CHEMISTRY 202
ORGANIC CHEMISTRY II
Spring Semester, 2014


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

Teaching Schedule

CHM 202 Syllabus


Texts:

Lecture:

Wade, L.G., Organic Chemistry, 8th Edition, Pearson, Boston, MA 2013.

MasteringChemistry: Organic Chemistry II, CHM 202; Course ID: CHM202PRICE2014 Access code comes bundled with text in bookstore - to purchase separately, go to masteringchemistry link above.

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 alchohols, their synthesis and reactions. It is important to recognize that much of this continues the substitution and elimination concepts from the fall semester. We will then 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 then continue with the study of different functional groups in cluding ethers and epoxides, followed by conjugated pi systems including pericyclic reactions and aromatic (benzene-type) chemistry. After a brief look at ultraviolet (UV) spectroscopy, 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.

Examinations, Quizzes, Homework & Chapter Coverage:
The lecture portion of your grade will be determined by your performance on four hourly examinations (400 pts), 4 take-home quizzes and homework (MC) (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 5 Chapters 10-12.12
Exam II Friday, February 28 Chapters 12.13-15
Exam III Monday, March 31 Chapters 16-18
Exam IV Wednesday, April 30 Chapters 19-22

Quizzes (take-home) will be given midway between examinations: January 22 (W), February 17 (M), March 19 (W), and April 11 (F)

2013-2014 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:

4 Hourly Exams 400 pts 47%
4 Quizzes and HW 100 pts 12%
Final Exam 150 pts 18%
Laboratory 200 pts 23%
Total 850 pts 100%

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 10 Alcohols - Structure and Synthesis - ppt slides

CH 11 Reactions of Alcohols - ppt slides

QUIZ 1 due Jan 31, 2014 at 11AM

Chapter 11 Problems / answers

CH 12 Infrared Spectroscopy - ppt slides;

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

Mass Spectrometry - ppt slides

Mass spectrometry tutorial from the University of Arizona

Mass Spectrometry problem set ; Answers

IR/mass matching problems - mass spec answers

CH 13 Nuclear Magnetic Resonance Spectroscopy - ppt slides

Some spectroscopy links

Spectroscopy overview IR, UV-vis, mass and NMR with problems from MSU

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) - available from instructor

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

CH 14 Ethers: makin' em and breakin' em - ppt slides

epoxide ring-opening from chapter 14

CH 15 Conjugated Systems ppt slides

EXAM II Take-home question due 2/28/14 at noon

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 16 Benzene & Aromaticity ppt slides

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 17 Chemistry of Benzene ppt slides

Chapter 16 practice problems / answers

more Chapter 16 E.A.S. rxns / answers

Aromatic side chain reactions

Nucleophilic Aromatic Substitution and Benzyne mechanistic explanations

CH 18 Ketones and Aldehydes ppt slides

Practice Problems from Chapter 18 / answers

CH 19 Amines

CH 20 Carboxylic Acids

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.