index.html

Chemistry 125
(the Registrar calls it Chem 124)

Freshman Organic Chemistry
Fall 2009

If you are viewing this page on Yale Classes*V2, you should point your browser to
https://webspace.yale.edu/chem125
so you have more space. (We use ClassesV2 mostly for Wiki and Schedule.)

Chem 125 lecture videos, transcripts, and other material from Fall 2008 are available by clicking here (Open Yale Courses)
The videos only are mirrored here (YouTube)

Click to go to Spring Semester

Material for First Quarter of the Fall Semester 2009

Material for Second Quarter of the Fall Semester 2009

Material for Third Quarter of the Fall Semester 2009

Material for Fourth Quarter of the Fall Semester 2008

Syllabus and Course Mechanics

(Discussion Sections) (Exams & Grading)

Material from the first quarter of the Fall Semester 2009

Goals of Chem 125
Do read this

Advice from Alumni
More evaluations are available through http://students.yale.edu/oci/
You may want to check fall term reports for Chem 125 (2006, 2007) as well as the new name Chem 124 (2008)

Lecture 1 (9/2/09) Viewing Instructions
(2009 ppt) (2009 audio file mov) (2008 mov)
(Course Mechanics ; The BIG Question ; The Royal Society ; Pepys as a model Chem 125 student)

Note: the 2009 powerpoint file linked above is a timed file. You can run it without timing, so as to skip around by choosine "Manually" under Slide Show / Set up Show...; or you can run it in synchrony with the audio file by selecting "Browsed by an individual (window)" and "Use timings, if present".

Check the Wiki at ClassesV2 to see if you have been assigned a topic from this lecture.

Samuel Pepys and Isaac Newton - How might they do in Chem 125?

Note the Problems (Due Monday, 9/6/09)

You may work in groups of up to 6 to prepare a group hard copy or e-mail submission (with the names of all participants on it).

Lecture 2 (9/4/09) Viewing Instructions
(2009 ppt) (2009 audio file wma) and/or (2008 mov)

I haven't had time to polish the timed ppt and audio files, which I still hope to do. But in case you'd like to review today's lecture soon, I've posted the ppt, timed as I gave the lecture, and the raw audio in several formats. You can synchronize them yourself, if you wish, by playing them simultaneously and using the right and left arrow keys to make the powerpoint line up with the audio.
Here are some other audio formats, if none of them work for you, please let me know what computer you're using
(mov) (mp3) (wav)

( Force Laws and Springs; Chemical Force Law? ; Lewis's Electron Octet)

note Problems for Friday 9/11/09 on frame 44 (Lewis structure for H/C/N in that order, H/C/H/O in any order)

Newton's Chemistry & the Business of Experimental Philosophy

Two Coulomb Problems (due Wednesday 9/9/09)

Lecture 3 (9/7/09) Viewing Instructions
(2009 ppt folder zipped) (2009 Audio File WMA) and/or (2008 mov)
( Lewis Structures; equilibrium vs. resonance; acetic acid geometry & energy; Lore, O₂/O₃ 4-D plotting; charge distribution; Earnshaw and Faraday's Lines of Force)

What's Wrong with Lewis Structures
What are Force Laws?
Earnshaw via Lines of Force
Shell Structure for Charged Balls in 2D

Dealing with Graphs - Lesson 1

Drill on multidimensional plotting
(you don't need to turn the problems in, but you should know how to do them)
answer key

Problem Set for Friday, 9-11-09(html) or (PDF) or (WORD)
(ignore that these documents are dated for previous years)

Functional Group Table

An organic chemistry course is supposed to have a lot of memorizing. We try to keep this to a minimum, but the minimum isn't nothing. For the first hour exam you will be responsible for memorizing the names of 17 "functional groups" and how to recognize and draw simple "constitutional" structures for them. These functional groups are identified in red in a table that includes 16 additional functional groups that we'll probably encounter this semester. You can access the table in three formats: as a web page ; as a pdf file ; as an downloadable Excel Spreadsheet. I find that sorting a spreadsheet different ways and stepping through it is an effective tool for memorization (that's how I learn your names). Good luck. N.B. the amide functional group is -CONH₂, not -COONH₂, sorry for the typo.

