Organic Chemistry Practice
Interactive practice tools with instant feedback on key topics to help you master organic chemistry.
Functional Groups and Nomenclature 6
- Determine a Molecular Formula Count atoms from line-angle structures and check your answer instantly.
- IUPAC Nomenclature Name organic compounds systematically with personalized feedback to incorrect answers.
- Nomenclingo (IUPAC Name Builder) Build IUPAC names piece by piece from a structure in this interactive naming game.
- Guided IUPAC Naming Beta Learn the IUPAC naming algorithm step by step: identify the FG, select the parent chain, find substituents, and number.
- Functional Group Identification Spot every functional group in a molecule before checking your answer.
- Functional Group Classification Classify a highlighted functional group with its full label: modifier and base group.
Resonance 3
- Identify Aromaticity Determine whether ring systems are aromatic, antiaromatic, or nonaromatic.
- Compare Resonance Contributors Determine which resonance form is the more significant contributor.
- Resonance Arrows Draw curved arrows showing electron movement between resonance forms.
Acids and Bases 3
- pKa Comparison (DMSO) Pick the more acidic compound from two structures and learn pKa values in DMSO.
- pKa Comparison (Water) Pick the more acidic compound using pKa values in water.
- Find the Acidic Proton Click on the most acidic atom in each molecule. Covers O–H, N–H, and C–H acids.
Arrow Drawing 1
- Mechanism Arrows Learn to draw curved arrows for common organic mechanism steps.
Stereochemistry 6
- Assign R or S Stereochemistry Assign R or S to chiral centers using an interactive 3D model.
- Assign E or Z Stereochemistry Determine E/Z configuration of alkenes using Cahn-Ingold-Prelog priority rules.
- Identify meso Compounds Identify meso compounds by finding internal planes of symmetry.
- Stereoisomer Relationships Classify pairs of molecules as enantiomers, diastereomers, or identical.
- Isomer Relationships Beta Two molecules, one formula: structural isomers, enantiomers, diastereomers, or identical?
- Molecule Relationships Beta Classify molecule pairs: different molecules, structural isomers, resonance forms, enantiomers, diastereomers, conformations, or identical.
Fischer Projections 3
- Fischer Projections: Assign R/S Beta Assign R/S from Fischer projections, including the horizontal-bond reversal rule, sugars, and amino acids.
- Fischer Projections: Compare & Convert Beta Practice the legal moves: classify Fischer pairs, and match Fischer projections to line-angle drawings.
- Fischer Projections: Meso or Chiral Beta Spot the internal mirror plane in a Fischer projection, or show the molecule is chiral.
Conformations 5
- Newman Projections: Identify Identify anti, gauche, and eclipsed conformations on sight.
- Newman Projections: Build Translate wedge-dash structures by placing substituents interactively.
- Newman Projections: Rotate Rotate Newman projections to match with line-angle drawings.
- Chair Conformations: Ring Flip Place substituents in the correct axial or equatorial positions on a flipped chair. Easy, Medium, and Hard difficulty modes.
- Chair Conformations: Energy Compare chair conformers and pick the more stable one using A-values.
Boiling & Melting Points 4
- Which Boils Higher? Two structures, measured boiling points: pick the higher, then name the deciding force.
- Which Melts Higher? Compare measured melting points, where crystal packing matters as much as attraction.
- Boiling Point Trends Drag three structures into boiling-point order: each set varies exactly one feature — chain length, branching, halogen size, O–H count, or force class.
- Boiling vs Melting Inversions Pairs where the two properties disagree: one compound boils higher, the other melts higher.
NMR Spectroscopy: Concepts 6
- Count ¹H NMR Signals Predict how many distinct signals a compound shows in its ¹H NMR spectrum, with color-coded equivalent-proton answer keys.
- Count ¹³C NMR Signals Predict the number of distinct ¹³C NMR signals, with color-coded equivalent-carbon answer keys.
- Find Equivalent Protons Click every position that is chemically equivalent to a highlighted atom and learn homotopic, enantiotopic, and diastereotopic relationships.
- Predict Splitting Patterns Apply the n+1 rule to predict multiplicity, from singlets to septets, with worked explanations.
- Predict Complex Splitting (dd, dt) Name compound multiplets where the J values genuinely differ, with splitting-tree answer keys.
- Match the Molecule to the Integration Given a ¹H NMR integration ratio, pick which of three candidate structures fits its proton partition.
NMR Spectroscopy: Reading Spectra 4
- Assign ¹H NMR Spectra Match every signal in a spectrum reconstructed from published experimental data to the protons that produce it, with zoomable multiplets.
