Chemistry 125  

Freshman Organic Chemistry

Spring 2011

This website provides materials to support the second term of the two semester sequence Chem 124a-Chem 125b as taught at Yale University Fall 2010-Spring 2011.

It includes such materials as original powerpoint files (timed to synchronize with audio files), movie files with powerpoint and audio together, exams, answer keys, and some problems and supplemental readings.

With support from the William and Flora Hewlett Foundation, Open Yale Courses has made the Chem 125 lectures available in several formats (including live video) for the Fall Term of 2008 and the Spring Term of 2011.

Click Here for First Term Website - Fall 2010

Material for First Quarter of the Spring Semester 2011: Lectures 38-47 (1-10 of OYC)

Material for Second Quarter of the Spring Semester 2011: Lectures 47-55 (10-18 of OYC)

Material for Third Quarter of the Spring Semester 2011: Lectures 56-65 (19-28 of OYC)

Material for Fourth Quarter of the Spring Semester 2011: Lecture 66-75 (29-38 of OYC)

Course Mechanics

Goals of Chem 125

Material from the first quarter of the Spring Semester 2011

Lecture 38 (1/10/11 ; OYC Lecture 1)
Lecture 38 timed (ppt) Audio (wma)
Lecture 38 movie with sound (mov)
Reaction Rates: Mechanism of Radical-Chain Halogenation, Bond Dissociation Energies, Information from Reaction Order
(2010 Lecture 38 ppt) (2010 Audio wma)

optional rate-limiting-step practice

Lecture 39 (1/12/11 ; OYC Lecture 2)
Lecture 39 timed (ppt) Audio (wma)
Lecture 39 movie with sound (mov)
Fractional and Inverse Rate Laws, Bond Dissociation Energies, Radical-Chain Halogenation, Reactivity-Selectivity "Principle"
(Lecture 39 ppt)
(2010 Audio wma)

Lecture 40 (1/14/11 ; OYC Lecture 3)
 Lecture 40 timed (ppt) Audio (wma) Lecture 40 movie with sound (mov)
Reactivity-Selectivity; Radical Addition of HBr; Rates of Chain Reactions
(Lecture 40 ppt)
(2010 Audio wma part 1wma part 2 sorry for interruption)

NOTE:  Problems for Wednesday 1/19/11 on slides 5 & 18 of Lecture 40 ppt

Lecture 41 (1/19/11 ; OYC Lecture 4)
Lecture 41 timed (ppt) Audio (wma)
Lecture 41 movie with sound (mov)
Fractional-Order Rate Laws Revisited; Electronegativity & Bond Strength; Solvation
(Lecture 41 ppt) (2010 Audio wma)

Lecture 42 (1/21/11 ; OYC Lecture 5)
Lecture 42 timed (ppt) Audio (wma)
Lecture 42 movie with sound (mov)
Lecture 42-2011 with rotating nonactin (zip)
Solvation & H-Bonding; Ionophores; Solvent Influence on Acidity

(Lecture 42 2010 ppt)  (2010 Audio wma)

Lecture 43 (1/24/11 ; OYC Lecture 6)
Lecture 43 timed (ppt) Audio (wma) Lecture 43 movie with sound (mov)
Brønsted Acidity; Nucleophilic Substitution 
(Lecture 43 2010 ppt (2010 Audio wma)

Your answer to the pKa problem in Frame 14 need not be turned in, but it may be relevant later
Here are links to the the pKa Table of Ripkin and Evans
and to the Penn State pKaTable

Lecture 44 (1/26/11 ; OYC Lecture 7)
Lecture 44 timed (ppt) Audio (wma)
Lecture 44 movie with sound (mov)
Nucleophilic Substitution Tools - Stereochemistry, Rate Law, Substrate, Nucleophile, Leaving Group
(Lecture 44 2010 ppt)  (2010 Audio wma)

Lecture 45 (1/28/11 ; OYC Lecture 8
Lecture 45 timed (ppt) Audio (wma) Lecture 45 movie with sound (mov)
Solvent, Leaving Group, Bridgehead Substitution, Pentavalent Carbon?
(Lecture 45 2010 ppt)  (2010 Audio wma)

Supplementary Reading:
Pentavalent Carbon and "Proving" the SN2 Mechanism
optional - Nucleophilicity, Basicity, and Linear Free Energy Correlations

Lecture 46 (1/31/11 ; OYC Lecture 9
Lecture 46 timed (ppt) Audio (wma) Lecture 46 movie with sound (mov)
Pentavalent Carbon? E2, SN1, E1
(Lecture 46 2010 ppt)   (2010 Audio wma)

Lecture 47 (2/2/11 ; OYC Lecture 10)
Lecture 47 timed (ppt) Audio (wma)
Lecture 47 movie with sound (mov)
SN2, E2, SN1, E1: an Instructive Project.  Alkenes: Stability and Addition Mechanisms
Note: Friday's exam covers through Frame 19 of the powerpoint

There will be a review session Wednesday evening 8-10 PM, Room 117 WLH for Friday's Exam.


