ORGANIC CHEMISTRY II
Spring Semester, 2013
Instructor: William A. Price, Ph.D.
Office: Holroyd 345
McMurry, John, Organic Chemistry, 8th Edition, Brooks/Cole, Pacific Grove, CA 2012.
Organic Chemistry Direct McMurry's companion website
J. R. Mohrig, C.N. Hammond, P.F. Schatz and T.C. Morrill, CHL 201-202 Laboratory Manual from Modern Projects and Experiments in Organic Chemistry, W.H. Freeman Custom Publishing, New York, 2010.
J.R. Mohrig, C.N. Hammond and P.F. Schatz, Techniques in Organic Chemistry, Third Edition, W.H. Freeman and Company, New York, 2010.
Alternatively for lab:
Mohrig, J.R., Hammond, Schatz, P.F. and Morrill, T.C., Modern Projects and
Experiments in Organic Chemistry, Freeman, New York, 2003.
Course Description and Objectives:
Chemistry 202 is a course that will build on the foundation that was established in CHM 201. The course will begin with the study of conjugated pi systems including pericyclic reactions and aromatic (benzene-type) chemistry. After a brief look at ultraviolet (UV) spectroscopy, we will re-focus on structure elucidation using infrared (IR) and nuclear magnetic resonance (NMR) spectroscopy. Take a look at some excellent tutorials and spectroscopy resources on my LINKS page. The course will continue with examination of structure, preparation, and reactivity of oxygen-containing functional groups within molecules. The approach used will incorporate orbital analysis (structure), electron distribution and flow (mechanism), reactions, and ultimately synthesis.
The amount of material to be covered is quite large, thus it is necessary that you keep up with the course lecture to lecture. This is most readily accomplished by reading the appropriate chapter prior to attending class. This way, the material covered in class will seem somewhat familiar (what a great feeling) and will hopefully clarify any questions you might have. Do all of the recommended chapter problems in McMurry. Do not hesitate to ask questions in class, after class or during any office hour. Use of the study guide is helpful, but only if you first attempt the problems on your own.
Suggested Problems from McMurry, 7th edition
Suggested problems from McMurry, 8th edition
Examinations, Quizzes & Chapter Coverage:
The lecture portion of your grade will be determined by your performance on four hourly examinations (400 pts), 4 short quizzes and/or homework (100 pts) and the cumulative final examination (150 pts). Hour exams will be given every tenth lecture with the following chapter coverage:
|Exam I||Wednesday, February 6||Chapters 14,15,16|
|Exam II||Friday, March 1||Chapters 12, 13,17|
|Exam III||Friday, April 5||Chapters 18,19,20|
|Exam IV||Wednesday, May 1||Chapters 21,22,23|
Quizzes (in-class or take-home) will be given midway between examinations: January 28 (M), February 20 (W), March 22 (F), and April 17 (W)
2012-2013 La Salle Academic Calendar
The course consists of both lecture (75%) and laboratory (25%). One cannot pass the course without passing both the lecture and the laboratory. The laboratory grade is determined solely by the laboratory instructor. Your final grade will be determined on your total number of earned points relative to those of your colleagues:
|4 Hourly Exams||400 pts||47%|
|4 Quizzes||100 pts||12%|
|Final Exam||150 pts||18%|
As is evident by the ambitious examination schedule, it is important that you keep pace with this course. It is well documented that attempting to cram three weeks of material into a day and a half prior to an exam is an unsuccessful method to studying in this course. Rewriting ones notes after each lecture is an effective way to reinforce the lecture material and it typically brings questions to the surface. Attendance will not be taken regularly, but consistent lecture attendance is strongly urged since examinations reflect the instructors emphasis in class.
The text contains an excellent set of problems. It is recommended that you solve the problems in the running text as you read the material (you may want to use a composition notebook for problems). Recommended problems will be suggested at the end of the chapters and can be used to fine tune your grasp of the material.
Chemistry By Design A very good website that describes syntheses of a huge number of biologically significant componds, from University of Arizona
CH 14 Conjugated Dienes ppt
Chapter 14-15 practice problems / answers
Conjugation, MO Theory, and Pericyclic Reactions from Vanderbilt, this is a terrific overview
Introduction to M.O. Theory from Carey, a good interactive site
CH 15 Benzene & Aromaticity ppt
Bonding in Benzene a very good description of the Kekule description of benzene
Vioxx Problem, answer
M.O.'s of benzene, cyclobutadiene
CH 16 Chemistry of Benzene ppt
Chapter 16 practice problems / answers
more Chapter 16 E.A.S. rxns / answers
Aromatic side chain reactions
Nucleophilic Aromatic Substitution and Benzyne mechanistic explanations
Practice Exam I
Some spectroscopy links
CH 12 Infrared Spectroscopy - ppt slides
Mass Spectrometry - ppt slides
Mass spectrometry tutorial from the University of Arizona
IR/mass matching problems - mass spec answers
IR & Mass spec. powerpoint tutorial L.G. Wade
IR analysis tutor from UCLA
IR overview with problems excellent site from Michigan State, good explanations and problems
Spectroscopy overview IR, UV-vis, mass and NMR with problems from MSU
Mass Spectrometry problem set due 2/18/13 Answers
CH 13 Nuclear Magnetic Resonance Spectroscopy - ppt slides
NMR background, theory and essentials - from Michigan State U.
spin-spin splitting slides for both C-13 and proton NMR
Structure Elucidation Workbook very good spectral problems with IR, NMR & mass spec., Notre Dame
answers to "green" combined spectroscopy problems from Notre Dame site (see above)
Spectral problems 10 problems with IR, mass, proton and C-13 NMR, from Carey
NMR overview site with H-1 and combined H-1/C-13 NMR problems from Central Connecticut State
Spectroscopy problems from MSU, proton and carbon-13 NMR with IR
1H NMR problem set / Answers
Combined spectroscopy problems
Exam II question 8 - to be turned in 3/1/13 at the exam
CH 17 Alcohols - ppt slides
Reactions of Alcohols ppt slides
Chapter 17 Problems / answers
CH 18 Ethers: makin' em and breakin' em - ppt slides
epoxide ring-opening from chapter 18
CH 17-18 practice exam Q's / Answers
Practice exam III (CH 17-18) / answers
CH 19 Ketones and Aldehydes ppt slides
Practice Problems from Chapter 19 / answers
Exam III practice class handout
CH 20 Carboxylic Acids
CH 19 and 20 Problems
well known carboxylic acids
overview good summary of carboxylic acids: acidity and preparation
carboxylic acids and acid chlorides reactions
CH 21 Carboxylic Acid Deriviative
nomenclature some problems answers
hydrolysis and Fischer esterification
acid derivatives fats, nylon, and flavors
interesting acid derivatives fats, nylon, and flavors
CH 20-21 practice exam Q's / answers
CH 22 Alpha Substitutions and Condensations
acidity alpha to carbonyl
ethyl acetoacetate and diethyl malonate rxns
alkylation via enolate and enamine
FINAL EXAM PRACTICE
Francis Carey's Organic Chemistry text has associated with it an excellent help site that I highly recommend. Topics are listed on the home page.
Click here to access Frank Carey's excellent site
I am available Monday, Wednesday and Friday from 9:30-11:00 and at other times by appointment. Please take advantage of these times to clarify any
lecture or laboratory material. My schedule for the semester is here so that finding me will be easier.