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Chem 51C: Organic Chemistry III

Video Lectures

Displaying all 19 video lectures.

Lecture 1 Play Video	Introduction to Carboxylic Acids. Recorded on April 3, 2012 Index of Topics: -0:26 Office Hours -1:42 Textbook -4:57 Homework -13:22 Quizzes -15:21 Academic Honesty -16:52 Enrollment -17:05 Tutoring -18:02 Software -21:36 Carbonyl Chemistry -23:34 Amines, Sugars, and Selected Topics -25:08 Carboxylic Acids -32:52 Carbonyl Compounds -42:07 Some Properties of Carboxylic Acids -49:04 IR of Carboxylic Acids -55:31 NMR of Carboxylic Acids -59:55 Oxidation of Alcohols -1:03:22 Oxidation of Aromatic Compounds -1:05:55 Carboxylate Anions -1:08:54 pKa of Carboxylic Acids -1:13:06 Equilibria in Acid-Base Reaction -1:15:41 Inductive Stabilization of Conjugate Base
Lecture 2 Play Video	Reactivity of Carbonyl Compounds. Recorded on April 5, 2012 Index of Topics: -1:00 Reactivity with Nucleophilic -4:08 Resonance in a Carbonyl group -8:41 Nucleophiles and Carbonyls -18:09 LiAlH4 and NaBH4 -26:29 Example Reaction -32:38 Reduction -44:10 Hydride Reducing Agents -48:57 Sodium Hydride -54:02 Oxidation State -1:00:14 Reactivity Toward Nucleophiles -1:08:44 Making Racemic Mixtures -1:12:38 Chiral Hydride Reagent -1:16:05 Tert-Butyl Cyclohexanone Example
Lecture 3 Play Video	Reactions of Organometallic Reagents. Recorded on April 12, 2012 Index of Topics: -1:36 Ketone/Aldehyde Reduction -5:56 Grignard Reagents -12:31 Polarity of Grignard Reagent -16:01 Basicity of Grignard Reagent -19:22 Grignard Reagents and Water/Alcohol -21:32 Organolithium Reagent -25:50 Acetylide Anions -34:07 Making Acetylide Anion -38:29 Reactivity of the Carboxylic Acid Family -44:56 Addition-Elimination Reaction -48:12 Examples of Carboxylic Acid Reduction -53:29 Multiple Additions onto Carboxylic Acids -59:50 Leaving Groups -1:08:27 Synthesizing Example -1:16:54 More Examples of Synthesizing
Lecture 4 Play Video	Reactions and Protecting Groups. Recorded on April 12, 2012 Index of Topics: -3:09 Carboxylic Acids and LiAlH4 -9:07 DIBAL-H -14:59 Multiple Equivalents of Organometallic Reagents -18:18 Organocuprate Reagent -22:11 Chemoselectivity -26:14 Reducing Carbonyls and Alkenes -30:48 Oxidizing Agents -33:31 Regioselectivity -36:10 Resonance -40:00 Enones and Nucleophiles -41:45 Enolate Anion -44:15 Tautomerization -45:53 Protecting Groups -50:40 Taking the Protecting Groups Off -56:32 Synthesizing -1:05:33 Corrections
Lecture 5 Play Video	Aldehydes and Ketones: Reactions. Recorded on April 17, 2012 Index of Topics: 1:08-Carbonyls and Strongly Basic Nucleophiles 4:01-Weakly Basic Nucleophiles 9:56-Naming Carbonyls 14:22-Properties of Ketones and Aldehydes 16:59-Reactivity 19:38-IR Spectroscopy 26:04-Conjugation 32:12-NMR 37:52-Synthesis of Aldehydes and Ketones 47:14-Reactions with Nucleophiles 54:25-Acetylene and Hydrogen Cyanide Examples 1:00:16-Workup of Cyanide Anion Addition 1:04:15-Wittig Reaction 1:09:44-Wittig Reaction Mechanism 1:16:24-Making a Wittig Reagent 1:18:14-Wittig Reaction Examples 1:20:11-Stereoselectivity
Lecture 6 Play Video	Formation of Imines & Enamines from Aldehydes & Ketones. Recorded on April 19, 2012 Index of Topics: 4:10-HCN Addition and Wittig Reaction 7:13-Ketones or Aldehydes and Amines 10:32-Aldimine Formation Example 15:23-Ketimine Formation Example 19:55-Mechanism of Acid-Catalyzed Imine Formation 33:28-Acid-Catalyzed Breakdown of the Hemiaminal 44:33-Answer to Student Question 47:50-Imine Formation 49:49-Reversibility 53:15-Example of Reversibility 55:50-Enanamines 59:04-Nucleophilicity of Amine 1:01:50-Imine Reaction with Base
