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Welcome to the website for CHEM 532, Fall 2008
Advanced Physical Organic Chemistry
Welcome back for the
last two weeks of class!
The Final Exam is on Thursday, December 18 at 8:30am-11:00am in
223 Gregory Hall.
Please make
a note of the room location.
(There will be no "practice final exam".)
Problem Set 5 is due
on Wednesday, December 10 (the final lecture)
at the start of class.
The problem set is posted below.
The key will be posted on December 10 after class.
Midterm Exam 2
has been graded; the key is posted below.
Exams scores (average ± standard deviation): 81 ± 10 (n = 28).
Midterm Exam 1 has
been graded; the key is posted below.
Exam scores (average ± standard deviation): 79 ± 10 (n = 28)
Previous undergraduate organic chemistry material (40 pages)
Problem Set 1 (due Fri., Sept. 19, 11 a.m. at start of class)
Eliel pp. 780-781 (relevant for PS1 #3)
Problem Set 2 (due Mon., Oct.. 6, 11 a.m. at start of class)
Problem Set 3 (due Fri., Oct.. 24, 11 a.m. at start of class)
Problem Set 4 (due Fri., Nov. 14, 11 a.m. at start of class)
Problem Set 5 (due Wed., Dec. 10, 11 a.m. at start of class)
Practice Midterm Exam 1 (blank)
Midterm Exam 1 (blank): if you want to use this for practice
Practice Midterm Exam 2 (blank)
Midterm Exam 2 (blank): if you want to use this for practice
IUPAC Compendium of Chemical Terminology (Gold Book)
Nature 2006 article on important chemistry problems
Website on Named Things in Chemistry & Physics
Sarma J. Chem. Educ. 2004 manuscript on chemical etymology
Bradley et al. J. Chem. Educ. 2002 manuscript on sophomore organic chemistry lectures
Larrick & Soll Science 2008 commentary on fuel efficiency measures (MPG)
Whangbo et al. Can J. Chem. 1975 manuscript including bond length of protonated formaldehyde
Energy & equilibrium (also energy & kinetics)
cis-Decalin conformational considerations
Mascal et al. J. Am. Chem. Soc. 2008 ASAP manuscript on interesting oxonium ions
Braniac video demonstration – alkali metal ions in water
Braniac video demonstration – thermite reaction
Schwesinger bases (polyphosphazenes)
Page 465 from L&R: 2-norbornyl carbocation, from exo versus endo
Wiberg Acc. Chem. Res. 1999 manuscript on C=O groups and resonance
Wiberg J. Chem. Educ. 1996 manuscript on C=O groups and electrostatic effects
Balaban et al. Chem. Rev. 2005 manuscript on history of aromaticity
Siegel Angew. Chem. Int. Ed. Engl. 1994 manuscript on Mills-Nixon effect
Mohler et al. Angew. Chem. Int. Ed. Engl. 1990 manuscript on hydrogenation of central benzene ring
Starphenylene hydrogenation structures
Jux Angew. Chem. Int. Ed. 2008 manuscript on Hückel/Möbius aromaticity and porphyrins
Mo & Gao Acc. Chem. Res. 2007 manuscript on steric hindrance vs. hyperconjugation in ethane
Boltzmann gravestone (JPG file)
Alabugin et al. J. Am. Chem. Soc. 2008 manuscript on 5-endo-dig radical cyclization
Claborn et al. Angew. Chem. 2008 manuscript on optical rotation of achiral compounds
Schwan J. Chem. Educ. 1993 manuscript on Hammett analysis
Murdoch J. Chem. Educ. 1981 manuscript on rate-limiting step
Kost & Pross Educ. in Chem. 1977 manuscript on misuse of energy profiles
More O'Ferrall J. Chem. Soc. B 1970 manuscript on energy diagrams
Inoue & Bruice J. Org. Chem. 1986 manuscript on E1cbi mechanism
Loftfield JACS 1951 manuscript on the Favorskii rearrangement
Vougioukalakis et al. Chem. Eur. J. 2008 manuscript - includes b-secondary KIE examples on page 3
List & Yang Science 2006 review on organocatalysis
MacMillan Nature 2008 review on organocatalysis
Nicewicz & MacMillan Science 2008 manuscript on SOMO organocatalysis
Kim et al. Angew. Chem. 2008 manuscript on steric strain and diaza-Cope rearrangement
Rossi & Palacios Tetrahedron 1993 review on SRN1/SRN2 reactions
Bowman & Symons J. Chem. Soc. Perkin Trans. 2 1986 manuscript on SRN1 reaction
Bartlett & Tidwell JACS 1968 manuscript on SN1 solvolysis rates
Diez-Gonzalez & Nolan Angew. Chem. 2008 manuscript on azide-alkyne reaction catalysts
Singleton & Thomas J. Am. Chem. Soc. 1995 manuscript on measuring small KIE
Steigerwald et al. JACS 1979 manuscript on anionic oxy-Cope rearrangement
Carruthers and Coleman, page 241
Ishikawa et al. JACS 2001 manuscript on a [2+3] sigmatropic rearrangement
Ishikawa et al. JACS 2001 retraction of above manuscript due to prior paper by another lab
Craig & Slavov Chem. Commun. 2008 manuscript on LFER for Claisen rearrangement
Alberti et al. Org. Lett. 2008 manuscript on singlet oxygen ene reaction
