Freshman
Organic Chemistry
Spring 2010
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Click Here for First Term Website - Fall 2009
Material for First Quarter of the Spring Semester 2010
Material for Second Quarter of the Spring Semester 2010
Material for Third Quarter of the Spring Semester 2010
Material for Fourth Quarter of the Spring Semester 2010
(Discussion Sections) (Exams & Grading)
Do read this
Lecture 38 (1/11/10)
Reaction Rates: Trajectories, Transition State Theory, and Bond Dissociation Energies
(Lecture 38 ppt) (Lecture 38 ppt zipped with SEM movie and Audio - 38MB) (2010 Audio wma)
Lecture 39 (1/13/10)
Reaction Order Information, Understanding Changes in Bond Dissociation Energies, and Predicting Rate Constants
(Lecture 39 ppt) (2010 Audio wma)
optional rate-limiting-step practice
Lecture 40 (1/15/10)
Predicting Rate Constants and the Reactivity-Selectivity Relation. Rates of Chain Reactions.
(Lecture 40 ppt) (2010 Audio wma part 1 ; wma part 2 sorry for interruption)
Lecture 41 (1/20/10)
Rates of Chain Reactions (ionic effects) and Electronegativity
(Lecture 41 ppt) (2010 Audio wma)
Lecture 42 (1/22/10)
Solvation and Ionophores
(Lecture 42 ppt) (2010 Audio wma)
Lecture 43 (1/25/10)
Solvation, Ionophores, (cont) and Brønsted Acidity
(Lecture 43 ppt) (Lecture 43 ppt zipped with 18-c-6 movie and Audio - 14MB) (2010 Audio wma)
Your answer to the pKa problem in Frame 18 need not be turned in, but it may be relevant later
Here is the link to the pKa Table of Ripkin and Evans
Lecture 44 (1/27/10)
Nucleophilic Substitution Tools - Stereochemistry, Rate Law, Substrate
(Lecture 44 ppt) (2010 Audio wma)
Lecture 45 (1/29/10)
Nucleophile, Leaving Group, Pentavalent Carbon
(Lecture 45 ppt) (2010 Audio wma)
Supplementary Reading:
Pentavalent Carbon and "Proving" the SN2 Mechanism
optional - Nucleophilicity, Basicity, and Linear Free Energy Correlations
Lecture 46 (1/29/10)
E2, SN1, E1
(Lecture 46 ppt) (2010 Audio wma)
There will be a review session Monday evening 8-10 PM in WLH 116 for Wednesday's Exam.
The official room for the Peer Tutor Sunday evening help sessions in Bass L70.
Exam 5 2/9/07 (pdf) Exam 5 Answers (pdf)
Mostly relevant practice questions from two previous 5th exams:
2004 questions 2004 answers
2006 questions 2006 answers
More 2004-06 Questions More 2004-06 Answers
Exam 5 2010 (pdf) Exam 5 2010 Answers (pdf)
Material from the second quarter of the Spring Semester 2009
Lecture 47 (2/5/10)
Addition to Alkenes - A Synthetic Chemist's Perspective
(Lecture 47 ppt) (2010 Audio wma)
Lecture 48 (2/8/10)
Addition to Alkenes - A Physical-Organic Perspective
Alkene Stability, Mechanisms, HX addition, Bridging vs. Rearrangement
(Lecture 48 ppt) (2010 Audio wma)
Lecture 49 (2/10/10)
Electrophilic Addition to Alkenes with Nucleophilic Participation
Halonium, Carbenes, Hydroboration/Oxidation, Carbenoid
(Lecture 49 ppt) (2010 Audio wma)
Lecture 50 (2/12/10)
More Electrophilic/Nucleophilic Addition
Epoxidation/Epoxides, Ozonolysis, Dipolar Cycloaddition
(Lecture 50 ppt ) (2010 Audio wma)
Lecture 51 (2/15/10)
More Addition to Alkenes: Organometallic Reagents and Catalysts
( Lecture 51 ppt) (2010 Audio wma)
Lecture 52 (2/17/10)
Addition by Radicals & Electrophilic Carbon; Isoprenoids; and Polymer Properties
( Lecture 52 ppt) (2010 Audio mov) (2010 Audio mp3)
N.B. .mov and .mp3 formats. Note the audience comment following 42:00.