Lecture 7 Play Video	Acid-Catalyzed Formation of Hydrates, Hemiacetals, & Acetals. Recorded on April 24, 2012 Index of Topics: 1:19-Electrophilicity of Aldehydes and Ketones 5:37-Hydrates 12:17-Acid-Catalyzed Addition of Water to Acetone 21:29-Acetone Enol Example 24:01-Reverse Reaction 25:31-Energy Diagram 29:28-Reverse Reaction Mechanism 36:38-Acid-Catalyzed Acetal Formation 40:00-Hemiacetal 43:01-Strong Acid 47:23-Hemiacetal Formation Mechanism 50:52-Hemiacetal to Acetal Mechanism 1:00:52-Acid-Catalyzed Acetal Hydrolysis 1:06:12-Protecting Groups 1:12:15-Cyclic Hemiacetal
Lecture 8 Play Video	The Chemistry of the Carboxylic Acid Family. Recorded on April 26, 2012 Index of Topics: 2:00-Carboxylic Acid Derivatives 5:54-Nomenclature 17:44-Acid Chlorides and Anhydrides 22:28-Boiling Points of Esters Versus Alkanes 26:22-Resonance Structures 28:59-Properties of Amides 35:12-IR Spectroscopy 43:51-Reaction of Acid Chloride and Anhydride in Water 45:05-Reaction of Esters and Amides in Water 51:58-NMR of Carbonyls 54:51-Carboxylic Acid Derivatives and Nucleophiles 58:08-Weakly Basic Nucleophiles 1:00:49-Balanced Equation Example 1:05:19-Student Question 1:09:28-Acid Chloride Reaction Example 1:14:11-Relative Reactivity of Carboxylic Acid Derivatives 1:17:44-Anhydride Reaction
Lecture 9 Play Video	Reactions of Carboxylic Acids, Esters, Amides, & Nitriles. Recorded on May 1, 2012 Index of Topics: 0:56-Esters and Carboxylic Acids Reactivity 9:29-Fischer Esterification 16:41-Fischer Esterification Mechanism 29:52-Hydrolysis of Esters 32:13-Saporification 37:27-Amides and Nitriles 53:36-Making Acid Chlorides 58:11-Making Amides 1:01:33-Nitriles and LiAlH4 and other Organometallic Reagents
Lecture 10 Play Video	Enols and Enolates. Recorded on May 3, 2012 Index of Topics: 1:16-Reactivity of Ketones 3:02-Enols 6:36-Enolate Anion 9:47-Enolates and Electrophiles 16:49-Equilibrium Between Tautomers 23:07-Acid-Catalyzed Enol Formation 29:18-Energy Diagram 37:51-Multiple Additions 46:41-pKa of Alpha Protons 53:05-Base-Catalyzed Enol Formation 58:56-Stereochemistry 1:03:42-LDA 1:11:28-Kinetic Product vs Thermodynamic Product 1:17:56-LDA and Stereochemistry
Lecture 11 Play Video	More Reactions of Enols and Enolates. Recorded on May 10, 2012 Index of Topics: 1:05-Enolates 3:57-Enolates and Electrophiles 9:11-Alpha-Halogenation of Ketones and Aldehydes 13:58-Halogenation Mechanism 21:58-Halogenation Example 25:10-Alpha-Halogenation Promoted by Base 35:29-Haloform Reaction 39:02-Haloform Reaction Mechanism 43:37-pKa Values 53:20-Reason for Acidity 1:00:35-AcetoAcetic Ester Synthesis 1:10:36-Malonic Ester Synthesis 1:14:44-Example Problem
Lecture 12 Play Video	The Aldol Reaction and the Michael Reaction. Recorded on May 15, 2012 Index of Topics: 1:28-Enolate Formation 3:56-Aldol Reaction 11:44-Retrosynthesis Example 18:40-Original Aldol 21:32-Aldol Mechanism 26:45-Features of Aldol Mechanism 35:25-Aldol Example 38:21-Synthesis Example 43:16-Stereochemistry 46:46-Crossed Aldol Reaction 52:48-Intramolecular Aldol Reaction 1:01:10-Retrosynthesis of Intramolecular Aldol Reaction 1:03:16-The Michael Reaction 1:05:34-Resonance Structures 1:08:27-Strongly Basic Nucleophiles 1:12:52-Michael Reaction Mechanism 1:16:35-Retrosynthesis Example
Lecture 13 Play Video	The Robinson Annulation and the Claisen Reaction. Recorded on May 17, 2012 Index of Topics: 1:40-Michael Reaction 4:19-Aldol Reaction 5:54-Aldol Reaction with Dehydration 8:32-The Robinson Annulation 13:13-Reactions Involved in Robinson Annulation 26:15-Robinson Annulation Example 28:11-Retrosynthesis Example 33:55-Synthesizing Examples 39:55-Other Conditions 41:11-Acid-Catalyzed Michael Reaction 43:30-Acid-Catalyzed Aldol Reaction 45:18-Example Problem 50:00-Claisen Reaction 53:21-Claisen Reaction Mechanism 57:59-Synthesis Example 1:04:27-Crossed Claisen Reaction 1:08:46-Retro-Claisen Reaction Mechanism 1:11:04-Dieckmann Reaction 1:17:41-Synthesis Example
