Chem 51B: Organic Chemistry II
Video Lectures
Displaying all 26 video lectures.
Lecture 1![]() Play Video |
Review of Chem 51A Recorded on January 7, 2013. Index of Topics: 00:44- Why invest in organic chemistry? 03:40- Are there other reasons to invest in organic chemistry? 04:53- Why invest in this course? 06:38- Who is running this course? 07:34- Who are the Sherpas? 08:56- What are we covering this quarter? 11:06- Where is my syllabus? 11:36- How is my grade determined? 14:13- Sapling Online Homework 15:52- Why go to discussion section? 17:35-Organic Chemistry Department Tutoring 18:17- What other resources are available? 20:33- Are more structured resources available? LARC 21:42- How do I communicate with the instructor? 23:39- Notable words from Benjamin Franklin 25:45- Review of Chem 1A 29:10- Chapter 1- Structure and Bonding 34:43- Chapter 7/8- Review of primary and secondary Alkyl Halides |
Lecture 2![]() Play Video |
Alcohols, Ethers, and Epoxides - Part 1 Lec 02. Organic Chemistry -- Alcohols, Ethers, and Epoxides -- Part 1 Recorded on January 9, 2013. Index of Topics: 00:17- First new drug in 40 years approved by FDA 01:17- Structure of bedaquiline 2:23- EEE website CHAPTER 7/8 4:37- Reactions of primary and secondary Alkyl Halides 6:54- Reactions of tertiary Alkyl Halides 12:14- Examples 20:58- Examples (slide 2) CHAPTER 9-Alcohols, Ethers, and Epoxides 28:14- 9.1: Introduction 36:46- 9.2: Structure 39:35- 9.3: IUPAC Nomenclature |
Lecture 3![]() Play Video |
Alcohols, Ethers, and Epoxides - Part 2 Lec 03. Organic Chemistry -- Alcohols, Ethers, and Epoxides -- Part 2 Recorded on January 11, 2013. Index of Topics: 00:17- Student's Choice 01:41- 9.3: IUPAC Nomenclature 04:47- 9.4: Properties 9:51- 9.5: Cool Examples 14:18- 9.6: Alkoxides As Nucleophiles 22:00- 9.6: Make alkoxides with sodium hydride 29:32- 9.6: Strategic ether synthesis 37:16- 9.7: Don't displace HO- or RO- in Sn2 43:49- 9.8: E1 Dehydration of tertiary Alcohols via Carbocations |
Lecture 4![]() Play Video |
Alcohols, Ethers, and Epoxides - Part 3 Lec 04. Organic Chemistry -- Alcohols, Ethers, Epoxides -- Part 3 Recorded on January 14, 2013. Index of Topics: 00:17- OLED TV 01:38- OLED explained 03:34- 9.8: E1 Dehydration of tertiary Alcohols via Carbocations 07:00- 9.8: E1 Dehydration of secondary Alcohols via Carbocations 10:28- 9.9: Carbocations rearrange through 1,2 shifts 18:38- 9.9: 1,2 shifts make challenging test questions 26:09- 9.10: Dehydration with POCl3/pyridine 33:35- 9.11: SN1 conversion of tertiary R-OH to tertiary R-X 40:00- 9.11: SN2 conversion of primary R-OH to primary R-Cl with ZnCl2 45:29- 9.12A: Sn2 conversion of R-OH to R-Cl with SOCl2 |
Lecture 5![]() Play Video |
Alcohols, Ethers, and Epoxides Part 4. Lec 05. Organic Chemistry -- Alcohols, Ethers, and Epoxides -- Part 4 Recorded on January 16, 2013. Index of Topics: 00:18- Chemical leak into river puts focus on plant 00:53- Structure of Aniline 02:35- 9.12A: SN2 conversion of R-OH to R-Cl with SOCl2 4:03- 9.12B: SN2 conversion of R-OH to R-Br with PBr3 08:51- 9.12C: Why make alkyl halides? 14:57- 9.13: Convert R-O-H to R-O-Ts 22:16- 9.14: Reactions with Ethers with Hl and HBr 28:29- 9.15A: SN2 Reactions of Epoxides Under Basic Conditions 33:29- 9.15A: Reactions of Epoxides Under Basic Conditions 36:00- 9.15B: SN2 Reactions of Epoxides Under Acidic Conditions 41:46- 9.15B: 3-Membreed ring "onium" ions = strange regioselectivity |