Lecture 53 (2/19/10)
Tuning Polymer Properties. Alkynes, Dienes, and Conjugation
( Lecture 53 ppt) (2010 Audio wma)
Lecture 54 (2/22/10)
Linear and Cyclic Conjugation: Allylic Intermediates, 4n+2 Aromaticity, Cycloaddition
( Lecture 54 ppt) (2010 Audio wma)
See replacement for frame 5 here: NBS allylic bromination
Lecture 55 (2/24/10)
4n+2 Aromaticity, Cycloaddition, Electrocyclic Reactions
( Lecture 55 ppt) (2010 Audio wma)
McBride Review Session for Friday Exam
8-10 PM, Wednesday Room 207 WLH
(I'll record what I say for those who must miss the session, but it is probably more efficient
to talk with a friend who attended, since you won't have what is drawn on the board.)
Here is the review session recording as an MP3 file (129 Mb)
and here as a QuickTime .mov file (33 Mb)
Exam Friday, February 26
Room 160 10:30-11:30
or Room 111 SCL 10:15-11:15
Practice for Friday's Exam:
Exam 6 2003 (pdf) Answers (pdf)
Exam 6 2004 - Answers only (pdf)
Exam 5 2006 (pdf) Answers (pdf) (Questions 5, 7, 10 relevant for 2010)
Exam 6 2006 (pdf) (sorry no answer key)
Exam 5 2009 (pdf) Answers(pdf) (Questions 1,2,4 relevant for 2010)
Exam 6 2010 (pdf) Answers (pdf)
Material from the third quarter of the Spring Semester 2010
Lecture 56 (3/1/10)
Dewar Benzene, Spectroscopy: Atoms (allowed/forbidden), n-pi*, Lindlar, Axes, IR Frequencies
(Lecture 56 ppt) (2010 Audio wma)
Lecture 57 (3/3/10)
Normal Modes: mixing and independence of local modes in IR spectroscopy, Hydrocarbon chains, Carbonyls
(Lecture 57 ppt) (2010 Audio wma)
Lecture 58 (3/5/10)
"Practical" IR spectroscopy. NMR introduction: Precession and Imaging
(Lecture 58 ppt folder.zip) (2010 Audio wma)
Precession Page Problems
Lecture 59 (3/22/10)
NMR: Peak Integration, Chemical Shift and Diamagnetic Anisotropy, Spin-Spin Splitting
(Lecture 59 ppt) (2010 Audio wma)
Lecture 60 (3/24/10)
NMR: Isotropic J, Dynamics, Predicting Spectra
(Lecture 60 ppt) (2010 Audio wma)
Lecture 61 (3/26/10)
NMR: Decoupling, C-13, Correlation
(Lecture 61 ppt) (2010 Audio wma)
Lecture 62 (3/29/10)
Electrophilic Aromatic Substitution
(Lecture 62 ppt) (2010 Audio wma)
Lecture 63 (3/31/10)
Diazonium Utility, Nucleophilic Aromatic Substitution
(Lecture 63 ppt) (2010 Audio wma)
Sample questions for next Monday's 7th Exam:
Exam 7 2004 (pdf) (questions 5,6,7 would be less relevant this year) Answers (pdf)
Exam 7 2006 (pdf) (questions 5,8 would be less relevant this year) Answers(pdf)
Exam 7 2007 (pdf) (questions 3,6,7 would be less relevant this year) Answers(pdf)
Exam 7 2009 (pdf) (question 7b would be irrelevant this year) Answers(pdf)
Exam Review:
Prof. McBride will be a review session on Thursday evening (8-10 PM, room 116 WLH)
Here is a wma audio recording of the two-hour Thursday review session. It would become much most useful if someone set up a wiki where people could list various topics and the position on the recording where they are discussed.
Eugene will host a session Friday afternoon (2-4 PM, room 18 SCL)
Andrew and Connie will hold the normally scheduled session on Sunday evening.