- Assign ¹³C NMR Spectra Match each line in a proton-decoupled ¹³C spectrum to its carbon; crowded regions are shown but honestly left unasked.
- NMR Integration: Match the Spectrum Three candidate structures all share the same ¹H NMR integration ratio — read the chemical shifts and splitting on the spectrum to pick the one that fits.
- DEPT Practice: Classify Every Carbon Read ¹³C, DEPT-90, and DEPT-135 spectra together and classify each carbon as CH₃, CH₂, CH, or quaternary.
Mass Spectrometry 4
- Nitrogen Rule Read the nominal mass of M⁺• and call the strongest claim it supports about the nitrogen count.
- Degrees of Unsaturation Turn a molecular formula into its ring + π-bond count, then find every degree on the revealed structure.
- Isotope Patterns Read the M+2 cluster to identify Cl/Br content, or count carbons from the M+1 peak.
- Exact Mass (HRMS) Real published HRMS values, two directions: identify the adduct from a known formula, or pin the formula down to millidaltons.
IR Spectroscopy 4
- Assign the Band One band highlighted on a real IR spectrum — name the stretch it belongs to.
- Spot the Group Structure hidden, spectrum shown: call the functional group the bands demand.
- Predict the Bands From the structure, call which bands the real spectrum shows — and which tempting bands stay silent.
- Match the Structure One real spectrum, four structures: eliminate the three the band data rules out.
General Chemistry Practice
Build intuition for core general chemistry concepts with interactive practice problems and instant feedback.
Atoms & Measurement 4
- Subatomic Particles Find the number of protons, neutrons, and electrons for any element or ion.
- Significant Figures Count sig figs and round answers correctly in calculation problems.
- Dimensional Analysis Convert between units using dimensional analysis with step-by-step practice.
- Electron Configuration Write electron configurations for atoms and ions using the Aufbau principle.
Bonding & Structure 2
- Lewis Structures Draw Lewis dot structures for molecules and ions interactively.
- Molecular Geometry (VSEPR) Predict molecular shapes and bond angles using VSEPR theory.
Periodic Trends & Reactions 5
- Atomic & Ionic Size Compare atomic and ionic radii across the periodic table.
- Periodic Trends (IE, EN, EA) Compare ionization energy, electronegativity, and electron affinity across elements.
- Oxidation Numbers Assign oxidation states to atoms in compounds and ions.
- Balancing Equations Balance chemical equations one coefficient at a time.
- Le Chatelier's Principle Predict how equilibrium shifts in response to changes in conditions.
Naming & Formulas 2
- Naming Compounds Name ionic, covalent, and acid compounds from their formulas.
- Polyatomic Ions Memorize polyatomic ion names and formulas with flashcard-style practice.
Stoichiometry & Solutions 4
- Mole Conversions Convert between moles, grams, and particles step by step.
- Limiting Reagent Identify limiting reagents and calculate theoretical yields.
- Dilution (M₁V₁=M₂V₂) Solve dilution problems using the M1V1=M2V2 equation.
- Gas Laws Solve ideal gas law, combined gas law, and partial pressures problems.
Acids, Bases & Thermo 3
- Acid/Base Strength Compare acid and base strength using structure and periodic trends.
- Thermochemistry Solve enthalpy, Hess's law, and calorimetry problems.
- Nuclear Chemistry Solve nuclear decay, half-life, and nuclear equation balancing problems.
Literature Reactions
Tired of too-simple and made-up organic reactions that look nothing like actual exam problems? Here are real reactions from the scientific literature, drawn as complete schemes: starting materials, conditions, and products, with the yield and reference where the source reports them. Sort them by mechanism, as our worksheets do, or by functional group, as most textbooks do. Use them to practice predicting the product or to hone your mechanism drawing skills.