Lecture 14 Play Video	Introduction to Amines: Properties and Synthesis. Recorded on May 22, 2012 Index of Topics: 5:49-Morphine and Cocaine 15:32-Amines 22:06-Basicity 29:02-pKa and Hybridization 36:14-Physical Properties 42:12-IR Spectrum 44:28-NMR 48:18-Amine Synthesis 52:11-Carbonyl vs Imine 53:52-Reductive Amination 55:06-Sodium Cyanoborohydride 59:46-Alkylating Nitrogen 1:02:19-Gabriel Synthesis of Primary Amines
Lecture 15 Play Video	Hofmann Degradation, Diazotization, & Aryl Diazonium Salts. Recorded on May 24, 2012 Index of Topics: 2:13-Alkylation 10:19-Hofmann Degredation 14:56-Silver Oxide and Water 16:43-Hofmann Elimination 17:18-E2 Elimination 24:29-Conventional E2 Elimination 26:47-Elimination Example 31:29-2-bromobutane Example 36:39-Aromatic Chemistry 40:21-Diazotization Reaction 52:12-Diazonium Ion Reactivity 55:29-Dizonium Salt Reactions 1:05:05-Synthesis Examples 1:18:27-Alkyl Diazonium Salts are Unstable 1:19:53-Nitrosamines
Lecture 16 Play Video	Introduction to Carbohydrates: Structure and Stereochemistry Recorded on May 29, 2012 Index of Topics: 3:12-Carbohydrates 8:39-Lactose 12:47-Subunits of Lactose 15:38-Alpha-D-Glucose 18:04-Anomers 21:51-Interconversion of Glucose Anomers 25:29-Interconverting Lactose? 28:26-Forms of Galactose 32:15-Optical Rotation 37:25-Chair Representation of Glucose 39:11-Haworth Representation of Glucose 42:40-Open Form Representation of Glucose 46:56-Fischer Projection 51:15-Converting Haworth Projection to a Fischer Projection 53:48-PyMOL Demonstration 1:02:49-Using Fischer Projections to Make Different Sugar Molecules 1:04:32-8 D Sugars
Lecture 17 Play Video	More Structure, Stereochemistry, & Reactions of Carbohydrates. Description: This is the third quarter course in the organic chemistry series. Topics covered include: Fundamental concepts relating to carbon compounds with emphasis on structural theory and the nature of chemical bonding, stereochemistry, reaction mechanisms, and spectroscopic, physical, and chemical properties of the principal classes of carbon compounds. Organic Chemistry 51C is part of OpenChem. http://learn.uci.edu/openchem Recorded on May 31, 2012 Index of Topics: 1:40-Aldotetroses 9:16-Aldopentoses 11:40-Ribose 18:02-Ketoses 22:47-Hydrolysis of Glycosides 36:34-Formation of Glycosides 43:51-Alcohol Groups in Sugars 48:05-Making Esters 51:03-Reactions of Aldo Sugars 55:32-Sugar Structure Determination 59:12-Reducing Sugars 1:00:07-Tollen's Test 1:05:26-Which Aldotetrose? 1:15:24-Kiliani-Fischer Synthesis
Lecture 18 Play Video	Amino Acids, Peptides, and Proteins. Recorded on June 6, 2012 Index of Topics: 2:49-Amino Acid Structure 5:55-Examples of Polypeptides 12:18-20 Common Amino Acids 17:03-Polar & Charged Amino Acids 22:35-Chemical Synthesis of Peptides and Proteins 27:49-Protecting Groups 31:54-DCC 40:07-Boch Deprotection Mechanism 42:44-Special Amino Acids 43:33-Additional Protecting Groups 46:42-Modern Solid-Phase Peptide Synthesis 54:20-Boch Opolystyrene Example 59:54-Fmoc Group
Lecture 19 Play Video	Organometallic Reactions in Organic Synthesis. Recorded on June 7, 2012 Index of Topics: 3:52-Grignard Reagent 7:01-Organometallic Complex 12:47-Organocopper Reagents 23:05-Organocuprate Mechanism 25:17-Stereospecificity 32:02-Drawbacks of Copper Chemistry 33:55-Suzuki Reaction 42:48-3 Main Steps to the Suzuki Mechanism 55:37-Using the Suzuki Reaction in Organic Synthesis 1:03:00-Olefin Metathesis 1:11:16-Partner Swapping Mechanism 1:15:20-Ring-Closing Metathesis