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 2/9/07 (pdf)        Exam 5 2007 Answers (pdf)
Exam 5 2010 (pdf)        Exam 5 2010 Answers (pdf)

Exam 5 2011 (pdf)   Exam 5 2011 Preliminary Answer Key (pdf)
Material from the second quarter of the Spring Semester 2009

Lecture 47 (2/2/11 ; OYC Lecture 10)
Lecture 47 timed (ppt) Audio (wma) Lecture 47 movie with sound (mov)
Alkenes: Stability and Addition Mechanisms
Note: Beginning with Frame 21 of the powerpoint for the second quarter
2010 Lecture by J. S. Siegel: Addition to Alkenes - A Synthetic Chemist's Perspective
(Lecture 47 ppt)   (2010 Audio wma)

Lecture 48 (2/7/11 ; OYC Lecture 11)
Lecture 48 timed (ppt) Audio (wma)
Lecture 48 movie with sound (mov)
note: C-H energy in slide 3 has been corrected
 Alkenes: Stability and Addition Mechanisms; Electrophilic Addition 
(Lecture 48 ppt)   (2010 Audio wma)

Lecture 49 (2/9/11 ; OYC Lecture 12)
Lecture 49 timed (ppt) Audio (wma)
Lecture 49 movie with sound (mov)
Electrophilic Addition to Alkenes with Nucleophilic Participation
Halonium, Carbenes, Hydroboration/Oxidation

(Lecture 49 ppt)   (2010 Audio wma)

Lecture 50 (2/11/11 ; OYC Lecture 13)
Lecture 50 timed (ppt) Audio (wma)
Lecture 50 movie with sound (mov)
More Electrophilic/Nucleophilic Addition: Carbenoids, Epoxidation/Epoxides
(Lecture 50 ppt )  (2010 Audio wma)

Lecture 51 (2/14/11 ; OYC Lecture 14)
Lecture 51 timed (ppt) Audio (wma)
Lecture 51 movie with sound (mov)
More Addition to Alkenes: Ozonolysis & Acetal Hydrolysis; Dipolar Cycloaddition; CH3Li + H2C=O
( Lecture 51 ppt) (2010 Audio wma)

Lecture 52 (2/16/11 ; OYC Lecture 15)
Lecture 52 timed (ppt) Audio (wma)
Lecture 52 movie with sound (mov)
Organometallic Reagents, Catalysts, Polymerization; Addition by Radicals & Electrophilic Carbon; Rubber Balls
( Lecture 52 ppt) (2010 Audio mov) (2010 Audio mp3)
N.B. .mov and .mp3 formats. Note the audience comment following 42:00.

Lecture 53 (2/18/11 ; OYC Lecture 16)
Lecture 53 timed (ppt) Audio (wma)
Lecture 53 movie with sound (mov)
Isoprenoids; Tuning Polymer Properties
( Lecture 53 ppt) (2010 Audio wma)

Lecture 54 (2/21/11 ; OYC Lecture 17)
Lecture 54 timed (ppt) Audio (wma)
Lecture 54 movie with sound (mov)
Alkynes.  Linear and Cyclic Conjugation: Allylic Intermediates, Dienes
( Lecture 54 ppt) (2010 Audio wma)
See replacement for frame 5 here:  NBS allylic bromination

Lecture 55 (2/23/11 ; OYC Lecture 18)
Lecture 55 (ppt) Audio (wma) Lecture 55 movie with sound (mov)
Dienes vs. Intermediates.  Theory: 4n+2 Aromaticity
( Lecture 55 ppt) (2010 Audio wma)

McBride Review Session for Monday Exam
 8-10 PM, Wednesday 2/23/11  Room 117 WLH

Exam Monday, February 28
Room 160 SCL 10:30-11:30
or Room 111 SCL 10:15-11:15

Practice for Monday'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 2011)
Exam 6 2006 (pdf)   
(sorry no answer key)
Exam 5 2009 (pdf)  Answers(pdf) (Questions 1,2,4 relevant for 2011)
Exam 6 2010 (pdf)     2010 Answers (pdf)