Lecture 6![]() Play Video |
Alkenes, Part 1. Lec 06. Organic Chemistry -- Alkenes -- Part 1 Recorded on January 18, 2013. Index of Topics: 00:22- Exterminators use rain-activated chemical to wash away bugs 01:54- Structure of bifenthrin 06:56- How to enumerate steps CHAPTER 10-Alkenes 09:37- 10.1:Introduction 10:51- 10.1: Introduction-Configurational stability of C=C vs. C-C 13:47- 10.1: Introduction-Contrast reactivity of C-C vs. C=C 16:59- 10.1: Degree of Unsaturation 20:40- 10.2: Calulate Degrees of Unsaturation from Molecular Formula 29:20- 10.3: Know cis/trans & E/Z 37:58- 10.4.5.6: Physical Properties, Interesting Alkenes, Lipids 42:48- 10.7: Ways I Like to Make Alkenes (so far) |
Lecture 7![]() Play Video |
Alkenes, Part 2. Lec 07. Organic Chemistry -- Alkenes -- Part 2 Recorded on January 23, 2013. Index of Topics: 00:16- Resvology Debuts Anti-Aging Skin Care Line with Gene-Activating Molecule 00:54- 4-AR molecule 04:18- 10.8: Addition of Electrophiles to Alkenes 14:03- 10.8: Syn and Anti Relationships 19:09- 10.9: Addition of H-X: Hydrohalogenation 23:56- 10.9: Watch for Rearrangements of Carbocations 33:39- 10.10: Markovnikov's Rule: Add H to less-substituted carbon 38:18- 10.10: Markovnikov's Rule is Based on Carbocation Stability 42:57- 10.11: No control in formation of stereogenic centers 46:53- 10.11: No control in formation of stereogenic centers, slide 2 |
Lecture 8![]() Play Video |
Alkenes, Part 3. Lec 08. Organic Chemistry -- Alkenes -- Part 3 Recorded on January 25, 2013. Index of Topics: 00:07- Foul smell complaints in southern England after gas leak 00:51- Mercaptans stink 02:23- The Lubrizol plant map 04:03- 10.8: Addition of Electrophiles to Alkenes 5:44- 10.12: Hydration: Acid-Catalyzed Addition of H2O 09:49- 0.12: Hydration: Acid-Catalyzed Addition of H20 15:30- 10.13: Halogenation: Addition of Br2 and Cl2 18:26- 10.13: Mechanism Involves a 3-Membered Ring Halonium Ion 25:28- 10.14: Stereochemistry of Halogenation 30:44- 10.14: Halogenation Stereochemistry 36:08- 10.15: Halohydrin Formation: Halogenation in Water 40:54- 10.15: Halohydrin Formation: Halogenation in Water-Steps |
Lecture 9![]() Play Video |
Alkynes, Part 1. Lec 09. Organic Chemistry -- Alkynes -- Part 1 Recorded on January 28, 2013. Index of Topics: 00:11- Why Europe's Healthiest Economy Has Its Worst Drug Problem 01:36- Morphine and Fentanyl 02:56- 10.8: Recall Addition of Electrophiles to Alkenes 06:46- 10.16: Hydroboration-Oxidation 10:47- 10.16: Hydroboration Step 16:58- 10.16B: Oxidation of the C-B Bond 21:16- 10.17, 10.18: Keeping Track, Alkenes in Synthesis 29:25- Multi-step synthesis CHAPTER 11-Alkynes 33:49- 11.1: Introduction 38:09- 11.1: Reactivity |
Lecture 10![]() Play Video |