Lecture 4 (9/10/08) Viewing Instructions
(2009 ppt) (2009 audio file wma) and/or (2008 mov)
(Plum Pudding Atoms; Was Coulomb Wrong? Clairvoyant "Science" ; Powers of 10⁵ ; Measuring the very small - Franklin; Feeling atoms SPM, HCNO & Lewis structures)

The first subject of the course is how we know about the existence of atoms, molecules, and bonds. It also teaches about the role of authority in science. To begin we will contrast two erroneous treatments of atomic and molecular structure a century ago. One of them is by two great scientists G. N. Lewis (Lewis dot structures) and J. J. Thomson (discoverer of the electron). The other is by "clairvoyant" frauds.

Seeing Atoms with Clairvoyance (relevant, but not assigned reading)
If you're skeptical that Crookes really believed in psychic pheomena, click here (also not assigned, just for the curious)

SPM web page
Also a humorous question related to the smallness of atoms

It will be VERY helpful to read ahead on the x-ray page

Lecture 5 (9/12/08)
(2009 ppt) (2009 audio file wma) and/or (2008 mov)
(AFM with CO, light and seeing by wave interference, x-ray diffraction, molecular and lattice diffraction )

X-Ray Diffraction

Diffraction examples from laser demonstration

Notice the "What is the line spacing?" question within ppt frame 34. You should work out an answer, so you are confident of understanding.

Lecture 6 (9/14/09)
(2009 ppt) (2009 audio file wma) and/or (2008 mov)
(understanding molecular and lattice diffraction, Franklin's DNA photo; e-density maps, difference maps and bonding)

Leslie Leiserowitz on his Triene (Transcript 16K)
Leiserowitz Quicktime Movie (160 x 120, 5.6 Meg) or (240 x 180, 10.3 Meg)

Jack Dunitz on the C-F Difference Density (Transcript 12K)
Dunitz Quicktime Movie (160 x 120, 6.2 MB) or (240 x 180, 11.2 MB)

(You are not responsible for the page on anomalous dispersion.)

The Second Key Question

It will be VERY helpful to read ahead on the Quantum Mechanics page

Lecture 7 (9/16/09)
(2009 ppt downloads zipped folder containing ppt and Schroedinger sound files) (2009 audio files wma 1 frames 1-18, wma 2 frames 19-30 ) and/or (2008 mov)
(Pathological Bonding; Schroedinger's Invention; Weird Kinetic Energy; The Jeopardy Method, Goldilocks)

Quantum Mechanics (Sections I-V on 1st Exam)

Erwin Meets Goldilocks (problem set due Monday, Sept. 22 - PDF document)

It's a pretty safe bet that you have never worked on this kind of problem before, so you should get started as soon as possible. Although you should learn how to solve all of the problems in this important problem set, it is unrealistic to solve them all by yourself. You should form groups, parcel out the problems, and explain what you learn to one another.

Eugene will demonstrate the use of Erwin Meets Goldilocks at the Thursday discussion section. This program will help you develop a quantum mechanical intuition. You will be doing the relevant problem set in self-selected groups. Be sure that at least one representative from your group (or someone else who is willing to help you) attends the demonstration session. Bring your laptop to the session. It would help if you download the Applet ahead of time.

Java Applet (and download stand-alone at bottom of page)

More Help for getting started with Java program
Erwin Meets Goldilocks ( PDF)

thanks to Yoonjoo Lee

Lecture 8 (9/18/09) Viewing Instructions
(2009 ppt) and/or (2008 mov, see also a transcript) (no 2009 audio file because of operator malfunction - sorry)
(1D Quantum - Erwin meets Goldilocks; Nodes & Quantization; Ψ² & Structure; Vibration, Double Minima)

Lecture 9 (9/21/09) Viewing Instructions
(2009 ppt) ( 2009 audio WMA) or (2008 mov, see also a transcript)
(Double Minima - bonding and tunneling; Chladni - nodes in 2D; H-like atom wave functions; ρ for r, orbital shapes)

Chladni Figure Short Movie (Quicktime - 3MB)

4 Chladni Figures (Quicktime - 9.5 MB)

Quantum Mechanics V: H-like Atoms & problem set

Problems for Wednesday, September 25 :

1) Why are there no Chladni Star Figures with an odd number of branches? (e.g. 3 or 5 radii)
2)Why are the first two cells [(0,0) (1,0)] in Chladni's tables vacant?
3) Compare 1s of H with 2s of C⁺⁵ in Energy
4) Do the six Atomic Orbital problems HERE (also for Atom-in-a-Box Download)
Clicking here links to a Java program that provides some of AiB functionality for a PC.