Exam 6 2011 (pdf)
Exam 6 2011 Answer key (pdf) citations to lectures

Material from the third quarter of the Spring Semester 2011

Lecture 56 (2/25/11 ; OYC Lecture 19)
Lecture 56 timed (ppt) Lecture 56 Movie with sound (mov)
Cycloaddition, Electrocyclic Reactions; Dewar Benzene,
(Lecture 56 ppt)  (2010 Audio wma)
Lecture 57 (3/2/11 ; OYC Lecture 20)
Lecture 57 timed (ppt
or pptx) Lecture 57 package (zipped with audio & animation) Lecture 57 Movie with sound (mov)
Spectroscopy: ψ(t), Atoms, n-pi*, (Lindlar); IR: mixing and independence of local modes, Hydrocarbon chains
(Lecture 57 ppt)
 (2010 Audio wma)

Lecture 58 (3/4/11 ; OYC Lecture 21)
Lecture 58 package (zipped with movies) (timed ppt only
or pptx) (audio wma only) Lecture 58 Movie with sound (mov)
Alkane-Alkene-Alkyne; C=O; "Practical" IR spectroscopy.  NMR introduction: Precession
(Lecture 58 ppt  (2010 Audio wma)
Precession Page Problems

Lecture 59 (3/21/11 ; OYC Lecture 22)
Lecture 59 timed (ppt
or pptx) Audio (wma) Lecture 59 Movie with sound (mov)
MRI; NMR: Peak Integration, Chemical Shift 
(Lecture 59 ppt)
 (2010 Audio wma)

Lecture 60 (3/23/11 ; OYC Lecture 23)
Lecture 60 timed (ppt
or pptx) (Audio wma) Lecture 60 Movie with sound (mov)
NMR: Diamagnetic Anisotropy, Spin-Spin Splitting, Isotropic J
(Lecture 60 ppt)  (2010 Audio wma)

Lecture 61 (3/25/11 ; OYC Lecture 24)
Lecture 61 timed (ppt or pptx) (Audio wma) Lecture 61 Movie with sound (mov)
problems have been repaired in both pptx and mov files.  Let me know if there are others.
NMR: Higher-Order Effects, Dynamics
(Lecture 61 ppt)  (2010 Audio wma)

Lecture 62 (3/28/11 ; OYC Lecture 25)
Lecture 62 timed (ppt or pptx) (Audio wma) Lecture 62 Movie with sound (mov)
NMR: Decoupling, C13, Correlation (Dilute Double Labeling and 2D NMR); Electrophilic Aromatic Substitution
(Lecture 62 ppt)  (2010 Audio wma)

Lecture 63 (3/30/11 ; OYC Lecture 26)
Lecture 63 timed (ppt or pptx) (Audio wma) Lecture 63 Movie with sound (mov)
Friedel-Crafts, Diazonium Utility, Synthesis Problems, Nucleophilic Aromatic Substitution, Benzylic Stabilization, 
(2010 Lecture 63 ppt)  (2010 Audio wma)

Lecture 64 (4/1/11 ; OYC Lecture 27)
Lecture 64 timed (ppt or pptx) (Audio wma) Lecture 64 Movie with sound (mov)
Triphenylmethyl and US Chemistry; C=O Groups - Overview
(Lecture 64 ppt) (2010 Audio wma)

Lecture 65 (4/4/11 ; OYC Lecture 28)
Lecture 65 timed (ppt or pptx) (Audio wma) Lecture 65 Movie with sound (mov)
C=O Groups - Acid and Base Catalysis, Equilibrium, Protecting Groups, Imines
(Lecture 65 ppt)  (2010 Audio wma)

Sample questions for 7th Exam (Wednesday, 4/6/2011):

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 7 2010 (pdf)  2010 Answers (pdf)

Exam Review:

Prof. McBride led a review sesson on Wednesday evening 4/6/11  (audio file for what its worth wma)
and here is the nmr powerpoint used in the review (ppt or pptx)

You may take the hour exam in SCL 160 at the normal class time or in SCL 111 at 10:15 am.

