How to Draw the Expected 1H NMR Spectrum (p. 25)

Organic Chemistry 1

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Gen Chem Review - Electrons, Bonding, & Molecular Properties — Topic Review (⏱️ <67 min)

Study Guide (fill this in as you watch the videos!)
Bonds, Lewis Structures, & Formal Charge (p. 3-6) (11:10)
Electronegativity, Induction, Molecular Polarity, & Bond Type (p. 7-9) (10:25)
Reading Bond-Line (Line-Angle) Structures (p. 10-11) (8:24)
Atomic Orbitals & Electron Configurations (p. 12-14) (4:13)
Valence Bond Theory & Molecular Orbital Theory (p. 15-16) (5:33)
Hybridization, Molecular Geometry, VSEPR Theory, Bond Strength, & Bond Length (p. 17-21) (14:43)
Intermolecular Forces, Physical Properties, & Solubility (p. 22-23) (4:10)
Constitutional Isomers (p. 24-26) (9:21)

Gen Chem Review - Electrons, Bonding, & Molecular Properties — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Lewis Structures Practice Exam Solutions (4:47)
Reading Bond-Line/Line-Angle Structures Practice Exam Solutions (3:19)
Hybridization, Molecular Geometry, & VSEPR Theory Practice Exam Solutions (17:58)
Intermolecular Forces Practice Exam Solutions (1:47)
Constitutional Isomers Practice Exam Solutions (11:38)

Bond-Line Structures, Functional Groups, Formal Charge, & Lone Pairs — Topic Review (⏱️ <42 min)

Study Guide (fill this in as you watch the videos!)
Ways of Representing Molecules (p. 3-4) (7:45)
Drawing Simple Bond-Line:Line-Angle Structures (p. 5-7) (11:24)
Functional Groups (p. 8-9) (9:17)
Bond-Line Drawings, Formal Charge, & Lone Pairs (p. 10-11) (13:01)

Bond-Line Structures, Functional Groups, Formal Charge, & Lone Pairs — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Drawing Bond-Line Structures Practice Exam Solutions (13:21)
Functional Groups Practice Exam Solutions (8:54)
Formal Charge & Lone Pairs Practice Exam Solutions (23:44)

Resonance & Curved Arrows — Topic Review (⏱️ <86 min)

Study Guide (fill this in as you watch the videos!)
Drawing Resonance Structures & Curved Arrows (p. 3-6) (14:00)
Formal Charges & Resonance Structures (p. 7-9) (12:21)
Quick Hacks for Drawing Resonance Structures (p. 10-11) (8:05)
Allylic Lone Pairs (p. 12-13) (7:59)
Allylic Carbocations (p. 14-15) (6:33)
Lone Pairs Next to Positive Charges (p. 16) (3:59)
Pi Bonds Between Atoms with Different Electronegativity (p. 17) (3:31)
Conjugated Pi Bonds Enclosed in a Ring (p. 18) (1:14)
Which Resonance Structure is Most Important? (p. 19-21) (8:40)
Drawing Resonance Hybrids (p. 22-24) (10:42)
Delocalized & Localized Lone Pairs (p. 25-28) (8:40)

Resonance & Curved Arrows — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Drawing Resonance Structures Practice Exam Solutions (49:53)
Lone Pairs, Hybridization, & Geometry Practice Exam Solutions (20:46)

Acids & Bases — Topic Review (⏱️ <97 min)

Study Guide (fill this in as you watch the videos!)
Review of Brønsted-Lowry Acids & Bases (p. 3-4) (6:41)
Curved Arrows & Flow of Electron Density (p. 5-6) (7:54)
Using pKa Values to Compare Acidity & Basicity (p. 7-14) (13:11)
Using pKa Values to Predict Equilibrium Position (p. 15-16) (5:32)
Factors that Affect Acidity & Anion Stability (p. 17-25) (23:29)
Factors that Affect Basicity & Cationic Stability (p. 26-30) (13:57)
Predicting Equilibrium Position without pKa Values (p. 31-34) (13:17)
The Leveling Effect (p. 35) (5:31)
The Solvating Effect (p. 36) (2:26)
Lewis Acids & Bases (p. 37-38) (4:04)