Lecture 10 (9/23/09) Viewing Instructions
(2009 ppt - downloads zipped folder with ppt file) ( 2009 audio WMA) and/or (2008 mov, also here is a transcript)
(Parts of 2p; Dauger's Atom-in-Box; r² weighting; scaling size and energy; hybridization for orientation and shape; The Problem With Orbitals)

If you are have difficulty with why r² is sometimes used to multiply Ψ² in discussing electron distribution,
you might try these optional problems from a previous year and discuss them with friends or TAs.

Hybridization Animation

Review Session: 8-10 pm Wednesday, Sept. 23, 207 WLH
There are probably be more profitable ways to spend your time (like working with the lectures, or wikis, or quantum readings), but for what they're worth McBride comments at this review session were recorded and are available as a WMA file by clicking here. Some parts may be opaque because they refer to what was written on the blackboard or animated by hand gestures. Bear in mind that you're responsible for understanding only what was said in lecture or appeared in required readings or problems. Supplementary readings are for fun. Wikis are for clarifying what was in lecture (or problem sets).

There will be other Review Sessions on Thursday 7-10, 211 WLH (Eugene and Peer Tutors)

You will have a full hour to write Friday's exam. You may start at 10:30 and end at 11:30 in the normal lecture room (160 SCL)
or if it's important to get somewhere else by 11:30, you may choose the early option: start at 10:15 and end at 11:15.
For the "early option" come to Room 111 SCL (at the other end of the hall from 160).

You may be wondering what kind of questions might appear on exams in this course. (Our first exam will occur on Friday, Sept. 25 The following PDF file contains a number of questions based on topics we have been discussing. Most of these would be fair game, but a few from earlier years refer to material we won't cover until shortly after the first test. It might be useful to look them over as we go along.

2001 First Exam (PDF)	Answer Key for 2001 First Exam (PDF)
First Hour Exam 2002 (PDF)	Answer Key for First Hour Exam 2002 (PDF)
	Answer Key for Exam 1 2003 (PDF)
First Hour Exam 2004 (PDF)	First Hour Exam 2004 Answers (PDF)
First Hour Exam 2005 (PDF)	First Hour Exam 2005 Answers (PDF)
First Hour Exam 2006 (PDF)	First Hour Exam 2006 Answers (PDF)
First Hour Exam 2007	First Hour Exam 2007 Answer Key
First Hour Exam 2008 (pdf)	First Hour Exam 2008 Answer Key(pdf)

Sample questions for first hour exam

Sample Quantum Mechanics Questions (PDF)

Sample questions on Early Topics (PDF)

First Hour Exam 2009 (pdf) First Hour Exam 2009 Answer Key(pdf)

The first exam papers will be returned in class on Monday, 9/28/09 (or the Sunday evening by Peer Tutors). Scores are available via Post'em.

The class average was very good (77) with 1/3 of the scores greater than 79 and 2/3 of the scores greater than 74. Congratulations, you seem to be learning a lot!

You can check your own points, both by question and total, using Post'em on ClassesV2. If you have questions about the grading, consult the answer key (above) first, and then speak to the grader of the relevant question (1-4, Douglass; 5 and 7, Jordan; 6 and 8-9, McBride).

The "letter grades" posted are of course almost insignificant, because they represent such a small, preliminary portion of the grading for the semester. But the course content is cumulative, so it can be helpful to see where you stand thus far, and whether it is important to be sure you're not falling behind.

There is plenty of help available from the teaching staff. 5/6 of the semester scoring is still to come, so it's way too early either to despair or to become self-satisfied. The plot to the right from several years ago shows that the first exam score was not a great predictor of semester total. There is some correlation, but it is easy by working (or not) to move up (or down) by a letter grade.