Alkynes, Part 2. Lec 10. Organic Chemistry -- Alkynes -- Part 2 Recorded on January 30, 2013. Index of Topics: 00:10- Gatorade to remove controversial ingredient 02:36- Soybean oil vs. brominated vegetable oil 05:20- 11.2,11.3,11.4: Names, Properties, Examples 11:00- 11.5: Make Alkynes Through Dehydrohalogenation 16:48- 11.5: Super Basic Condns 22:29- 11.5: Make Alkynes Through Dehydrohalogenation 26:38- 11.6: Alkyne Reactivity 30:54- 11.6: Alkyne Reactivity, Slide 2 34:13- 11.7: Addition of HX to Alkynes 37:17- 11.7: Addition of HX to Alkynes, Slide 2 41:24- 11.7: Addition of HX to Vinyl Halides For more information and access to courses, lectures, and teaching material, please visit the official UC Irvine OpenCourseWare website at: http://ocw.uci.edu |
Lecture 11![]() Play Video |
Alkynes, Part 3. Lec 11. Organic Chemistry -- Alkynes -- Part 3 Recorded on February 4, 2013. Index of Topics: 00:29- A Perfect Red 02:42- Cochineal 05:07- 11.7: Best Alkynes for H-X Addition 11:49- 11.7: Worst Alkynes for H-X Addition 15:58- 11.8: Addition of Cl2 and Br2 to Alkynes 21:52- 11.8: Addition of Cl2 and Br2 to Alkynes-Add two equivalents of halogen to generate the tetrahalide 24:58- 11.9: Hydration: Addition of H2O 28:33- 11.9: Initial Product=enol 31:58- 11.9: Mechanism 37:38- 11.9: Keto-Enol Tautomerism |
Lecture 12![]() Play Video |
Alkynes, Part 4. Lec 12. Organic Chemistry -- Alkynes -- Part 4 Recorded February 6, 2013. Index of Topics: 00:09- Beer molecule discovery bolsters Seattle biotech upstart 00:59- Hops 02:52- Chapter 11-Key Reactions 08:58- 11.9: Acid-Catalyzed Tautomerism 09:23- 11.9: Initial product=enol 10:34- 11.10: Hydroboration-Oxidation of Alkynes 11:33- 11.9: Acid-Catalyzed Tautomerism 21:23- 11.10: Hydroboration-Oxidation of Alkynes 24:26- 11.10: Hydroboration-Oxidation of Alkynes, Slide 2 30:19- 11.11: Acetylide Anions-Pkas 36:12- 11.11: Acetylide Anions-can be used for SN2 reactions 42:04- 11.12-Synthesis |
Lecture 13![]() Play Video |
Reduction and Oxidation, Part 1. Lec 13. Organic Chemistry -- Reduction and Oxidation -- Part 1 Recorded on February 8, 2013. Index of Topics: 00:10- Imitation Vanilla 01:13- 'Vanilla Extract' produced in Mexico is no bargain 02:09- The Tonka Bean 03:30- Structure of Vanillin vs. Coumarin CHAPTER 12-Oxidation and Reduction 05:52- 12.1: Introduction 12:42- 12.2: Secret "Hydride" Reducing Agents from Ch 20 15:54- 12.2: Other Reducing Agents 19:20- 12.3,12.4: Hydrogenation of Alkenes 25:12- 12.3,12.4: Hydrogenation of Alkenes-Benzene rings, C=C bonds 29:37- 12.5A,B: Partial Hydrogenation of Alkynes 32:20- 12.5 A,B: Hydrogenation of Alkynes 37:17- 12.5C: Partial Hydrogenation of Alkynes to Alkenes 42:57- 12.5C: Dissolving metal reduction |
Lecture 14![]() Play Video |
Reduction and Oxidation, Part 2. Lec 14. Organic Chemistry -- Reduction and Oxidation -- Part 2 Recorded on February 11, 2013 Index of Topics: 00:09- Vanillin Stain 03:16- Various Dip Stains 06:53- 12.5C: Partial Hydrogenation of Alkynes to Alkenes 08:23- 12.5C: Dissolving metal reduction 13:58- 12.6: the Reductive Opening of Epoxides 19:00- 12.8: Epoxidation of C=C with mCPBA 23:28- 12.8: Epoxidation of C=C with mCPBA-stereospecific 25:59- 12.8: Epoxidation of C=C with m-CPBA-draw all substituents 28:06- 12.9A: Two-Step Anti-Dihydroxylation 31:51- 12.9B: Syn-Dihydroxylation 37:33- 12.9B: Syn-Dihydroxylation, Slide 2 |
Lecture 15![]() Play Video |