Hayley will hold a session on Monday evening (time TBA, probably in the Bass cafe) for students who are taking the exam Wednesday morning and unable to attend on Sunday evening. NOTE: to be fair, students may not attend both the Sunday evening and Monday evening sessions, they must choose one.
Those who have been approved for postponing the recent hour exam
may take it Wednesday, April 7, at 9:15 (SCL 111)
Exam 7 2010 (pdf) Answers (pdf)
Material from the fourth quarter of the Spring Semester 2010
Lecture 64 (4/2/10)
C=O Groups - Overview
(Lecture 64 ppt) (2010 Audio wma)
Lecture 65 (4/7/10)
C=O Groups - Oxidation/Reduction
(Lecture 65 ppt) (2010 Audio wma)
Latimer on Atomic Oxidation States
Lecture 66 (4/9/10)
Oxidizing/Reducing Reagents, Bookkeeping & Mechanism
(Lecture 66 ppt) (2010 Audio wma)
Lecture 67 (4/12/10)
Oxidizing/Reducing Reagents, Green Chemistry
(Lecture 67 ppt) (2010 Audio wma)
Lecture 68 (4/14/10)
Mitsunobu Reaction, Acids and Acid Derivatives
(Lecture 68 ppt) (2010 Audio wma)
Lecture 69 (4/16/10)
Acid Derivatives
(Lecture 69 ppt) (2010 Audio wma)
Lecture 70 (4/19/10)
Alpha Reactivity
(Lecture 70 ppt) (2010 Audio wma)
Lecture 71 (4/21/10)
Topics from Ch. 22 - Carbohydrates
(Lecture 71 ppt) (2010 Audio wma)
Lecture 72 (4/23/10)
guest lecture(s) by Prof. Ziegler
Carbohydrates - Fischer's Proof of the Configuration of Glucose
(Lect 72 ppt) copied from Prof. Ziegler on Carbohydrates ppt (2010 Audio wma)
What Fischer actually said: Translation of Fischer Proof pdf
NOTE: Although the Ziegler timed ppts linked above and below are more or less correct, he tells me that
the files were slightly updated and are available (untimed) at this location on his Chem 220 site.
Lecture 72b (4/26/10)
follow-up guest lecture(s) by Prof. Ziegler
(Lect 72b ppt) (2010 Audio wma)
This second lecture in which Prof. Ziegler discusses ring isomers (pyranose, furanose) and dimers (disaccharides) of sugars and how their structures were proven is optional. Wikis were not assigned, and you will not be held directly responsible for its material (other than things you should have been able to figure out whether or not you attended the lecture or looked at related material in the text).
Lecture 73 (4/28/10)
(Lecture 73 ppt) frames 5 and 8 corrected (2010 Audio wma)
Three Condensations & Review: Synthesis of an Unnatural Product (Anti-Aromatic Cyclobutadiene in a Clamshell)
Lecture 74 (4/30/10)
(Lecture 74 ppt) (2010 Audio wma)
Review: Synthesis of a Natural Product (Woodward's Synthesis of Cortisone)
Review Session (5/3/10)
for those who could not attend, here is a recording of the review session and some of the graphics
(2010 Audio wma) (ppt)
(At 1:21:50 in the audio file there is a final question about the geometry of malonic acid decarboxylation. It was difficult to draw this properly on the board, and it looks like a mess in the ppt above. Here is a movie showing the molecule bouncing back and forth across the transition state for transferring a proton from top to bottom to form an endiol at the bottom and lose CO2 from the top. This was the result of a simple SCF MO calculation. Note how the geometry is consistent with overlap to form the new pi bonds. Quicktime.mov)
Remaining Help Sessions:
(as announced to you by e-mails from Eugene and Jon)
Tuesday (May 4) WLH 114 7-9pm
Wednesday (May 5) WLH 113, 7-9
Thursday (May 6) LC 10530 7-9pm
FINAL EXAM:
Friday (May 7) 9am-12noon Room 160 SCL (normal lecture room)
Recent Spring Finals
(Sorry, no answer keys, but most, if not quite all, questions would be fair this year)
Spring Final 2003.pdf
Spring Final 2004.pdf
Spring Final 2006.pdf
Spring Final 2007.pdf
Spring Final 2009.pdf
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