Material for the second quarter of the Fall Semester 2009

Lecture 11 (9/28/09)
(Lecture 11 ppt) (2009 Audio wma) or (2008 mov)
( 2-electrons, Z_eff, SCF, "Correlation Energy", Energy Magnitudes; Orbital Shapes; "Plum-Pudding" molecular orbitals)

Quantum Mechanics VI-VII
(orbitals for several electrons, hybridization)

Energy Scales and Correlation Energy

Lecture 12 (9/30/09)
(Lecture 12 ppt) (2009 Audio wma) or (2008 mov)

("Plum-Pudding" molecular orbitals; Pairwise LCAO-MO, Bonding in H₂, C-C Overlap)

Quantum Mechanics VIII-IX
(molecular orbitals; HOMOs and LUMOs for functional groups)

H-H Bonding

C-C Overlap and Hybridization

Lecture 13 (10/2/09)
(Lecture 13 ppt) (2009 Audio wma or (2008 mov)
(C-C Overlap & Hybridization, Overlap & Energy, Newton's Grail; Energy-Match, H₂ vs. HF, hybridization & geometry)

Overlap / E-Match / Tunneling

Lecture 14 (10/5/09)
(Lecture 14 ppt) (2009 Audio wma 1st 25 min only, sorry) or (2008 mov)
(XH₃: IR, ESR, CF₃; Goals; Pathological Bonds; BH₃and local bonds)

XH₃ (contact with reality)

BH₃, an Example of an MO Computation & an Apology for Local Bonds
Note: the pictures on this page are fun to look at, but don't worry too much about the verbal content,
unless you can't sleep because we use local bond analysis instead of the MOs that computers find.

Lecture 15 (10/7/09)
(Lecture 15 ppt) (2009 Audio wma) or (2008 mov)
(BH₃ and local bonds; Which mixings are important?; Acid-Base Theory; What makes HOMO high, LUMO low? B₂H₆)

HOMO-LUMO Reactivity:

MO Interactions, which ones count? (HOMO/LUMO)Functional Groups (high HOMO base / low LUMO acid)

Lecture 16 (10/9/09)
(Lecture 16 ppt) (2009 Audio wma) or (2008 mov & mov)
(Notice that we are now nearly a lecture ahead of last year's pace, hence two 2008 mov files)
(HF LUMO; Acid-Base - SN2 - E2 LUMO Analogies; Make & Break; N₂H₄ Synthesis; Four Functional Groups: Carbonyl I)

Orbital Shapes of:	HF an acid (substitution at H)
	CH₃F substitution at C (an acid)
	O=CH₂ the carbonyl group (an acid)

LUMO Analogies (elimination from C₂H₅X)

Where should R₂C=O be attacked? (Buergi-Dunitz Angle)

A special Wiki assignment is due Wednesday evening in which you are to discuss a functional group of your choice in terms of pair-wise and atomic orbitals (and their interactions). You should go to the Home/Functional_Group_Analysis_Problem Wiki page and stake your claim to your favorite group as soon as possible. Two people per functional group - first come, first served.

If you would like optional problems to help firm up your understanding of quantum mechanics before the exam a week from Monday (Oct. 19), you could look at the exams from previous years linked below.

I will be giving a quantum mechanics review session next Wednesday evening. We can discuss the time (7-9 or 8-10).

Lecture 17 (10/12/09)
(Lecture 17 ppt) (2009 Audio wma) or (2008 mov & mov)
(Four Functional Groups: carbonyl-Buergi-Dunitz, amide, carboxylic acid, C-metal bond, How Did They Know?)

Note: the last half-hour of the wma recording (beginning at 57:30) contains the optional after-class demonstration of Spartan in which MOs of an enol were calculated and compared with class-member predictions. After the END frame of the Lecture 17 ppt, there is a supplementary timed ppt showing some screen shots from the demonstration. This is optional, not required reading/listening, but it may help to make the computer's contribution less vague.

Intramolecular HOMO/LUMO mixing and "Resonance"

3-Center "Electron-Deficient" "Y" Bonds
[ B₂H₆ & (CH₃Li)₄•4 OMe₂]

OMO-OMO Mixing Problem
(not to turn in, but you may want to discuss it)

History (how humans actually learned about organic chemistry)

History Index

Why we study chemical history (DO READ THIS & the others)

Optional bargain book (popular account of 19th Cent organic chemistry):
Chasing the Molecule by John Buckingham.
(List Price: $24.95) Daedalus Item Code: 84237 Sale Price: $6.98

Lecture 18 (10/14/09)
(Lecture 18 ppt) (2009 Audio wma) or (2008 mov)
(Precursors of Modern Chemistry- Alchemy, Scheele's Acids; Oxygen; Lavoisier's Revolution: Nomenclature, Traité, Analysis, Elements, Measuring Gases, Radicals & Language, Measuring Heat)

Your Genealogy in Organic Structure Theory

Prerevolutionary contributions - Scheele

Lecture 19 (10/16/09)
(Lecture 19 ppt) (2009 Audio wma) or (2008 mov)
(Lavoisier: Analysis & Bookkeeping; Dalton: Atoms & Proportions; Berzelius: Symbols & Analysis)

NOTE: This lecture will be covered on subsequent exams, not this exam. Concentrate on quantum mechanics (and Lect 18).