Reduction and Oxidation, Part 3. Lec 15. Organic Chemistry -- Reduction and Oxidation -- Part 3 Recorded on February 13, 2013. Index of Topics: 00:09- Canker sore drug helps mice lose weight 01:37- Amlexanoxx 04:00- 12.10: Ozonolysis of Alkenes with Ozone 10:24- 12.10: Oxidative Cleavage of Alkenes 18:22- 12.11: Oxidative Cleavage of Alkynes with Ozone 20:33- 12.12A, 12.12B: Chromium Oxidant Recipes 26:52- 21.12A, 12.12B: No Oxidation of Tertiary Alcohols 29:48- 12.12A, 12.12B: Oxidation of Secondary Alcohols to Ketones 32:32- 12.12A, 12.12B: Mechanism for Oxidation of Alcohols 40:30- 12.12A, 12.12B: Oxidation of Primary Alcohols 43:12- 12.12A, 12.12B: Why Primary Alcohols Oxidize to Carboxylic Acids in H20 46:48- 12.13: Green Chemistry, Ethanol 47:27- 12.15: Sharpless Epoxidation |
Lecture 16![]() Play Video |
Infrared Spectroscopy + Ch. 14. Lec 16. Organic Chemistry -- Infrared Spectroscopy and Chapter 14 Recorded February 15, 2013. Topics Covered: Infrared Spectroscopy and Chapter 14. Index of Topics: 00:09- Superomniphobic material 01:47- Underlying Molecules CHAPTER 13- Mass Spectrometry and Infrared Spectroscopy 04:42- 13.1: The Mass Spectrometer-how does it work? 09:26- 13.1-13.3: Mass spectra are complex due to fragmentation 11:55- 13.4: The Exact Mass gives the Molecular Formula 15:14- 10.2: Use the Molecular Formula to determine Degree of Unsaturation 19:25- 13.5: Electromagnetic Radiation and Infrared 22:45- 13.6: Dumb Characteristics of an IR spectrum 26:56- 13.6: Key Frequency Regions of the IR spectrum 32:22- 13.6: Practice: Regions of the IR spectrum 34:58- 13.6,7: Polar Bonds Lead to Intense Peaks 39:35- 13.7: Hydrogen bonding leads to lumpy peaks 42:06- 13.6: Dumb Characteristics of an IR spectrum (revisited) 42:44- 13.6,7: Check if C-H stretches are above or below 300 cm^(-1) 46:00- Reading Spectra Examples |
Lecture 17![]() Play Video |
NMR Spectroscopy. Lec 17. Organic Chemistry -- NMR Spectroscopy Recorded February 20, 2013. Index of Topics: 00:09- Mapping the human brain 01:34- Can we see Chemistry Inside the Brain? CHAPTER 14- Nuclear Magnetic Resonance Spectroscopy 05:52- 14.1: Which elements have magnetic resonance properties? 12:47- 14.1A: The NMR Spectrometer- A Superconducting Magnet 16:38- 14.1A: Energetic Differences Between Two Nuclear Spin States 19:39- The Sound of an NMR Spectrometer 21:03- 14.1: Why we perform H NMR and C NMR separately 23:10- 14.1A: The NMR Spectrometer- A Superconducting Magnet (revisited) 24:16- 14.1B: Strange Terms Because Every NMR Magnet is Different 31:32- 14.1A: C NMR is simpler than H NMR so use it first 34:56- 14.2: How many signals should I expect in the C spectrum? 43:40- 14.2: How many signals should I expect in the C spectrum, Slide 2 46:05- 14.2: Use Symmetry to Predict the Number of C Signals |
Lecture 18![]() Play Video |
NMR Spectroscopy, Part 2. Lec 18. Organic Chemistry -- NMR Spectroscopy -- Part 2 Recorded February 22, 2013. Index of Topics: 00:13- Hash Oil 01:25- Structure of tetrahydrocannaboil 04:02- 14.11, 14.12: C NMR Chemical Shift Ranges 11:20- 14.11, 14.12: Practice Using C NMR Chemical Shift Ranges 15:40- 14.2: How many signals should I expect in the H spectrum? 20:46- 14.2: Diastereotopic or Enantiotopic Protons? Use the Z-test 27:19- 14.2: Use the Z-test, Slide 2 29:58- 14.3B: H NMR Chemical Shift Ranges 39:27- 14.3A, 14.4: Shielding and Deshielding Effects-anisotropy 42:23- 14.3A, 14.4: Shielding and Deshielding Effects-proximity to the pi system 46:03- 14.3A, 14.4: Sheilding and Deshielding Effects-electronegative atoms 48:32- 14.5: Integration of H NMR Peaks |