Exam 7 2011 (pdf)

Material from the fourth quarter of the Spring Semester 2011

Lecture 66 (4/6/11 ; OYC Lecture 29)
Lecture 66 timed (ppt or pptx) (Audio wma) Lecture 66 Movie with sound (mov)
Imines & Enamines; electron-transfer, Bookkeeping, Oxidizing/Reducing Reagents
(Lecture 66 ppt) (2010 Audio wma)

Latimer on Atomic Oxidation States

Lecture 67 (4/11/11 ; OYC Lecture 30)
Lecture 67 timed (ppt or pptx) (Audio wma) Lecture 67 Movie with sound (mov)
Triphenylmethyl Spectra & alpha,para-Dimer; Friedel Crafts Again; Oxidizing/Reducing Reagents
(Lecture 67 ppt) (2010 Audio wma)

Lecture 68 (4/13/11 ; OYC Lecture 31)
Lecture 68 timed (ppt or pptx) (Audio wma) Lecture 68 Movie with sound (mov)
HIO4 Cleavage; Alcohols/Grignard; Green Chemistry
(Lecture 68 ppt)  (2010 Audio wma)

Lecture 69 (4/15/11 ; OYC Lecture 32)
Preliminary Lecture 69 (ppt or pptx) Lecture 69 Movie with sound (mov)
Guest Lecture by Prof. G. B. Ellison (Univ. of Colorado)
How Bond Strengths are Measured

Lecture 70 (4/18/11 ; OYC Lecture 33)
Lecture 70 timed (ppt or pptx)
(Audio wma) Lecture 70 Movie with sound (mov)
(the mov file has been edited to remove a few errors)
Mitsunobu Reaction, Acids and Acid Derivatives
(Lecture 68 ppt)  (2010 Audio wma) and (Lecture 69 ppt)  (2010 Audio wma)

Lecture 71 (4/20/10 ; OYC Lecture 34)
Lecture 71 almost timed (ppt or pptx) (Audio wma)  Lecture 71 Movie with sound (mov)
Acids and Acid Derivatives
(Lecture 70 ppt)  (2010 Audio wma)

Lecture 72 (4/22/11 ; OYC Lecture 35)
Lecture 72 timed (ppt or pptx)
(Audio wma)  Lecture 72 Movie with sound (mov)
Acyl Insertions, alpha-Reactivity

 Lecture 73 (4/25/11 ; OYC Lecture 36)
Lecture 73 timed (ppt or pptx)
(Audio wma)  Lecture 73 Movie with sound (mov)
alpha Reactivity and Condensations; Carbohydrates -  Introduction to Fischer's Proof of the Configuration of Glucose
(2010 guest lecture(s) by Prof. Ziegler - Lecture 72 ppt)  (2010 Audio wma)

The Szombathy-Soxhelet Extractor
(give the student some credit)

What Fischer actually said: Translation of Fischer Proof pdf

Lecture 74 (4/27/11 ; OYC Lecture 37)
Lecture 74 timed (ppt or pptx) Audio (wma) Lecture 74 Movie with sound (mov)
(Lecture 73 ppt)
frames 5 and 8 corrected
(2010 Audio wma)
Fischer Glucose Proof; Synthesis of an Unnatural Product (Anti-Aromatic Cyclobutadiene in a Clamshell)

Lecture 75 (4/29/11
; OYC Lecture 38)
Lecture 75
timed (ppt or pptx) Audio (wma) Lecture 75 Movie with sound (mov)
(Lecture 74 ppt)  (2010 Audio wma)
Review: Synthesis of a Natural Product (Woodward's Synthesis of Cortisone)

Review Session (5/2/11)
2011 Audio (wma)
blackboard photos will be coming later (perhaps this evening)

there is also a recording of the last year's review session and some of the graphics
(2010 Audio wma)  (ppt)  
(At 1:21:50 in the 2010 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.

Remaining Help Sessions 2011:
(to be confirmed by e-mails from the leaders)

 Sunday (May 1) WLH 114, 7-9pm, Peer Tutors

Tuesday (May 3) WLH 211, 7-9pm, Phillip

Thursday (May 5) 
WLH 211, 7-9pm, Jon

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
Spring Final 2010.pdf

Friday (May 6, 2011) 9am-12noon  Room 59 SPL (Sloan Physics lecture room)

Spring Final 2011.pdf

revised to here 2011

Other things you might enjoy (after studying for the final):

Lecture from last year on material not covered this year:

Lecture 72b (4/26/10)
follow-up guest lecture(s) by Prof. Ziegler
We will not be doing this topic in 2011 (any more that we have already done it)
(Lect 72b ppt) (2010 Audio wma)
A second lecture in which Prof. Ziegler discusses ring isomers (pyranose, furanose) and dimers (disaccharides) of sugars and how their structures were proven is optional.  It will NOT be covered on the 2011 final exam.

Another Example of Synthesis:
Fancy, informative website describing the synthesis of another natural product, Taxol, a complex natural product used in treating breast and ovarian cancer.  Again
this topic will NOT be covered on the 2011 final exam.

HDYK - SillimanCTW - Silliman


copyright 2009,10,11  J. M. McBride