Lavoisier & the Chemical Revolution: Analysis

(14 Questions for Wednesday, Oct 21, indicated by * below (you may work in groups)

Portrait (we discuss the problem re. Fig. 10 in class, you need not turn it in)
Combustion of Phosphorus and Carbon *4
Quantitative Chemical "Formulae" *4
1789 Preface
Elements & Oxidation *2
How to determine Gas Density
Calorimeter *4

Review Sessions for Monday's Exam

Prof. McBride will lead a session focused on quantum mechanics - Wednesday, Oct. 14, 8-10 pm in 207 WLH.

Eugene will have his normal session on Thursday evening, and the Peer Tutors will have their regularly scheduled help session on Sunday evening.

Sample Problems for Monday's Exam

2nd Hour Exam 2008 (pdf)	2nd Hour Exam 2008 Answers (pdf)
2nd Hour Exam 2007 (PDF)	2nd Hour Exam 2007 Answers (PDF)
2nd Hour Exam 2006 (PDF)	2nd Hour Exam 2006 Answers (PDF)
2nd Hour Exam 2005 (PDF)	2nd Hour Exam 2005 Answers
2nd Hour Exam 2004 (pdf)	2nd Hour Exam 2004 Answers (pdf)
2nd Hour Exam 2003 (pdf)	2nd Hour Exam 2003 Answer Key (pdf)
2nd Hour Exam 2002 (Word)... (PDF)	2nd Exam 2002 Answers (Word)... (PDF)
2nd Hour Exam 2001 (PDF) ... (Word)
2nd Hour Exam 2000 (Word)	Answers to 2000 2nd Exam
2nd Hour Exam 1999 (web page)	(answers at end)
2nd Hour Exam from 1998 (Word)	Answers to 1998 2nd Exam

The exam will take place at 10:30 AM (normal lecture time) in SCL 160 (normal lecture room). It will be budgeted for 50 minutes, but 60 minutes will be allowed for writing exam papers. To accommodate students who must leave for the following class (or who just wish to get it over with), the exam may be taken early from 10:15-11:15 in SCL 111 (southeast corner of SCL - at other end of the hall from 160).

2nd Hour Exam 2009 (pdf) Answers to 2nd Exam 2009 (pdf)

Material for 3rd Quarter of First Semester 2009

(Note QUESTIONS above, due Oct 21)

Lecture 20 (10/21/09)
(Lecture 20 ppt) (2009 Audio wmv) or (2008 mov)
(Gay-Lussac Volumes; Mitscherlich As/P ratio; Berzelius: Analysis, Electrolysis & Dualism; Woehler & Urea; Isomerism)

Combustion Analysis Lavoisier/Prout/Liebig/Dumas (1788-1841)

Note: problems for Monday, October 26 (on web pages with red years 1828 and 1832 below)

Liebig's Kaliapparat and the etymology of K and Na (1831)
Distillation and the "Liebig" Condenser (1771)

1828-1851 Isomerism
Radical (Dualistic) vs. Type (Unitary, Substitution) Theory

Woehler/Berzelius Letters about Urea (1828)
Woehler's Urea Paper (1828) (analysis and isomerism preview)
Berzelius Coins the Term Isomeric (1830)
Woehler/Berzelius on Liebig, Isomerism, & Organic Chemistry (1830-35)
Woehler/Liebig Discovery of Benzoyl Radical (1832) (by analysis)
Dumas's Panegyric on the Radical Theory (1837)
Berzelius on Dumas Substitution Theory (1838)
Simple Alkane Etymology
Woehler's Spoof of the Type Theory (1840)
Competing Views of Organic Chemistry (~1851)

Lecture 21 (10/23/09)
(Lecture 21 ppt now downloads zipped folder including movie of Liebig's Invention for frame 6) (2009 Audio wmv) or (2008 mov)
(Liebig Analysis; Radical Theory; Addition and Substitution Reaction Mechanisms)

Lecture 22 (10/26/09)
(Lecture 22 ppt) (2009 Audio wmv) or (2008 mov)
(Type Theory; Valence: Couper, Structure; Kekulé, Nomenclature)