Lecture 19![]() Play Video |
NMR Spectroscopy, Part 3. Lec 19. Organic Chemistry -- NMR Spectroscopy -- Part 3 Recorded February 25, 2013. Index of Topics: 00:38- The possibilities of 3D printing 01:02- 3D home printer 02:23- Meltable Polymers for Low-Cost 3D Printing 04:57- 14.6: Coupling between nuclei leads to splitting of peaks 11:28- 14.6A,B: Analysis of Doublet and Triplet Splitting Patterns 23:00- 14.6C: Splitting Rules 32:02- 14.6C: The n+1 Splitting Rule 39:35- Splitting Example #1 43:25- 14.7: Example-Two types of Protons 46:59- 14.8: Variations in the Magnitude of Splitting |
Lecture 20![]() Play Video |
Radicals. Lec 20. Organic Chemistry -- Radicals Recorded February 27. 2013. Index of Topics: 00:17- Pycnogenol 00:42- What is Pycnogenol? 01:11- Molecular Structure of Pycnogenol 03:22- 14.8: Splitting by More than One Type of Proton 07:55- 14.9: Time Dependence of H NMR Spectroscopy-Bond Rotation 09:42- 14.9: Time Dependence of H NMR Spectroscopy CHAPTER 15- Radicals 15:37- 15.1: Radicals-Reactivity and Stability 21:04- 15.1, 15.2: Reactions of Radicals-a specialized arrow symbol 24:55- 15.3, 15.6, 15.7: Selective conversion of tertiary R-H to tertiary R-Br 29:35- 15.4: Mechanism for Radical Bromination 36:26- 15.8: Carbon radicals react on either end of the p orbital 42:15- 15.10: Allylic Bromination 48:06- 15.13: Anti-Markovinkov of HBr to H2C=CHR 50:39- Chapter 15-Radical Summary |
Lecture 21![]() Play Video |
Conjugation, Resonance, Diels-Alder Reactions, Part 1. Lec 21. Organic Chemistry -- Conjugation, Resonance, Diels-Alder Reactions -- Part 1 Recorded March 4, 2013. Index of Topics: 00:31- Doritos Ingredients 01:38- Molecular Structures of Doritos Ingredients CHAPTER 16-Conjugation, Resonance, and Dienes 03:46- 16.1: What is Conjugation? 10:36- 16.3: Common Forms of Resonance 20:07- 16.3, 16.4: Rank Resonance Structures to Predict Properties 29:00- 16.5: Lone pairs must be in p orbitals to interact with pi bonds 35:27- 16.6: Two flat conformers of conjugated dienes 41:12- 16.9: Reactivity of pi bonds vs. stability of the overall molecule 46:06- 16.10-1,2: Addition vs. 1,4-Addition |
Lecture 22![]() Play Video |
Conjugation, Resonance, Diels-Alder Reactions, Part 2. Lec 22. Organic Chemistry -- Conjugation, Resonance, Diels-Alder Reactions -- Part 2 Recorded March 6, 2013. Index of Topics: 00:13- A molecule today, a barrel tomorrow 00:42- Fracking 04:57- 16.12: The Diels-Alder Reaction 10:42- 16.13: Diene Requires an s-cis conformation 14:53- 16.13: Stereospecificity in the Diels-Alder Reaction 21:08- 16.13: Drawing Bridged Bicyclic Products of Diels-Alder Reactions 29:41- 16.13: The Endo Rule for Cyclic Dienes CHAPTER 17-Benzene and Aromatic Compounds 34:05- 17.1: The C=C pi bonds in benzene exhibit low reactivity 39:19- 17.3: Disubstituted benzene rings: ortho, meta, and para relationships 45:06- 17.4: C NMR Spectroscopy 47:14- 17.4: H NMR Spectroscopy |
