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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)

CHEM 532 Syllabus

CHEM 532 Course policies

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 1 answer key

Problem Set 2 (due Mon., Oct.. 6, 11 a.m. at start of class)

    Problem Set 2 answer key

Problem Set 3 (due Fri., Oct.. 24, 11 a.m. at start of class)

    Problem Set 3 answer key

Problem Set 4 (due Fri., Nov. 14, 11 a.m. at start of class)

    Problem Set 4 answer key

Problem Set 5 (due Wed., Dec. 10, 11 a.m. at start of class)

 

Practice Midterm Exam 1 (key)

    Practice Midterm Exam 1 (blank)

Midterm Exam 1 (key)

    Midterm Exam 1 (blank): if you want to use this for practice

Practice Midterm Exam 2 (key)

    Practice Midterm Exam 2 (blank)

Midterm Exam 2 (key)

    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)

Alkane melting points

HGS Molecular model sets

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

    Zhou et al. (List) Angew. Chem. 2008 manuscript on organocatalytic aldol reaction (vol. 47, issue 40 cover image)

    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

Griesbeck et al. Angew. Chem. 2007 manuscript on singlet oxygen ene reaction and artemisinin core structure

    Alberti et al. Org. Lett. 2008 manuscript on singlet oxygen ene reaction

Hickenboth et al. Nature 2007 manuscript on electrocyclic ring-opening reactions and mechanical force