1858-1860s Constitution
"Nature and Sequence of Bonds"
Couper On a New Chemical Theory (1858)
Kirkintilloch Movie (11Mb)
Kekulé on the Superiority of his Sausage Formulae (1865)
Other Molecular Diagrams and Models (mid 1860s)
Cannizzaro, the Cautious Revolutionary, on Models (1872)

Lecture 23 (10/28/09)
(Lecture 23 ppt ) (2009 Audio wmv) or (mov)
(Notation, Models, Counting Isomers)

Note Problems for Friday on Frame 21
(The isomer counting problem on frame of Lecture 23 should be done for Friday, but I said Monday in Lecture, so if you want to be late, it's OK.)

1869-1880 Configuration
"Arrangement of Atoms in Space"

Koerner Proves 6-fold Symmetry of Benzene (1869)
Paternó's Tetrahedral Carbons (1869)

Lecture 24 (10/30/09)
(Lecture 24 ppt ) (2009 Audio wmv) or (2008 mov)
( Koerner's Benzene Proof, Paterno's tetrahedral carbon)

Lieben to Paternó on Atoms in Space (1869)

Lecture 25 (11/2/09)
(Lecture 25 ppt ) (2009 Audio wmv - sorry, only first 20 min) or (2008 mov)
(Benzene Structure - van't Hoff vs. Ladenburg; Carvone/Tartaric Acid Isomerism; Pasteur, van't Hoff)

van't Hoff's Tetrahedral Carbon (configuration) (1875)
Kolbe's Criticism of van't Hoff (1877)
Your Teacher, a Later-Day Kolbe?

Lecture 26 (11/4/09)
(Lecture 26 ppt ) (2009 Audio wmv) (2008 mov)
(van't Hoff, Tetrahedral C; Coordinate Transformation; Alkenes & Allenes; Mirrors & Alice; Chirality; Stereochemistry; Notation)

Fischer on Models and the Fischer Projection (1891)

Lecture 27 (11/6/09)
(Lecture 27 ppt) (2009 Audio wmv) (2008 mov)
(Counting Configurational Isomers; Systematic Nomenclature for Constitution; Fischer's Ambiguous DL Nomenclature for Configuration)

Problem for Monday (based on frames 17-18 of Lecture 27)
In 1927 P. A. Levene et al. used reaction with HI to convert butane-1,3-diol into 4-iodobutane-2-ol and thus related their stereochemical configurations. In 1952 young K. B. Wiberg worried that an alternative mechanism for this conversion might invalidate Levene's conclusion. Use HOMO-LUMO analysis for possible reactions to see what worried Wiberg. At each reaction step consider alternative possibilities for reaction. (You may work in groups on this problem.)

Sample Nomenclature Drill (Yale only)

Old Third Exams for Practice :
Note - we are ahead of the pace for several previous years and very slightly ahead of last year,
so different material covered in some of the earlier exams will be relevant this year.

3rd Hour Exam 2003 (pdf) ...3rd Hour Exam 2003 Answer Key (pdf)

3rd Hour Exam 2004 (pdf) 3rd Hour Exam 2004 Answer Key (pdf)

3rd Hour Exam 2005 (pdf) 3rd Hour Exam 2005 Answer Key (pdf)

3rd Hour Exam 2006 (pdf) 3rd Hour Exam 2006 Answer Key (pdf)

3rd Hour Exam 2007 (pdf) Sorry, no answer key
(even earlier exams available in the table below)

2002 questions (pdf)	2002 answers (pdf)
2001 questions (pdf) (Word)	2001 answers (pdf) (Word)
2000 questions (pdf) (Word)	2000 answers (pdf) (Word)
1999 questions (pdf) (Word)	sorry, answer key unavailable
1998 questions (pdf) (Word)	1998 answers (pdf) (Word)

The exam will be offered 10:15-11:15 in 111 SCL and 10:30-11:30 in 160 SCL

3rd Hour Exam 2008 (pdf) 3rd Hour Exam 2008 Answer Key (pdf)

Exam Score Statistics 2009 Mean 1/3 of scores > 2/3 of scores >
3rd Exam 81.2 85 77
Sum of 3 Exams + 15 Wikis 268.8 276 258

3rd Hour Exam 2009 (pdf)
3rd Hour Exam 2009 answer key (pdf)

