Organic Chemistry I - Complete Master Class

Learn to name alkanes using prefix, parent, and suffix to denote substitutions, the longest carbon chain, and the main functional group, with alphabetical ordering.

Compare how different attachments of substituent groups yield constitutional isomers, and how variations in three-dimensional orientation create stereoisomers, using wedge and dash representations to show spatial arrangement.

Learn rules for naming halogenated alkanes, including fluoro, chloro, bromo, and iodo substituents on the longest carbon chain; apply base naming, numbering to minimize locants, and alphabetical ordering of substituents.

Name alcohols by identifying the longest carbon chain, including the OH in the parent, then apply the -ol suffix with correct numbering and substituents like methyl and ethyl.

Explore how to name amines, including methylamine, diethyl, and triethyl, and determine nitrogen substitutions on the parent chain using simple rules.

This lecture uses Newman projections to compare tetrahedral carbon geometry, explaining wedge and dash models, gauche and anti orientations, and eclipsed conformations with energy diagrams.

Show how to draw Newman projections of butane from a specific perspective, identifying anti orientation, gauss position, and eclipse conformations, and explain their energy changes via an energy diagram.

Explore cyclohexane structures, compare linear and cyclic naming, and master chair conformations, axial and equatorial hydrogens, and ring flips to minimize strain.

In cyclohexane chair conformations, equatorial positions are more stable than axial ones. The molecule favors equatorial placement to minimize unstable interactions and energy.

Learn to name alkenes using chain length, double bond location, and ring notation, including cyclohexane, while choosing numbering to minimize locants and applying cis/trans and E/Z stereochemistry.

Explore alkene reactivity with HBr, showing bromine attaching to carbon 2 and hydrogen transferring to carbon 1, with hydrogen balance and formal charge considerations.

Explore how nucleophiles, rich in electrons, attack electrophiles, which seek electrons, using arrow notation to map electron flow and predict reactions with examples like hydroxide, halogens, and boron species.

Explore how a nucleophile and a base can describe the same species, using hydroxide as an example, and see how reaction context, acid-base interactions, and arrow notation influence mechanisms.

Define mechanism as a step-by-step description of bond making and breaking, and illustrate the hydrohalogenation of ethene with HBr, detailing the acid-base step, arrow pushing, and nucleophile–electrophile roles.

Explore the differences between thermodynamics and kinetics in chemical reactions, using a reaction diagram and transition state to explain energy changes, stability, and product distribution.

Compare energy levels of reactants and products to show stability and when the equilibrium constant is >1, products are favored; when <1, reactants are favored.

Explore how activation energy and transition states dictate reaction speed, comparing high and low energy pathways, and identify intermediates and the rate-determining step in multi-step reactions.

Grasp how bond making and breaking reshapes molecular architectures through reaction mechanisms. Learn electron flow, electrophiles, and nucleophiles to master the core concepts of organic chemistry.

Examine how a more complicated alkene reacts with hbr and chlorine, showing two possible products and intermediates formed via arrow pushing on two possible carbon sites.

This lecture explains carbocation stability by comparing methyl, primary, secondary, and tertiary carbocations, emphasizing direct attachments to the charged carbon and applying this to intermediates D and E.

Use an energy diagram to determine whether B or C is the major product, via intermediates D and E from starting material A, noting tertiary carbocations are more stable.

Explain how energy barriers and transition states shape major and minor products, using A, D, E, B, and C. Lower energy to E favors C as the major product.

Predict the two possible bromination products from adding hydrogen bromide to an alkene and show they form in a 50/50 ratio due to equally stable secondary carbocation intermediates.

Master Markovnikov's rule as a quick plug-and-play for predicting addition products, linking electrophile attack to the carbon with the most hydrogens and nucleophile attack to the most substituted carbon.

Frame problems from multiple angles to predict reaction products in organic chemistry. Apply Markovnikov-type rules to identify the major product and improve reaction efficiency.

