Organic
Chemistry
Chem 51C
Lecture Videos, Chem 51C Spring 2012
Video recordingss of the Spring 2012 Organic Chemistry 51C class were were produced by UCI's OpenCourseWare initiative http://ocw.uci.edu . Videos can be viewed online from UCI's OpenCourseWare website in streaming format or via YouTube. Links to individual videos are provided below. A
playlist of the YouTube videos is also available at http://www.youtube.com/playlist?list=PL47B3E3FDB175BB8B&feature=view_all . Videos are also available for in .mp4 file format for download to your computer or mobile device. The files are approximately 2 Gb in size and require a fast internet connection (and
patience) to download. To download videos on a Macintosh, hold the Option key
and click with the mouse. To download on a Windows computer, use the right
mouse button.
Please note that viewing the lectures on video is not a substitute for attending lecture, which is mandatory unless you are ill.
Tuesday, April 3
Lecture 1. Introduction to Chem
51C. Ch. 19. Introduction to Carboxylic Acids.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/Introduction-to-Carboxylic-Acids.aspx
YouTube: http://www.youtube.com/watch?v=hZq7vDvmTZg
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120403_nowick_chem51c.mp4
Lecture-Specific
Tags: nomenclature, physical and spectroscopic properties, acidity, basicity,
pKa, acid-base equilibria
Chapter-Specific Tags: carboxylic acids
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Thursday, April 5
Lecture 2. Ch. 20. Reactivity of
Carbonyl Compounds. Reduction of Aldehydes and Ketones
with Hydride Nucleophiles.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/Chem-51C-Spring-2012-Reactivity-of-Carbonyl-Compounds-Reduction-of-Aldehydes-and-Ketones-with-Hydride-Nucleophiles.aspx
YouTube: http://www.youtube.com/watch?v=w8l3bm3VlgU
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120405_nowick_chem51c.mp4
Lecture-Specific
Tags: reducing agent, lithium aluminum hydride, sodium borohydride, oxidation
state
Chapter-Specific Tags: carbonyl group, aldehyde, ketone, nucleophile,
carboxylic acid, ester
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Tuesday, April 10
Lecture 3. Ch. 20. Reactions of Organometallic Reagents with Carbonyl Compounds.
Reactions of Members of the Carboxylic Acid Family with
Hydride Nucleophiles and Organometallic Reagents.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/Chem-51C-Spring-2012-Reactions-of-Organometallic-Reagents-with-Carbonyl-Compounds-and-Carboxylic-Acid-Derivatives-with-Hydride-and-Organometallic-Reagents.aspx
YouTube: http://www.youtube.com/watch?v=ZLa6AsmXp50
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120410_nowick_chem51c.mp4
Lecture-Specific
Tags: Grignard reagents, organolithium reagent, addition-elimination mechanism,
retrosynthetic analysis
Chapter-Specific Tags: carbonyl group, aldehyde, ketone, nucleophile,
carboxylic acid, ester
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Thursday, April 12
Lecture 4. Ch. 20. Selective Reactions and Protecting
Groups in the Chemistry of Carbonyl Compounds and Organometallic Reagents.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/Chem-51C-Spring-2012-Selective-Reactions-and-Protecting-Groups-in-the-Chemistry-of-Carbonyl-Compounds-and-Organometallic-Reagents.aspx
YouTube: http://www.youtube.com/watch?v=6QVeJWUh0fM
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120412_nowick_chem51c.mp4
Lecture-Specific
Tags: chemoselectivity, regioselectivity, protecting group, retrosynthetic
analysis, protecting group, silyl ether
Chapter-Specific Tags: carbonyl group, aldehyde, ketone, nucleophile,
carboxylic acid, ester
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Tuesday, April 17
Lecture 5. Ch. 21. Aldehydes
and Ketones: Reactions with Basic Nucleophiles and Acid-Catalyzed Reactions
with Weakly Basic Nucleophiles.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/Chem-51C-Spring-2012-Aldehydes-and-Ketones-Reactions-with-Basic-Nucleophiles-and-AcidCatalyzed-Reactions-with-Weakly-Basic-Nucleophiles.aspx
YouTube: http://www.youtube.com/watch?v=8mA9y3l4uK4
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120417_nowick_chem51c.mp4
Lecture-Specific
Tags: nomenclature, physical and spectroscopic properties, cyanohydrin, Wittig
reaction
Chapter-Specific Tags: carbonyl group, aldehyde, ketone, nucleophile, pKa,
acidity, basicity
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Thursday, April 19