Substitution & Elimination Reactions
Aliphatic nucleophilic substitution 13
- Alcohol to alkyl halide 15 examples
- Leaving-group displacement 8 examples
- N-Alkylation 8 examples
- Williamson ether synthesis 8 examples
- Epoxide opening 7 examples
- S-Alkylation 6 examples
- Carboxylate alkylation 3 examples
- Ether cleavage 3 examples
- Acetylide alkylation 2 examples
- Epoxide from halohydrin 1 example
- Finkelstein reaction 1 example
- Grignard alkylation 1 example
- O-Silylation 1 example
Substitution & Elimination Reactions
Elimination 9
- Elimination to alkyne 11 examples
- Leaving-group elimination 11 examples
- Dehydration of alcohols 7 examples
- Hofmann elimination 2 examples
- Aryne formation 1 example
- Cope elimination 1 example
- Decarboxylative elimination 1 example
- Oxime to nitrile 1 example
- Retro-oxa-Michael 1 example
Addition to Alkenes & Alkynes
Addition to alkenes and alkynes 12
- Halogenation 10 examples
- Cyclopropanation 9 examples
- HX addition 7 examples
- Hydrogenation 6 examples
- Oxymercuration 5 examples
- Epoxidation 4 examples
- Halohydrin formation 3 examples
- Dihydroxylation 2 examples
- Haloetherification 2 examples
- Hydroboration 2 examples
- Alkyne hydration 1 example
- Oxidative cleavage 1 example
Pericyclic Reactions
Diels–Alder and other cycloadditions 5
- Diels–Alder reaction 10 examples
- Hetero-Diels–Alder 1 example
- Retro-Diels–Alder 2 examples
- [2+2] cycloaddition 1 example
- Cheletropic extrusion 2 examples
Pericyclic Reactions
Electrocyclic reactions 2
- 4π electrocyclization 5 examples
- 6π electrocyclization 6 examples
Pericyclic Reactions
Sigmatropic rearrangements 3
- [1,5]-H shift 2 examples
- Claisen rearrangement 2 examples
- Other sigmatropic 1 example
Radical Reactions
Radical reactions 5
- Benzylic halogenation 8 examples
- Allylic halogenation 4 examples
- Radical cyclization 3 examples
- Radical dehalogenation 2 examples
- Radical addition 1 example
Aromatic Chemistry
Electrophilic aromatic substitution 9
- Halogenation 16 examples
- Nitration 12 examples
- Friedel–Crafts acylation 10 examples
- Friedel–Crafts alkylation 6 examples
- Friedel–Crafts cyclization 6 examples
- Sulfonation 3 examples
- Azo coupling 2 examples
- Desulfonation 1 example
- Other EAS 1 example
Aromatic Chemistry
Diazonium chemistry 4
- Sandmeyer reaction 9 examples
- Deamination 1 example
- Aryl azide formation 1 example
- Azo coupling 2 examples
Aromatic Chemistry
Oxidation and reduction of aromatic compounds 5
- Benzylic oxidation 4 examples
- Benzylic halogenation 8 examples
- Nitro reduction 6 examples
- Clemmensen reduction 3 examples
- Birch reduction 4 examples
Carbonyl Chemistry
Nucleophilic addition to aldehydes and ketones 13
- Grignard addition 19 examples
- Acetal formation 10 examples
- Hydrate formation 6 examples
- Organolithium addition 5 examples
- Acetal hydrolysis 3 examples
- Cyanohydrin formation 3 examples
- Hydride reduction 3 examples
- Imine formation 3 examples
- Reductive amination 3 examples
- Strecker synthesis 2 examples
- Aminal formation 1 example
- Cannizzaro reaction 1 example
- Hemiacetal formation 1 example
Carbonyl Chemistry
Nucleophilic acyl substitution 14
- Amide formation 16 examples
- Acid chloride formation 9 examples
- Fischer esterification 8 examples
- Nitrile hydrolysis 7 examples
- Amide to nitrile 6 examples
- Saponification 5 examples
- Amide hydrolysis 4 examples
- Ester from acid chloride 4 examples
- Anhydride formation 3 examples
- Other acyl substitution 2 examples
- Anhydride opening 2 examples
- Lactamization 2 examples
- Transesterification 2 examples
- Carbamate formation 1 example
Enol & Enolate Chemistry
Enols and enolate formation (fundamentals) 9
- Keto–enol tautomerization 4 examples
- Silyl enol ethers 4 examples
- Kinetic enolates 3 examples
- Alkene isomerization 2 examples
- Enamines 2 examples
- Enol esters 2 examples
- Thermodynamic enolates 2 examples
- Imine–enamine tautomerization 1 example
- Lactam–lactim tautomerization 1 example
Enol & Enolate Chemistry
Enolate alkylation 2
- Enolate C-alkylation 9 examples
- Malonic ester synthesis 2 examples
Enol & Enolate Chemistry
Alpha-halogenation 5
- α-Halogenation (acidic) 13 examples
