CHEMISTRY 202
ORGANIC CHEMISTRY II
Spring Semester, 2013

Instructor: William A. Price, Ph.D.
Office: Holroyd 345
Phone: 951-1261
price@lasalle.edu

Teaching Schedule

Texts:

Lecture:

McMurry, John, Organic Chemistry, 8th Edition, Brooks/Cole, Pacific Grove, CA 2012.

Organic Chemistry Direct McMurry's companion website

Laboratory:

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:

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

Grades:
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:

Strategy:
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 one’s 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 instructor’s 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

aromatic nomenclature

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

classical nomenclature

well known carboxylic acids

overview good summary of carboxylic acids: acidity and preparation

carboxylic acids and acid chlorides reactions

CH 21 Carboxylic Acid Deriviative

nitriles

nomenclature some problems answers

hydrolysis and Fischer esterification

interesting acid derivatives fats, nylon, and flavors

GHB fyi

CH 20-21 practice exam Q's / answers

CH 22 Alpha Substitutions and Condensations

overview

acidity alpha to carbonyl

alpha halogenation

ethyl acetoacetate and diethyl malonate rxns

alkylation via enolate and enamine

aldol condensation

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

Office Hours:
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.