Chem 51C: Organic Chemistry III

Video Lectures

Displaying all 19 video lectures.
Lecture 1
Introduction to Carboxylic Acids.
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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
Reactivity of Carbonyl Compounds.
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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
Reactions of Organometallic Reagents.
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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
Reactions and Protecting Groups.
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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
Aldehydes and Ketones: Reactions.
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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
Formation of Imines & Enamines from Aldehydes & Ketones.
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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
Acid-Catalyzed Formation of Hydrates, Hemiacetals, & Acetals.
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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
The Chemistry of the Carboxylic Acid Family.
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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
Reactions of Carboxylic Acids, Esters, Amides, & Nitriles.
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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
Enols and Enolates.
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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
More Reactions of Enols and Enolates.
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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
The Aldol Reaction and the Michael Reaction.
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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
The Robinson Annulation and the Claisen Reaction.
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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
Introduction to Amines: Properties and Synthesis.
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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
Hofmann Degradation, Diazotization, & Aryl Diazonium Salts.
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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
Introduction to Carbohydrates: Structure and Stereochemistry
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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
More Structure, Stereochemistry, & Reactions of Carbohydrates.
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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
Amino Acids, Peptides, and Proteins.
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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
Organometallic Reactions in Organic Synthesis.
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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