Lecture 6. Ch. 21. Formation of Imines and Enamines from Aldehydes and Ketones.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/Chem-51C-Spring-2012-Formation-of-Imines-and-Enamines-from-Aldehydes-and-Ketones.aspx
YouTube: http://www.youtube.com/watch?v=ofXS7MG1bCo
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120419_nowick_chem51c.mp4
Lecture-Specific
Tags: imine, enamine, aldimine, ketimine, hemiaminal, carbinolamine, iminium
ion, reaction mechanism, acid-base catalysis
Chapter-Specific Tags: carbonyl group, aldehyde, ketone, nucleophile, pKa,
acidity, basicity
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Tuesday, April 24
Lecture 7. Ch. 21. Acid-Catalyzed Formation of Hydrates, Hemiacetals, and Acetals from
Aldehydes and Ketones.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/Chem-51C-Spring-2012--AcidCatalyzed-Formation-of-Hydrates-Hemiacetals-and-Acetals-from-Aldehydes-and-Ketones.aspx
YouTube: http://www.youtube.com/watch?v=cY5NY5npaXE
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120424_nowick_chem51c.mp4
Lecture-Specific
Tags: hydrate, geminal diol, hemiacetal, acetal, acid-catalyzed, reaction
mechanism, protecting group
Chapter-Specific Tags: carbonyl group, aldehyde, ketone, nucleophile, pKa,
acidity, basicity
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Thursday, April 26
Lecture 8. Ch. 22. The Chemistry of the Carboxylic Acid Family. Reactions of Acid Chlorides and Anhydrides.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/Chem-51C-Spring-2012-Chemistry-of-the-Carboxylic-Acid-Family-Reactions-of-Acid-Chlorides-and-Anhydrides.aspx
YouTube: http://www.youtube.com/watch?v=-VAmek4cAqs#!
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120426_nowick_chem51c.mp4
Lecture-Specific
Tags: nomenclature, physical and spectroscopic properties, reaction mechanism,
pKa, amine, alcohol, nucleophile
Chapter-Specific Tags: carboxylic acid, ester, amide, acid chloride, anhydride,
nitrile
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Tuesday, May 1
Lecture 9. Ch. 22. Reactions of Carboxylic Acids, Esters,
Amides, and Nitriles.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/chem-51c-spring-2012-reaction-of-carboxylic-acids-esters-amides-and-nitriles.aspx
YouTube: http://www.youtube.com/watch?v=T7qI2hBmRTE
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120501_nowick_chem51c.mp4
Lecture-Specific
Tags: Fisher esterification, reaction mechanism, acid-catalyzed, hydrolysis,
nucleophile, alcohol, water, amine
Chapter-Specific Tags: carboxylic acid, ester, amide, acid chloride, anhydride,
nitrile
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Thursday, May 3
Lecture 10. Ch. 23. Enols and
Enolates.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/chem-51c-spring-2012-enols-and-enolates.aspx
YouTube: http://www.youtube.com/watch?v=MjWV_oLsDns
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120503_nowick_chem51c.mp4
Lecture-Specific
Tags: tautomer, acid-catalyzed, reaction mechanism, pKa, alkylation
Chapter-Specific Tags: enol, enolate, ketone, aldehyde
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Thursday, May 10
Lecture 11. Ch. 23. More Reactions
of Enols and Enolates.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/chem-51c-spring-2012-more-reactions-of-enols-and-enolates.aspx
YouTube: http://www.youtube.com/watch?v=ea1iYgxVCn0
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120510_nowick_chem51c.mp4
Lecture-Specific
Tags: electrophile, alpha-halogenation, haloform reaction, pKa, alkylation,
acetoacetic ester synthesis, malonic ester synthesis, methyl ketone, carboxylic
acid
Chapter-Specific Tags: enol, enolate, ketone, aldehyde
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Tuesday, May 15
Lecture 12. Ch. 24. The Aldol Reaction and the Michael
Reaction.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/Chem-51C-Spring-2012-The-Aldol-Reaction-and-the-Michael-Reaction.aspx
YouTube: http://www.youtube.com/watch?v=iP7GORVCA9M
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120515_nowick_chem51c.mp4
Lecture-Specific
Tags: LDA, aldol reaction, elimination, E1cB, dehydration, crossed aldol
reaction, intramolecular aldol reaction, Michael addition, Michael reaction
Chapter-Specific Tags: aldehyde, ketone, ester, enolate, retrosynthetic
analysis
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Thursday, May 17
Lecture 13. Ch. 24. The Robinson Annulation and the