Acids & Bases — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Basics of Brønsted-Lowry Acids & Bases Practice Exam Solutions (5:13)
Curved Arrows with Acids & Bases Practice Exam Solutions (3:27)
Using pKa Values to Compare Acidity, Basicity, & Equilibrium Position Practice Exam Solutions (2:53)
Comparing Acidity & Basicity without pKa Values Practice Exam Solutions (20:49)
Predicting Equilibrium Position without pKa Values Practice Exam Solutions (13:04)
Lewis Acids & Bases Question Practice Exam Solutions (5:27)

Naming Alkanes — Topic Review (⏱️ <58 min)

Study Guide (fill this in as you watch the videos!)
Overview of Alkanes & Nomenclature (p. 3-4) (5:38)
Picking & Naming the Right Parent Chain (p. 5-8) (10:50)
Naming Substituents & Writing the Full Name (p. 9-14) (25:35)
Naming Bicyclic Compounds (p. 15-17) (15:52)

Naming Alkanes — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Naming Alkanes Practice Exam Solutions (28:16)

Properties of Alkanes & Cycloalkanes — Topic Review (⏱️ <88 min)

Study Guide (fill this in as you watch the videos!)
Constitutional Isomers of Alkanes (p. 3-5) (8:58)
Conformations/Conformers & Newman Projections (p. 6-8) (14:44)
Conformations/Conformers of Ethane, Propane, & Butane (p. 9-14) (16:32)
Properties of Cycloalkanes (p. 15-16) (6:29)
Cyclohexane Conformations Overview (p. 17-18) (3:14)
How to Draw Chair Conformations of Cyclohexane (p. 19-23) (15:03)
Substituted Cyclohexane (p. 24-27) (17:28)
cis-trans Stereoisomerism (p. 28) (4:54)

Properties of Alkanes & Cycloalkanes — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Constitutional Isomers of Alkanes Practice Exam Solutions (5:28)
Newman Projections Practice Exam Solutions (26:59)
Conformational Analysis & Stability Practice Exam Solutions (20:30)

Stereoisomerism & Chirality — Topic Review (⏱️ <93 min)

Study Guide (fill this in as you watch the videos!)
Isomerism Overview (p. 3-4) (3:54)
Chiral Centers & Enantiomers (p. 5-8) (14:45)
How to Assign R & S Configurations (p. 9-12) (16:00)
Optical Activity & Enantiomeric Excess (p. 13-15) (13:19)
Enantiomers vs. Diastereomers (p. 16-18) (6:57)
Symmetry, Chirality, & Meso Compounds (p. 19-21) (13:31)
Fischer Projections (p. 22-27) (16:28)
Chiral Compounds with No Chiral Center (p. 28-29) (4:35)
E & Z Designations for Alkenes (p. 30-31) (3:33)

Stereoisomerism & Chirality — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Chiral Centers & Enantiomers Practice Exam Solutions (25:16)
Enantiomeric Excess Practice Exam Solutions (3:49)
Enantiomers, Diastereomers, & Meso Compounds Practice Exam Solutions (21:05)
Fischer Projections Practice Exam Solutions (24:43)
E & Z, cis and trans Designations for Alkenes Practice Exam Solutions (2:34)

Thermodynamics, Kinetics, & Energy Diagrams — Topic Review (⏱️ <44 min)

Study Guide (fill this in as you watch the videos!)
Enthalpy, Entropy, & Gibbs Free Energy (p. 3-7) (15:20)
Equilibrium & Gibbs Free Energy (p. 8-9) (6:41)
Kinetics (p. 10-11) (8:29)
Energy Diagrams & the Hammond Postulate (p. 12-15) (13:08)

