Organic Chemistry
Chem 51C
Spring 2012

VIDEOS

Video recordings of the class lectures will be available through UCI's OpenCourseWare, YouTube, and UCI's download server roughly one week after each class is given. (The delay in posting the videos represents time needed for editing and processing.) Videos can be viewed online from UCI's OpenCourseWare website in streaming format or via YouTube. Links to individual videos are provided below. Please note that viewing the lectures on video is not a substitute for attending lecture, which is mandatory unless you are ill.

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.

Video's are being produced by UCI's OpenCourseWare initiative http://ocw.uci.edu/Welcome.aspx . For a fun composite of UCI's video efforts, see http://www.youtube.com/watch?v=T2nGYwmh_1s .

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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical%20sciences/chemistry/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/ocw/physical sciences/chemistry/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/ocw/physical sciences/chemistry/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/ocw/physical sciences/chemistry/Chem51C/20120607_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