Lecture 23![]() Play Video |
Aromaticity. Lec 23. Organic Chemistry -- Aromaticity Recorded on March 8, 2013. Index of Topics: 00:11- Lake Elsinore toddler bitten by rattlesnake 00:54- Antivenom 05:00- 16.13: Drawing Bridged Bicyclic Products of Diels-Alder Reactions (corrected slide) 06:25- 17.7: Huckel's Rule-Recognizing Anti-aromatic Compounds 12:43- 17.7: Recognizing Anti-aromatic Compounds 18:13- 17.8C: How Do I Know if an atom is planar? 19:05- 17.8C: Aromatic Ions 26:29- 17.8C: How Do I Know if an atom is planar, revisited 29:56- 17.8D: Aromatic Heterocycles-Which lone pairs do I count? 38:45- 17.8B: Other Aromatic Compounds |
Lecture 24![]() Play Video |
Electrophilic Aromatic Substitution. Lec 24. Organic Chemistry -- Electrophilic Aromatic Substitution -- Part 1 Recorded on March 11, 2013. Index of Topics: 00:36- Natural Does Not Mean Safe 01:43- Molecular structure of allantoin CHAPTER 18-Electrophilic Aromatic Substitution=E.A.S. 04:00- Chapter 18 Introduction 08:51- 18.1: Five Important Electrophilic Aromatic Substitution Reactions 14:39- 18.2: Two-Step Mechanism for E.A.S. 22:33- 18.3: Dalogenation with FeX3 and X2 31:05- 18.4: Nitration with HNO3 and H2S04 39:48- 18.4: Sulfation with SO3 and H2SO4 45:56- 18.5: Friedel-Crafts Acylation with RCOCl and AlCl3 |
Lecture 25![]() Play Video |
Electrophilic Aromatic Substitution Part 2. Lec 25. Organic Chemistry -- Electrophilic Aromatic Substitution -- Part 2 Recorded March 13, 2013. Index of Topics: 00:10- Red Tide Kills Record Number of Manatees 01:02- Molecular structure of brevetoxin A 02:56- 18.1: Five Important Electrophilic Aromatic Substitution Reactions 04:21- 18.5: Friedel-Crafts Alkylation with AlCl3 and Alkyl halides 09:37- 18.5: Friedel Crafts Alkylation without 14:32- 18.6, 18.7, 18.8: Substituents Affect Rates and Regiochemistry in E.A.S. 20:43- 18.9: Compare Arenium Ions to Explain Regiochemistry 26:41- 18.6: Substituents that favor ortho, para substitution 31:13- 18.6: Substituents that favor meta substitution 35:56- 18.6: L.P. Resonance Donor Effects Outcompete Inductive Effects 40:32- 18.7: Summary of EAS Substituent Effects-Know This Summary 45:43- 18.10: Special Rules for Friedel-Crafts Reactions 46:33- 18.9: Don't Confuse the directing group with the new substituent 49:58- 18.10: Special Rules fro Friedel-Crafts Reactions (revisited) |
Lecture 26![]() Play Video |
Electrophilic Aromatic Substitution, Part 3. Lec 26. Organic Chemistry -- Electrophilic Aromatic Substitution -- Part 3 Recorded on March 15, 2013 Index of Topics: 00:10- Removing Toxic Chemicals with POPs 00:43- Molecular Structures of POPs 04:02- Summary of EAS Substituent Effects: Know This Summary 07:41- 18.9: Over-Activated Anilines and Phenols 11:56- 18.11: EAS on Disubstituted Benzene Rings 15:58- 18.11: EAS on Disubsituted Benzene Rings-no substitution between meta-substituents 18:26- 18.13: Benzylic Bromination 21:48- 18.13: Benzylic Bromination- chalk board 25:11- 18.14B: Reduction of Acyl Side Chains 30:40- 18.14B: Reduction of Acyl Side Chains, example 2 33:52- 18.14C: Reduction of NO2 to NH2 39:28- 18.15: Mulit-step Synthesis |