- Hell–Volhard–Zelinsky 8 examples
- Haloform reaction 2 examples
- α-Halogenation (basic) 1 example
- Silyl enol ether halogenation 1 example
Enol & Enolate Chemistry
Aldol and related condensations 6
- Intramolecular aldol 11 examples
- Aldol condensation 6 examples
- Aldol addition 4 examples
- Knoevenagel condensation 2 examples
- Mannich reaction 2 examples
- Darzens condensation 1 example
Enol & Enolate Chemistry
Claisen condensations and enolate acylation 3
- Claisen condensation 9 examples
- Dieckmann condensation 4 examples
- Enolate C-acylation 4 examples
Enol & Enolate Chemistry
Conjugate addition, annulation, cascades 4
- Robinson annulation 9 examples
- Michael addition 7 examples
- Decarboxylation 5 examples
- Enolate cascades 1 example
Redox, Rearrangements & Organometallics
Oxidations and reductions 13
- Alcohol oxidation 7 examples
- Nitro reduction 6 examples
- Aldehyde oxidation 4 examples
- Benzylic oxidation 4 examples
- Birch reduction 4 examples
- Clemmensen reduction 4 examples
- Ester / amide reduction 4 examples
- Wolff–Kishner reduction 2 examples
- Aromatization 1 example
- Dakin oxidation 1 example
- Disulfide formation 1 example
- Imine reduction 1 example
- Nitrile reduction 1 example
Redox, Rearrangements & Organometallics
Rearrangements 5
- Curtius rearrangement 2 examples
- Pinacol rearrangement 2 examples
- Beckmann rearrangement 1 example
- Hofmann rearrangement 1 example
- Schmidt reaction 1 example
Redox, Rearrangements & Organometallics
Organometallic reagents and cross-coupling 5
- Grignard formation 7 examples
- Acetylide formation 1 example
- Grignard protonolysis 1 example
- Ullmann coupling 1 example
- Wurtz coupling 1 example
Alkanes and radical reactions
Radical reactions 5
- Benzylic halogenation 8 examples
- Allylic halogenation 4 examples
- Radical cyclization 3 examples
- Radical dehalogenation 2 examples
- Radical addition 1 example
Alkyl halides: substitution and elimination
Aliphatic nucleophilic substitution 13
- Alcohol to alkyl halide 15 examples
- Leaving-group displacement 8 examples
- N-Alkylation 8 examples
- Williamson ether synthesis 8 examples
- Epoxide opening 7 examples
- S-Alkylation 6 examples
- Carboxylate alkylation 3 examples
- Ether cleavage 3 examples
- Acetylide alkylation 2 examples
- Epoxide from halohydrin 1 example
- Finkelstein reaction 1 example
- Grignard alkylation 1 example
- O-Silylation 1 example
Alkyl halides: substitution and elimination
Elimination 9
- Elimination to alkyne 11 examples
- Leaving-group elimination 11 examples
- Dehydration of alcohols 7 examples
- Hofmann elimination 2 examples
- Aryne formation 1 example
- Cope elimination 1 example
- Decarboxylative elimination 1 example
- Oxime to nitrile 1 example
- Retro-oxa-Michael 1 example
Alkenes and alkynes
Addition to alkenes and alkynes 12
- Halogenation 10 examples
- Cyclopropanation 9 examples
- HX addition 7 examples
- Hydrogenation 6 examples
- Oxymercuration 5 examples
- Epoxidation 4 examples
- Halohydrin formation 3 examples
- Dihydroxylation 2 examples
- Haloetherification 2 examples
- Hydroboration 2 examples
- Alkyne hydration 1 example
- Oxidative cleavage 1 example
Dienes and pericyclic reactions
Diels–Alder and other cycloadditions 5
- Diels–Alder reaction 10 examples
- Hetero-Diels–Alder 1 example
- Retro-Diels–Alder 2 examples
- [2+2] cycloaddition 1 example
- Cheletropic extrusion 2 examples
Dienes and pericyclic reactions
Electrocyclic reactions 2
- 4π electrocyclization 5 examples
- 6π electrocyclization 6 examples
Dienes and pericyclic reactions
Sigmatropic rearrangements 3
- [1,5]-H shift 2 examples
- Claisen rearrangement 2 examples
- Other sigmatropic 1 example
Aromatic compounds
Electrophilic aromatic substitution 9
- Halogenation 16 examples
- Nitration 12 examples
- Friedel–Crafts acylation 10 examples
- Friedel–Crafts alkylation 6 examples
- Friedel–Crafts cyclization 6 examples
- Sulfonation 3 examples
- Azo coupling 2 examples
- Desulfonation 1 example
- Other EAS 1 example
Aromatic compounds
Oxidation and reduction of aromatic compounds 5
- Benzylic oxidation 4 examples
- Benzylic halogenation 8 examples
- Nitro reduction 6 examples
- Clemmensen reduction 3 examples
