Chem 51B: Organic Chemistry II

Video Lectures

Displaying all 26 video lectures.
Lecture 1
Review of Chem 51A
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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
Alcohols, Ethers, and Epoxides - Part 1
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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
Alcohols, Ethers, and Epoxides - Part 2
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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
Alcohols, Ethers, and Epoxides - Part 3
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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
Alcohols, Ethers, and Epoxides Part 4.
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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
Alkenes, Part 1.
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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
Alkenes, Part 2.
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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
Alkenes, Part 3.
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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
Alkynes, Part 1.
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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
Alkynes, Part 2.
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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
Alkynes, Part 3.
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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
Alkynes, Part 4.
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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
Reduction and Oxidation, Part 1.
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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
Reduction and Oxidation, Part 2.
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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
Reduction and Oxidation, Part 3.
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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
Infrared Spectroscopy + Ch. 14.
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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
NMR Spectroscopy.
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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
NMR Spectroscopy, Part 2.
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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
NMR Spectroscopy, Part 3.
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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
Radicals.
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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
Conjugation, Resonance, Diels-Alder Reactions, Part 1.
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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
Conjugation, Resonance, Diels-Alder Reactions, Part 2.
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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
Aromaticity.
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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
Electrophilic Aromatic Substitution.
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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
Electrophilic Aromatic Substitution Part 2.
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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
Electrophilic Aromatic Substitution, Part 3.
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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