The lecture introduces carbon cation rearrangements in alkyne reactions with hydrogen halides, focusing on 1,2-hydride shifts that convert secondary cations to tertiary ones, predicting major vs minor products.

Explain why 1,3-hydride shifts do not occur in carbocation rearrangements and how two 1,2 shifts and Markovnikov considerations shape the major product.

Explore ring expansions that rearrange a charged intermediate via hydride and methyl shifts. See how the resulting carbocation drives bromination to a major, larger-ring product with increasing stability.

The lecture explains that alkenes react with water only under acid catalysis, since water is too weak an acid; h3o+ enables hydration to form an alcohol.

Demonstrates acid-catalyzed hydration of alkenes, where a proton from the catalyst activates the double bond, water attacks to form an alcohol, and deprotonation yields the product.

Demonstrates the correct stepwise mechanism for water adding to alkenes to form alcohols, highlighting why multi-step arrow pushing beats single-step deprotonation, and explaining acidity via pKa.

Explore how acid-catalyzed reactions convert alcohol formation into ether formation by using another alcohol instead of water, highlighting a shared three-step mechanism and the catalyst's role.

Learn bromine addition to alkenes to form a vicinal dibromide in the overall reaction, with no catalyst, as two bromines attach across the double bond.

This lecture covers the mechanism of bromination of alkenes, detailing a two-step process with a bromonium ion intermediate, bond formation to carbon and simultaneous Br–Br bond cleavage.

Examine how Br2 adds to alkenes through a carbocation mechanism, using hydride shifts to stabilize intermediates and shape the final brominated product, with evidence favoring the promoting ion mechanism.

Explore halohydrin formation from alkenes using Br2 in excess water, yielding major product A with hydroxide on C2 and bromine on C1, and minor product B.

analyze the halohydrin formation mechanism, showing water acting as the nucleophile to form two products at carbon 1 and 2, with one as the major product.

Explore halohydrin formation and regioselectivity as water attacks either carbon 1 or 2, explaining the A and B product distribution through a carbocation-based rationale and energy diagram.

Explore hydroboration as the complementary hydration pathway in organic chemistry, contrasting it with oxymercuration and acid-catalyzed hydration, highlighting rearrangement-free alcohol formation at the less substituted carbon.

Explore epoxide formation via Parkside reaction with mcpba to convert alkenes into oxiranes, and hydrogenation of an alkyne using H2 and Pd/C to add hydrogens across carbons.

Explore hydrogenation of three alkenes with H2 and Pd/C, compare delta H diagrams, and show that more non-hydrogen substituents increase stability, while cis alkenes start higher and are less stable.

Master chirality by identifying sp3 carbons with four different groups, testing for non superimposed mirror images to classify Cairo objects and recognizing their importance in medicine.

Rank substitutes at a chiral center by atomic number, not size, to assign priority and break ties by the next atoms along the path, as shown with bromine and hydrogen.

Master ranking substituents, orienting the lowest priority group away, and determining R or S by tracing from priority 1 through 4 in clockwise or counterclockwise order.

Apply the single swap rule to swap two groups while keeping wedges and dashes fixed, revealing the R or S configuration and inversion of the original molecule.

Discover two ways to draw enantiomers: use the single swap rule to resolve S and R configurations, or construct a mirror image to show a non superimposed mirror relationship.

Revisit hbr bromination of alkenes under markovnikov control, showing bromine attaches to carbon 2 as major, creating a chiral center with r and s configurations and a racemic pair.

Explain the mechanism of HBr bromination with stereochemistry: base abstracts hydrogen at carbon 2, bromine attacks the p orbital from top or bottom, giving rs and rr in equal measure.

Revisit bromination with Br2 and analyze stereochemistry in three dimensions, using wedge and dash notation to show trans orientation and avoid common drawing pitfalls.

Demonstrates Br2 bromination with anti addition, using three-arrow mechanism, stereochemical indicators, and attack vectors to determine S/R at carbons 2 and 3.

