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The following
Computational Chemistry Projects are designed to be used in
conjunction with Organic Chemistry lecture courses as currently
taught at the University of Pittsburgh. These projects utilize
the CAChe software package, reinforce or extend lecture topics, and
require roughly 2 hrs each for a student to thoroughly do and
benefit from the exercises. They were created by graduate
students enrolled in a 1-credit minicourse (Advanced Topics
Organic Chem 1, Summer 2006) that required participation in a
3-day workshop (Computational Chemistry for Chemical Educators).
All rights are retained by the original authors.
| Pitt Courses | Project |
Book & Chapter |
| 0310 / 0730 |
Electrophilic Addition to Alkenes and Alkynes, by
Grzegorz
Filipczyk, June 2006.
(In this exercise the CAChe program is used to model key
structures of the intermediate carbocations in electrophilic
addition to alkenes and alkynes. The minimum energy of each of
the possible intermediate carbocations is used to predict
the products.)
Download
pdf or
doc file. |
Vollhardt & Schore, 5th Ed., Chapters-Section
12-3 & 13-7. |
| 0310 / 0730 |
The Diels-Alder Cycloaddition Reaction, by Matthew M. Davis,
June 2006. (The CAChe software package is used to
calculate the energy of the HOMO and LUMO of various dienes and
dienophiles. From this information the trends in the relative
energy of HOMO’s and LUMO’s are examined in terms of the
substitution of the dienes and dienophiles and using this
information the relative reactivity of several pairs of
Diels-Alder partners is addressed.)
Download
pdf or
doc file. |
Vollhardt & Schore,
4th Ed., Chapter 11 |
| 0320 / 0730 |
Carbonyl Derivatives and IR Spectroscopy, by Jolie DeForrest,
June 2006. (The goal of this computational project is to
allow students to use modeling software to calculate the
geometries of simple carbonyl compounds. The students will then
extract geometric information from these calculations (i.e.,
bond lengths and angles). Finally, the students will calculate
and interpret an IR spectrum of an aldehyde, ketone, ester,
acid, and amide.)
Download
pdf or
doc file. |
Vollhardt & Schore,
4th Ed., Chapter 17 |
| 0320 / 0730 |
Using Molecular Modeling to Analyze Elimination Pathways in
Natural Product Synthesis, by Jennifer Loyer-Drew,
June 2006. (Students will use CAChe to perform qualitative
conformational analysis of an intermediate in the synthesis of a
natural product. Based upon these observations and calculation
of the relative energies of the resulting elimination products,
students will be asked to suggest general elimination conditions
(e.g. bulky/non-bulky base, strong/weak base) that are likely to
lead to the desired elimination product.)
Downloads not yet available. |
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| 0320 / 0730 |
Predicting the Reactivity of a Complex Molecule Using the Heat of
Formation and Electrontatic Potential Calculations Generated
by CAChe, by Jamie McCabe,
June 2006. (The overall objective of this computational exercise is to introduce
the student to ways to use molecular modeling to solve
'real-life' problems in organic synthesis. They will see how
they can use computational analysis to lead the direction of the
reaction sequence instead of trying a reaction in the laboratory
and obtaining an undesired product.)
Download
pdf or
doc file. |
Vollhardt & Schore,
4th Ed., Chapter 18 |
| 0320 / 0740 |
The Haloform Reaction: An Exercise in Computational
Chemistry, by
Ben Norris, June 2006. (The CAChe
program is used to calculate appropriate heats of formation to
help understand why the base-mediated alpha-halogenation
reaction is exhaustive. Additional calculations are used to
examine why the haloform reaction only works with methyl ketones.)
Download
pdf or
doc file. |
Vollhardt & Schore, 5th Ed., Chapter-Section
18-3 . |
| 0320 / 0740 | Properties and
Stability of Carboxylic Acid Derivatives, by
Thomas Painter,
June 2006. (The goal of this assignment is to explore the
electronic and thermodynamic properties of acid derivatives. The
student will observe trends and should be able to draw
conclusions on general stabilities of these compounds. This
exercise should reinforce concepts learned in class.)
Download
pdf or
doc file. |
Vollhardt & Schore, 5th Ed.,
Chapters 19 & 20. |
| 0320 / 0740 |
Glucose: Molecular Modeling with CAChe, by
Mark R. Ams, June 2006.
(This assignment uses CAChe as a tool to verify the chemical
phenomena observed by glucose in real life. CAChe is used to
distinguish between the preferred conformers of glucose in
various solvents, demonstrate the anomeric effect, and create a
potential energy map for the rotational changes of a linked
glucose disaccharide.)
Download
pdf or
doc file. |
Vollhardt & Schore, 5th Ed., Chapter 24 |
| 0320 / 0740 |
Fructose: Molecular Modeling with CAChe, by
Binita Chandra, June 2006. (CAChe is used in this project to examine the relative energies of the
various conformational forms of fructose and understand how the
sterics and the anomeric effect play equally important roles in
determining which conformers are preferred.)
Download
pdf or
doc file. |
Vollhardt & Schore, 5th Ed., Chapter 24 |
| 0320 / 0740 |
Nucleic Acids and Base Pairin, by Erikah
Englund, June 2006. (The students are asked to
model the nucleic acids and run 2 experiments to measure the
electronic isopotential and electronic potential on electron
density. Using information provided concerning the known sites
of hydrogen bonding, the student is then asked to draw
conclusions concerning the electron density at the sites of
hydrogen bond donating and accepting.)
Download
pdf or
doc file. |
Vollhardt & Schore,
5th Ed., Chapter 26, Section 9. |
| 0320 / 0740 |
Conformational Studies on 8-Oxoguanine Residue in DNA-Strands, by
Nihar Sarkar, June 2006. (The modeling experiments in
this project are designed to examine the conformational forms of oxoG (8-oxo-guanine in DNA) and to calculate dihedral angles,
map surface electron densities, draw potential energy curves,
and optimize geometries through the CAChe software package.)
Download
pdf or
doc file. |
Vollhardt & Schore, 5th Ed.,
Chapter 26, Section 9. |
Authorized course instructors
are welcome to email Prof. Grabowski (joeg@pitt.edu)
to request a MS-Word (doc) file complete with suggested answers of any of the
above project files. |
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