4th Quarter of Fall Semester 2007

Lecture 28 (11/9/09) Prof. K. B. Wiberg guest lecture
(2009 mov or mp4) (2009 audio wma) (2008 Laurence D. Barron on Optical Rotation mov)
(Wiberg describes some of his contributions to classical configuration correlation and the calculation of optical rotatory strength)

Lecture 29 (11/13/09)
(2009 ppt frame 9 modified ~3 p.m.) (2009 audio wma) (2008 mov and mov)
(Systematic Nomenclature for Absolute Configuration - CIP; Resolution)

Stereochemical Nomenclature: Cahn-Ingold-Prelog
Chirality in the 8^th Century (note Problem for Monday)

Lecture 30 (11/16/09)
(2009 ppt) (2009 audio wma) (2008 mov)
( Resolution; Aldol ReactionWho Cares?; Enantiospecificity; Chiral Drugs; Stereo Viewing; Esomeprazole: name and chirality)

(Stereo Viewing this is optional, ask if you're interested)

Lecture 31 (11/18/09)
(2009 ppt) (2009 audio wma) (2008 mov and mov)
(Esomeprazole: Mode of Action, Chiral Switch, Clinicin Perspective, Litigation, Resolution)

Thalidomide/Ritalin Chiral Switch

Lecture 32 (11/20/09)
(2009 ppt) (2009 audio wma) (2008 mov and mov)
(Resolution & Chiral Synthesis, Sharpless Allylic Oxidation; Omeprazole Mechanism; Conformation & Energy; Newman Projection; Rotational Barrier from Heat Capacity)

Lecture 33 (11/30/09)
(2009 ppt) (2009 audio wma) (2008 mov )
(Source of Barrier; Stereotopicity and Toponomy; Baeyer Strain Theory: Sachse's Rhetoric; Mohr's Drawings)

Topicity: Prochirality and Dehydrogenase

1885- Conformation & "Strain"

Baeyer Proposes Strain Theory (1885)

Sachse Identifies Conformational Isomers; Baeyer objects (1890-93)

Mohr Vindicates Sachse (1918)

Lecture 34 (12/2/09)
(2009 ppt) (2009 audio wma) (2008 mov and end of mov)
(Drawing Cyclohexane; Barton's Conformational Analysis; Ring Flips; Rotational Barriers; Strain Energy and Molecular Mechanics)

Drawing Perspective Views of Cyclohexane

Strain Energy in Butane

Lecture 35 (12/4/09)
(2009 ppt) (2009 audio MP3 N.B. this is an MP3 file because I had difficulty editing the wma. Tell me if you have trouble with it.) (2008 mov )
(Axial vs. Equatorial Energy; Ring Relaxation; MM vs. Quantum; Generic Geometries and CSD; Energy Models)

Non-Spherical Bromine

Lecture 36 (12/7/09)
(2009 ppt) (2009 audio wma) (2008 mov )
(Energy Models; Heat of Formation; Average Bond Energies; deltaH_atomCarbon, "effects" in ketone-enol equilibrium; Statistics and Equilibrium)

Energy
Energies: Choice of Zero and Chupka's Heat of Atomization of Carbon

Lecture 37 (12/9/09)
(2009 ppt) (2009 audio wma) (2008 mov )
(Statistics and Equilibrium; The Chemical Bond; Leiserowitz on Hemozoin Crystals and Malaria)

Relevant websites:
Boltzmann Distribution
Distributions - Maxwell to Bush (powerpoint) (marginal relevance)
Entropy & Disorder Riddle

REMAINING REVIEW SESSIONS:

Wednesday, Dec. 16, 8-10 PM (WLH 208) McBride
This session was recorded. If you wish you can check anything that was said here
(though there may be more effective ways to spend your review time)

Thursday, Dec. 17, 7-9 PM (WLH 211) Eugene and Peter

First Semester Final Exam

9 AM Friday, December 18

SPL 59

The exam will be budgeted for 150 minutes, but you will have 180 minutes to complete it. Roughly half of the questions will be focussed on material since the third hour exam. (If half of the final covers the last quarter of the course, and the final counts for half of the semester points, the last quarter of the course counts for 1/4 of the semester total.)

Previous Fall Final Examinations:

Note: Some previous exams covered a few more topics that we did not cover this year. You are responsible only for what was presented in lecture this year and for assigned reading and problems.

1999 First Semester Final Exam (pdf 128kB) and Answer Key (pdf 68kB)