- Birch reduction 4 examples
Aldehydes and ketones
Nucleophilic addition to aldehydes and ketones 13
- Grignard addition 19 examples
- Acetal formation 10 examples
- Hydrate formation 6 examples
- Organolithium addition 5 examples
- Acetal hydrolysis 3 examples
- Cyanohydrin formation 3 examples
- Hydride reduction 3 examples
- Imine formation 3 examples
- Reductive amination 3 examples
- Strecker synthesis 2 examples
- Aminal formation 1 example
- Cannizzaro reaction 1 example
- Hemiacetal formation 1 example
Carboxylic acids and their derivatives
Nucleophilic acyl substitution 14
- Amide formation 16 examples
- Acid chloride formation 9 examples
- Fischer esterification 8 examples
- Nitrile hydrolysis 7 examples
- Amide to nitrile 6 examples
- Saponification 5 examples
- Amide hydrolysis 4 examples
- Ester from acid chloride 4 examples
- Anhydride formation 3 examples
- Other acyl substitution 2 examples
- Anhydride opening 2 examples
- Lactamization 2 examples
- Transesterification 2 examples
- Carbamate formation 1 example
Enols, enolates, and carbonyl condensations
Enols and enolate formation (fundamentals) 9
- Keto–enol tautomerization 4 examples
- Silyl enol ethers 4 examples
- Kinetic enolates 3 examples
- Alkene isomerization 2 examples
- Enamines 2 examples
- Enol esters 2 examples
- Thermodynamic enolates 2 examples
- Imine–enamine tautomerization 1 example
- Lactam–lactim tautomerization 1 example
Enols, enolates, and carbonyl condensations
Enolate alkylation 2
- Enolate C-alkylation 9 examples
- Malonic ester synthesis 2 examples
Enols, enolates, and carbonyl condensations
Alpha-halogenation 5
- α-Halogenation (acidic) 13 examples
- Hell–Volhard–Zelinsky 8 examples
- Haloform reaction 2 examples
- α-Halogenation (basic) 1 example
- Silyl enol ether halogenation 1 example
Enols, enolates, and carbonyl condensations
Aldol and related condensations 6
- Intramolecular aldol 11 examples
- Aldol condensation 6 examples
- Aldol addition 4 examples
- Knoevenagel condensation 2 examples
- Mannich reaction 2 examples
- Darzens condensation 1 example
Enols, enolates, and carbonyl condensations
Claisen condensations and enolate acylation 3
- Claisen condensation 9 examples
- Dieckmann condensation 4 examples
- Enolate C-acylation 4 examples
Enols, enolates, and carbonyl condensations
Conjugate addition, annulation, cascades 4
- Robinson annulation 9 examples
- Michael addition 7 examples
- Decarboxylation 5 examples
- Enolate cascades 1 example
Amines
Diazonium chemistry 4
- Sandmeyer reaction 9 examples
- Deamination 1 example
- Aryl azide formation 1 example
- Azo coupling 2 examples
Organometallic reagents and cross-coupling
Organometallic reagents and cross-coupling 5
- Grignard formation 7 examples
- Acetylide formation 1 example
- Grignard protonolysis 1 example
- Ullmann coupling 1 example
- Wurtz coupling 1 example
Oxidations and reductions across chapters
Oxidations and reductions 13
- Alcohol oxidation 7 examples
- Nitro reduction 6 examples
- Aldehyde oxidation 4 examples
- Benzylic oxidation 4 examples
- Birch reduction 4 examples
- Clemmensen reduction 4 examples
- Ester / amide reduction 4 examples
- Wolff–Kishner reduction 2 examples
- Aromatization 1 example
- Dakin oxidation 1 example
- Disulfide formation 1 example
- Imine reduction 1 example
- Nitrile reduction 1 example
Rearrangements
Rearrangements 5
- Curtius rearrangement 2 examples
- Pinacol rearrangement 2 examples
- Beckmann rearrangement 1 example
- Hofmann rearrangement 1 example
- Schmidt reaction 1 example
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Study Guides
Study Guides New
Concise, professor-written guides that pair with the practice above — read the concept, see live examples from our problem bank, then go practice.
- Isomers and Stereochemistry Chirality, enantiomers vs diastereomers, meso compounds, CIP rules, R/S and E/Z.
- pKa and Acid–Base Chemistry Conjugate pairs, predicting equilibria, and the six factors that control acidity.
- Electrophilic Aromatic Substitution The five classic reactions, the arenium mechanism, and directing effects.
- All study guides →
More On The Way
Reactions
Interactive practice for product prediction under development.