Learn to assign R and S after Br2 anti addition, prioritize bromine over hydrogen, and use internal symmetry to identify meso products.

Explore the hydrogenation of an alkyne to an alkane using H2 and a palladium on carbon catalyst, highlighting syn (sin) addition and stereochemical outcomes with wedge/dash visualization and R/S designations.

Apply CIP rules to rank substituents and assign R or S configurations in a stereochemical hydrogenation analysis. Show how a mirror image inverts S and R.

Apply the single swap rule to determine the R or S configuration in hydrogenation syn addition, using a hydrogen-methyl swap to place the lowest-priority group away and account for inversion.

Learn epoxidation of alkenes via syn addition, forming epoxides with two possible top or bottom oxygen additions, yielding distinct stereochemical outcomes (R vs S) from different attack orientations.

explains hydroboration, a syn addition to alkenes from the same side, with anti-mark regioselectivity and stereo outcomes, using PH3, hydrogen peroxide, and hydroxide.

Learn how oxymercuration proceeds via a two-step mechanism with mercury acetate and water, then sodium borohydride, delivering anti addition and Markovnikov regiochemistry, contrasting with hydration.

Examine vinyl carbocations, distinguishing primary and secondary vinyl cations, and show that stability aligns with the number of groups attached to the cation center, not just carbon count.

Compare alkyne and alkane reactivity by reacting both with one equivalent of HBr, analyzing secondary carbocation formation and energy diagrams to show why alkynes are less reactive.

Explore the mechanism of alkyne HBr addition, using pi electrons as a base and Br− as a nucleophile, leading to vinyl bromide and germinal dibromide formation.

Explains why germinal termination occurs in the second reaction, showing how an intermediate favors bromine attack over hydrogen transfer and yields the germinal product through a more stable secondary carbon.

Explore acid-catalyzed hydration of alkynes using mercury sulfate, forming enol intermediates that tautomerize to a ketone; enol exists briefly in equilibrium with the ketone.

Perform hydroboration of alkynes with the bulky boron reagent DSP to achieve anti-markovnikov hydration, yielding enol that tautomerizes to aldehydes or ketones using hydrogen peroxide and hydroxide.

Explain hydrogenation of alkynes with H2 and palladium on carbon, and how it forms alkanes. Show two alkene-stopping methods: syn addition with Lindlar catalyst and anti addition dissolving metal reduction.

compare hydroxide and strong bases in deprotonating alkynes, noting pKa about 25 and that only a sufficiently strong base drives the equilibrium toward the negatively charged alkyne species.

Explore multi-step synthesis to extend alkynes by adding carbons through deprotonation and alkylation with ethyl bromide. See how two-step sequences build more complex molecules.

Learn how alcohols with a leaving group X undergo substitution or elimination when paired with a nucleophile or base, highlighting SN1 and SN2 mechanisms.

Show that SN1 rate depends on the leaving group concentration, not on the nucleophile, and that increased substitution stabilizes the carbocation, yielding inversion, retention, or racemic mixtures.

Explore how sn1 reactions proceed via a carbocation intermediate and a transition state, with polar solvents like water accelerating the reaction by stabilizing charges.

Explore SN2 general features: a one-step mechanism with simultaneous nucleophile attack and leaving group departure, rate depending on both nucleophile and substrate, and inversion of stereochemistry.

Explore how sn2 rates slow with increased substitution due to steric hindrance and stereo effects, and how leaving-group ability governs reaction speed, with iodine as best and fluorine as worst.

Explore nucleophilicity features in SN2 reactions, comparing good and bad nucleophiles, charge effects, and how substitution affects carbon attack. Across a period, nucleophilicity parallels basicity, with negative charges enhancing nucleophilicity.

Explore how nucleophilicity changes up and down the periodic table and how solvent choice, such as water versus DMSO, can invert basicity trends.

Four categories evaluate nucleophilicity and basicity, with examples of strong bases and good nucleophiles. LDA and tert-butoxide are poor nucleophiles but strong bases; conjugate acid pKa guides base strength.