Thermodynamics, Kinetics, & Energy Diagrams — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Enthalpy, Entropy, & Gibbs Free Energy Practice Exam Solutions (2:56)
Equilibrium & Gibbs Free Energy Practice Exam Solutions (2:30)
Energy Diagrams & The Hammond Postulate Practice Exam Solutions (5:17)

Mechanisms, Curved Arrows, & Chemical Reactivity — Topic Review (⏱️ <45 min)

Study Guide (fill this in as you watch the videos!)
Nucleophiles & Electrophiles (p. 3-5) (12:52)
Mechanisms & Main Arrow Pushing Patterns (p. 6-12) (20:49)
How to Predict Carbocation Rearrangements (p. 13-15) (10:47)

Mechanisms, Curved Arrows, & Chemical Reactivity — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Nucleophiles & Electrophiles Practice Exam Solutions (3:45)
Mechanisms Basics Practice Exam Solutions (8:43)
Carbocation Rearrangements Practice Exam Solutions (4:17)

Alkyl Halides, Substitution, & Elimination Reactions — Topic Review (⏱️ <144 min)

Study Guide (fill this in as you watch the videos!)
Leaving Groups, Substitution & Elimination Reactions Overview (p. 3-5) (7:09)
Naming & Classifying Alkyl Halides/Haloalkanes (p. 6-8) (7:11)
SN2 & SN1 Reactions Overview (p. 9-11) (8:29)
Factors that Affect Substitution Reaction Rates & Protic vs. Aprotic Solvents (p. 12-16) (19:10)
E2 & E1 Reactions Overview & Stability of Alkenes (p. (7:41)
Regiochemistry & Stereochemistry of E2 Reactions (p. 20-26) (25:25)
E1 & SN1 (Unimolecular) Processes & Solvolysis (p. 27-29) (11:19)
Predicting Products for Substitution vs. Elimination (p. 30-35) (17:45)
Substitution & Elimination with Alcohols & Sulfonates/Tosylates (p. 36-38) (11:19)
Synthesis Strategies with Substitution & Elimination Reactions (p. 39-49) (28:15)

Alkyl Halides, Substitution, & Elimination Reactions — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
SN2 & SN1 Reactions Practice Exam Solutions (12:47)
E2 & E1 Reactions Practice Exam Solutions (20:49)
Predicting Products Between Substitution & Elimination Practice Exam Solutions (9:23)
Substitution & Elimination with Alcohols & Tosylates Practice Exam Solutions (9:21)
Simple Synthesis Problems Practice Exam Solutions (6:22)

Alkenes & Addition Reactions — Topic Review (⏱️ <159 min)

Study Guide (fill this in as you watch the videos!)
Overview of Addition Reactions (p. 3-4) (4:12)
Naming & Classifying Alkenes (p. 5-7) (6:08)
Unsaturation Number & Properties of Alkenes (p. 8) (3:57)
Hydrohalogenation (p. 9-12) (15:59)
Hydration Reactions Overview (p. 13) (3:29)
Acid-Catalyzed Hydration (p. 14-16) (7:52)
Oxymercuration-Demercuration Hydration (p. 17-18) (5:46)
Hydroboration-Oxidation Hydration (p. 19-22) (9:33)
Catalytic Hydrogenation (p. 23-25) (6:19)
Halogenation (p. 26-27) (8:01)
Halohydrin Formation (p. 28-30) (10:30)
Dihydroxylation (p. 31-33) (9:52)
Oxidative Cleavage & Ozonolysis (p. 34-35) (8:11)
How to Predict Products of Addition Reactions (p. 36-39) (15:49)
Synthesis with Substitution, Elimination, & Addition Reactions (p. 40-49) (26:00)
Reactions of Dienes & Electrophilic Addition (p. 50-53) (16:55)

Alkenes & Addition Reactions — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Naming Alkenes Practice Exam Solutions (3:18)
Predicting Products Practice Exam Solutions (26:30)
Mechanisms Practice Exam Solutions (7:57)
Identifying Reagents Practice Exam Solutions (8:55)
Synthesis Problems Practice Exam Solutions (27:07)

