.

Explore hybridization and inductive effects as acidity trends in sp3, sp2, and sp carbons. Understand their conjugate bases and pKa, and how electronegative atoms or carbon donation influence acidity.

Explore basicity as the mirror of acidity, applying polarizability, resonance, hybridization, and inductive trends to judge base strength, with hydroxide formation and negative-charge instability driving reactivity.

Explore the difference between reaction schemes and mechanisms, learn concerted and multi-step mechanisms with intermediates, and master arrow conventions for electron movement.

Use the ABC principle to study organic chemistry—A for reactants, B for reagents, C for product—emphasizing recognition and recall with an ABC document and preparation for radical halogenation questions.

Explore the radical concept as a single unpaired electron, its instability, and how homolytic cleavage forms radicals like chlorine, with a look at radical resonance and future halogenation.

Explain the radical halogenation mechanism through initiation, propagation, and termination, using bromine as the example and hydrogen abstraction to form alkyl bromide via a carbon radical.

Explore radical halogenation regioselectivity by comparing primary, secondary, tertiary, and benzylic radicals. Apply mechanistic insights to predict the best hydrogen to brominate and the resulting alkyl bromide.

Introduce the framework for OChem I reactions, starting with radical halogenation to form alkyl halides, then substitution, elimination to alkenes, and alkene additions, with practice problems on radical halogenation.

Explore the SN2 reaction mechanism, identifying nucleophiles and leaving groups, and understand its one-step, bimolecular rate law with substrate and nucleophile concentrations.

Explore the SN2 backside attack and stereospecificity, using molecular orbital theory to explain why nucleophiles attack antibonding orbitals and swap wedge and dash configurations.

Explore the SN1 reaction: a two-step, unimolecular substitution forming a carbocation intermediate and racemic products, with implications for reaction rate and possible rearrangements.

Explore carbocation rearrangements, focusing on the hydride shift mechanism, how rearrangements improve carbocation stability from secondary to tertiary, and applying this to SN1 reactions with practical examples.

Explore the methyl shift, a carbocation rearrangement in organic chemistry i, showing how a methyl moves near a quaternary carbon to stabilize the cation, with SN1 behavior and ring resizing.

Explore how substrate dictates SN2 versus SN1, using a flowchart to assess primary, secondary, and tertiary alkyl halides, nucleophile strength, and solvent effects including protic and aprotic media.

Explore the E2 elimination mechanism that converts alkyl halides into alkenes via a concerted, base-driven process, highlighting alpha hydrogens, antiperiplanar geometry, and differences from E1 and SN2.

Explore how antiperiplanar orientation enables e2 eliminations by aligning the carbon–bromine antibonding orbital with the carbon–hydrogen bonding orbital, with rotation or ring constraints affecting feasibility.

Explain how kinetic and thermodynamic products arise in E2 eliminations by comparing attack ease, alkene stability, and the role of bulky versus small bases.

Explore dehydration as an elimination via the E2 mechanism, converting a poor hydroxyl leaving group with tosyl chloride or acid, leading to the Zaitsev product, the most substituted alkene.

Master the E1 mechanism of elimination, carbocation intermediates, rearrangements like hydride shifts, and how E1 compares with E2 in product outcomes, focusing on tertiary and benzylic carbons.