Predicts that for methyl or primary alcohols, SN2 dominates due to unstable primary carbocations, while water acts as a poor nucleophile and polar solvents influence the reaction rate.

Explore SN1 and SN2 mechanisms across primary, secondary, and tertiary alcohol derivatives, highlighting how nucleophile strength, solvent, and concentration steer toward SN2 inversion or SN1 with racemization.

Explore E2 elimination, where a base removes a beta hydrogen to form an alpha–beta double bond in a concerted mechanism, yielding beta1 and beta2 products with base- and halide-dependent rates.

Apply Zaitsev's rule to predict the major E2 product by removing a beta hydrogen from the carbon with fewer hydrogens. Predict 80–90 percent of the time, with exceptions.

Explains E2 eliminations, showing how conjugation and steric effects decide whether Zaitsev or anti-Zaitsev products dominate, and how bulky bases can reverse this pattern.

Identify anti-periplanar and syn-periplanar hydrogen and bromine alignments as the only E2 pathways, with anti-periplanar fastest, gauche nonproductive, and the E isomer major over the Z.

Explore how chair conformation and ring flips control anti-periplanar arrangements for E2 elimination, and how tert-butyl substitutions bias equilibrium to speed or slow the reaction.

Explain the E1 elimination mechanism, forming a carbocation after the leaving group departs, then remove a beta hydrogen to yield the double bond, noting Zaitsev selectivity.

Explore how primary alkyl halides choose between sn2 and e2 pathways, evaluate nucleophile strength, base strength, solvent, and temperature, predict major products, and understand why sn1 and e1 are unlikely.

This lecture examines tertiary alkyl halides, showing SN2 is ruled out and E2 or SN1 paths dominate depending on base strength and nucleophile quality.

Explore how secondary alkyl halides react under different conditions, showing sn1/e1 pathways with poor nucleophiles in polar solvents, sn2 with strong nucleophiles, and e2 when strong base is present.

Explore electron localization and conjugation through resonance in nitro groups and carbon frameworks, and see how conjugation stabilizes acetaminophen and its conjugate base, enhancing acidity.

Activate alcohols via acid-catalyzed protonation of the hydroxyl group to convert hydroxide into a good leaving group like water, enabling nucleophilic substitution with bromine.

Learn to activate alcohols via SN1 and SN2 pathways using phosphorus tribromide and tosyl chloride under mild base conditions, avoiding rearrangements and controlling stereochemistry.

Explore activation of alcohols via phosphorus tribromide and via tosylate ester formation, showing two inversions with phosphorus tribromide giving overall retention, and a single inversion with the tosylate pathway.

Dehydrate alcohols via acid-catalyzed elimination with sulfuric acid and heat. Proceed via E1 for secondary and tertiary alcohols, yielding the stereochemical major product; primary alcohols do not form alkenes.

This lecture covers oxidation of alcohols using chromium trioxide and sulfuric acid to form chromic acid, converting secondary alcohols to ketones and primary to aldehydes, with PCC stopping at alcohol.

Explore acid-catalyzed substitution of epoxides and ethers, noting bromine attack at either carbon, with epoxides reacting readily at room temperature while ethers require heat due to strain-driven reactivity.

Explore epoxide reactivity under acidic and basic conditions, showing Markovnikov versus anti-Markovnikov opening. Learn how nucleophiles attack the most or least hindered carbon via SN1-like to SN2-like transitions.

Compare sulfur compounds to alcohols, showing how thiols share valence-shell configuration yet form strong mercury complexes, exhibit greater acidity, and display weaker hydrogen bonding with lower boiling points.

Explore how Grignard reagents form from alcohols using magnesium and ether, turning carbon into a nucleophile that adds to electrophiles, while noting moisture sensitivity and dry glassware requirements.

Compare coupling reactions such as Gilman reagents, lithium halogen exchange with copper iodide, and Suzuki and Heck reactions to form new carbon–carbon bonds beyond the green yard limitations.