Alkynes — Topic Review (⏱️ <68 min)

Study Guide (fill this in as you watch the videos!)
Naming & Properties of Alkynes (p. 3-5) (6:24)
Acidity of Terminal Alkynes (p. 6-7) (7:32)
Reactions that Produce Alkynes (p. 8-9) (9:19)
Reduction & Hydrogenation of Alkynes (p. 10-11) (4:45)
Hydrohalogenation of Alkynes (p. 12-13) (3:53)
Hydration of Alkynes & Tautomerization (p. 14-18) (11:07)
Halogenation of Alkynes (p. 19) (2:33)
Ozonolysis of Alkynes (p. 20) (3:09)
Alkylation of Terminal Alkynes (p. 21-22) (8:07)
Synthesis Involving Alkynes (p. 23-25) (11:02)

Alkynes — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Naming Alkynes Practice Exam Solutions (2:52)
Predicting Products Practice Exam Solutions (12:22)
Mechanisms Practice Exam Solutions (5:09)
Identifying Reagents Practice Exam Solutions (5:05)
Synthesis Problems Practice Exam Solutions (24:06)

Radical Reactions — Topic Review (⏱️ <69 min)

Study Guide (fill this in as you watch the videos!)
Radicals Geometry & Resonance (p. 3-4) (5:35)
Main Patterns of Radical Mechanisms (p. 5-6) (5:52)
Methane Chlorination (p. 7-9) (9:56)
Selectivity & Thermodynamics of Radical Halogenation (p. 10-12) (10:30)
Radical Halogenation & Stereochemistry (p. 13-14) (6:13)
Allylic Bromination (p. 15-17) (12:17)
Autooxidation & Antioxidants (p. 18-20) (6:56)
Mechanism for Radical/Anti-Markovnikov Addition (p. 21-22) (4:31)
Synthesis & Radical Halogenation (p. 23-24) (6:24)

Radical Reactions — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Resonance & Intermediates Practice Exam Solutions (5:07)
Predicting Products Practice Exam Solutions (12:15)
Mechanisms Practice Exam Solutions (8:47)

Synthesis Strategies for Alkyl Halides, Alkenes, & Alkynes — Topic Review (⏱️ <77 min)

Study Guide (fill this in as you watch the videos!)
One-Step Syntheses & How to Memorize All These Reactions (p. 3-8) (12:56)
Transforming Functional Groups (p. 9-13) (17:14)
Changing the Carbon Skeleton (p. 14-15) (13:01)
Roadmap for Multi-Step Synthesis Problems (p. 16-21) (33:23)

Synthesis Strategies for Alkyl Halides, Alkenes, & Alkynes — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
One-Step Syntheses Practice Exam Solutions (9:29)
Multi-Step Syntheses Practice Exam Solutions (48:41)

Alcohols & Phenols — Topic Review (⏱️ <112 min)

Study Guide (fill this in as you watch the videos!)
Properties of Alcohols & Naming (p. 3-7) (8:43)
Alcohol & Phenol Acidity (p. 8-10) (8:57)
Preparing Alcohols via Substitution & Addition (p. 11-12) (10:01)
Diols (p. 18-19) (2:15)
Preparing Alcohols via Reduction (p. 13-17) (13:52)
Preparing Alcohols with Grignard Reagents (p. 20-22) (14:24)
Alcohols & Protecting Groups (p. 23-25) (10:17)
Substitution & Elimination Reactions with Alcohols (p. 26-29) (15:14)
Oxidation Reactions with Alcohols & Phenols (p. 30-37) (11:58)
Synthesis Involving Alcohols (p. 38-46) (16:04)

Alcohols & Phenols — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Naming Alcohols & Phenols Practice Exam Questions (7:27)
Predicting Products Practice Exam Questions (23:20)
Mechanisms Practice Exam Questions (11:37)
Synthesis Practice Exam Questions (32:08)

Ethers, Epoxides, Thiols, & Sulfides — Topic Review (⏱️ <97 min)