Claisen Reaction.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/chem-51c-spring-2012-the-robinson-annulation-and-the-claisen-reaction.aspx
YouTube: http://www.youtube.com/watch?v=R3i2E77sfIo
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120517_nowick_chem51c.mp4
Lecture-Specific
Tags: Robinson annulation, Claisen reaction, condensation, Michael reaction,
aldol reaction, elimination, E1cB, dehydration, crossed Claisen reaction,
Dieckmann reaction, intramolecular
Chapter-Specific Tags: aldehyde, ketone, ester, enolate, retrosynthetic
analysis
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Tuesday, May 22
Lecture 14. Ch. 25. Introduction to Amines: Properties
and Synthesis.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/chem-51c-spring-2012-introduction-to-amines-properties-and-synthesis.aspx
YouTube: http://www.youtube.com/watch?v=NR_jnYvZC_0
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120522_nowick_chem51c.mp4
Lecture-Specific
Tags: nomenclature, physical and spectroscopic properties, basicity, pKa,
reductive amination, Gabriel synthesis
Chapter-Specific Tags: amine
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Thursday, May 24
Lecture 15. Ch. 25. Reactions of Amines: Hofmann
Degradation, Diazotization, and Reactions of Aryl Diazonium Salts.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/chem-51c-spring-2012-reactions-of-amines-hofmann-degradation-diazotization-and-reactions-of-aryl-diazonium-salts.aspx
YouTube: http://www.youtube.com/watch?v=EoXUQ5eNol8
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120524_nowick_chem51c.mp4
Lecture-Specific
Tags: Hofmann degradation, Hofmann exhaustive methylation, Hofmann elimination,
E2, diazotization, diazonium salt, SN1, Sandmeyer reaction, electrophilic
aromatic substitution, azo compound, dye
Chapter-Specific Tags: amine
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Tuesday, May 29
Lecture 16. Ch. 27. Introduction to Carbohydrates:
Structure and Stereochemistry.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/chem-51c-spring-2012-introduction-to-carbohydrates-structure-and-stereochemistry.aspx
YouTube: http://www.youtube.com/watch?v=X-Td7XgrVGg
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120529_nowick_chem51c.mp4
Lecture-Specific
Tags: Haworth projection, Fischer projection
Chapter-Specific Tags: carbohydrate, sugar, monosaccharide, aldose, ketose,
pyranose, furanose, glucose, diastereomer, anomer, epimer, hemiacetal, acetal,
glycosidic linkage
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Thursday, May 31
Lecture 17. Ch. 27. Structure and
Stereochemistry of Carbohydrates (continued). Reactions
of Carbohydrates.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/chem-51c-spring-2012-structure-and-stereochemistry-of-carbohydrates-continued-and-reactions-of-carbohydrates.aspx
YouTube: http://www.youtube.com/watch?v=of1SSbS2Qdk
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120531_nowick_chem51c.mp4
Lecture-Specific
Tags: enantiomer, hydrolysis, reduction, oxidation, Kiliani-Fischer synthesis
Chapter-Specific Tags: carbohydrate, sugar, monosaccharide, aldose, ketose,
pyranose, furanose, glucose, diastereomer, anomer, epimer hemiacetal, acetal,
glycosidic linkage
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Tuesday, June 5
Lecture 18. Ch. 28. (Sections
28.1, 28.5, 28.7 & 28.8) Amino Acids, Peptides, and Proteins.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/chem-51c-spring-2012-amino-acids-peptides-and-proteins.aspx
YouTube: http://www.youtube.com/watch?v=5o0VVMklQ3g
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120605_nowick_chem51c.mp4
Lecture-Specific
Tags: protecting group, Boc, Fmoc, DCC, TFA
Chapter-Specific Tags: amino acid, peptide
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick
Thursday, June 7
Lecture 19. Ch. 26. (Sections
26.1, 26.2 & 26.6) Organometallic Reactions in Organic
Synthesis.
Streaming format from UCI's OpenCourseWare website: http://ocw.uci.edu/lectures/chem-51c-spring-2012-organometallic-reactions-in-organic-synthesis.aspx
YouTube: http://www.youtube.com/watch?v=X033TBYwo2U
Download (mp4 file): http://cast.oit.uci.edu/jsnowick/Chem51C/20120605_nowick_chem51c.mp4
Lecture-Specific
Tags: organotransition metal complex, cuprate, Suzuki reaction, oxidative
addition, transmetallation, reductive elimination, boronic acid, boronic ester,
olefin metathesis, Grubbs catalyst
Chapter-Specific Tags: organometallic reaction, organic synthesis
Course-Specific Tags: organic chemistry, UCI, Chem 51C, Nowick