Study Guide (fill this in as you watch the videos!)
Naming & Properties of Ethers (p. 3-5) (7:58)
Crown Ethers (p. 6-7) (3:51)
Preparing Ethers (p. 8-11) (9:29)
Ether Reactions (p. 12-13) (4:42)
Naming & Properties of Epoxides (p. 14-15) (5:54)
Preparing Epoxides (p. 16-18) (4:46)
Enantioselective Epoxidation (p. 19-20) (4:46)
Ring-Opening Reactions of Epoxides (p. 21-25) (21:45)
Naming & Properties of Thiols & Sulfides (p. 26-27) (3:49)
Reactions of Thiols & Sulfides (p. 28-32) (10:23)
Synthesis Involving Epoxides (p. 33-43) (19:13)

Ethers, Epoxides, Thiols, & Sulfides — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Naming Ethers, Epoxides, Thiols, & Sulfides Practice Exam Questions (8:22)
Predicting Products of Ethers & Epoxides Reactions Practice Exam Questions (11:28)
Predicting Products of Thiols & Sulfides Reactions Practice Exam Questions (4:21)
Mechanisms Practice Exam Questions (10:33)
Synthesis Practice Exam Questions (19:53)

Infrared (IR) — Topic Review (⏱️ <66 min)

Study Guide (fill this in as you watch the videos!)
How Light, Matter, & Spectroscopy Work (p. 1-4) (9:45)
Key Parts of an IR Absorbance Spectrum (p. 5-6) (5:27)
How to Interpret Wavenumber (p. 7-12) (19:12)
How to Interpret Intensity & Percent Transmittance (p. 13-14) (5:25)
How to Interpret Shape (p. 15-20) (17:06)
Putting It All Together to Analyze an IR Spectrum (p. 21-23) (8:23)

Infrared (IR) Spectroscopy — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Analyzing Compounds & IR Spectra Practice Exam Solutions (34:06)
Distinguishing Between Two Compounds in a Reaction Practice Exam Solutions (14:46)

Mass Spectrometry — Topic Review (⏱️ <56 min)

Study Guide (fill this in as you watch the videos!)
Mass Spectrometry Overview (p. 3-5) (7:49)
Analyzing a Mass Spectrum (p. 6-11) (25:19)
How to Analyze Fragments in a Mass Spectrum (p. 12-15) (11:04)
Degrees of Unsaturation & Molecular Formulas (p. 16-18) (11:36)

Mass Spectrometry — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Analyzing a Mass Spectrum Practice Exam Solutions (36:05)
Calculating Degree of Unsaturation Practice Exam Solutions (15:02)

Nuclear Magnetic Resonance (NMR) Spectroscopy — Topic Review (⏱️ <127 min)

Study Guide (fill this in as you watch the videos!)
NMR Overview (p. 3-4) (6:08)
Number of Signals in a 1H NMR Spectrum (p. 5-9) (19:01)
Chemical Shift & Signal Location (p. 10-15) (23:42)
Integration & Area Under a Signal (p. 16-17) (7:40)
Shape, Multiplicity, & Coupling (p. 18-24) (18:57)
How to Draw the Expected 1H NMR Spectrum (p. 25) (10:52)
How to Analyze a 1H NMR Spectrum (p. 26-28) (25:30)
13C NMR Spectra (p. 29-31) (15:10)

Nuclear Magnetic Resonance (NMR) Spectroscopy — Practice Exam Questions

Practice Exam Questions
Practice Exam Questions Answer Key
Classifying Types of Protons Practice Exam Solutions (10:22)
Predicting Chemical Shift Practice Exam Solutions (16:47)
Integration Practice Exam Solutions (7:37)
Shape, Multiplicity, & Coupling Practice Exam Solutions (6:16)
Drawing the Expected 1H NMR Spectrum Practice Exam Solutions (12:07)
Analyzing NMR Spectra Practice Exam Solutions (31:41)
13C NMR Spectra Practice Exam Solutions (12:52)

How to Draw the Expected 1H NMR Spectrum (p. 25)

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