CHEMISTRY 202
ORGANIC CHEMISTRY II
Summer Session II, 2018

Monday - Thursday
June 27 - August 3, 2018

Holroyd room 355


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

Syllabus

Lecture Schedule

Laboratory Schedule

Laboratory Syllabus

Lab Report Rubric


Texts:

Lecture:

Wade, L.G., Simek, J.W., Organic Chemistry, 9th Edition, Pearson, Boston, MA 2017.

Sapling for Homework: Here is a direct link to your course site: La Salle University - CHM 202 - Summer18 - PRICE

Please direct your students to go www.saplinglearning.com/login to log in or create an account. The following link includes detailed instructions on how to register for your course: https://community.macmillan.com/docs/DOC-5972-sapling-learning-registering-for-courses .

During sign up or throughout the term, if you have any technical problems or system questions please fill out the support request form, located in the College Student Support Community, https://community.macmillan.com/community/digital-product-support/college-students-support-community , for direct assistance.

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. In the summer, you will need to work at the course every day of the session as the typical 15-week semester is compressed to five weeks. Keeping up is most readily accomplished by reading the appropriate chapter prior to attending class. Keep a copy of the detailed lab and lecture schedules so that you know when things are due. Your ability to focus and be organized is absolutely crucial. 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, Homework & Chapter Coverage:
The lecture portion of your grade will be determined by your performance on four hourly examinations (400 pts), homework (Sapling; 100 pts), and quizzes (100 pts). We will cover chapters 10-22 in CHM 202. Chapter coverage will be selective. It is the student's responsibility to know what portions of chapters are not covered in lectures and thus not covered on exams.

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 should use a composition notebook for problems). The problems at the end of the chapters are excellent and can be used to fine tune your grasp of the material. You will also find many tutorials, practice problems from old exams on the website.

Sapling:

A schedule of homework problems can be found upon enrolling in Sapling. There will be several problem sets assigned throughout the semester. They will be posted roughly a week before they are due. These may take up to two hours to complete so do not start them at the last minute. You can save your work and come back to it at a later time. A very important new skill that you will continue to use is the ability to draw molecules using the template drawing tools supplied in pertinant questions. The first week , if you haven't already done so, The first week, if you haven't already done so , you should do the modules on “Drawing Tips”, “Curved Arrow Overview” and “Stereochemistry Training” so that you are familiar with nuances like subscripts, superscripts, drawing Lewis structures and structures of more elaborate organic molecules (sometimes in 3 dimensions), etc. After the due dates, the problems sets will remain open, but are closed to further credit.

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 50%
Sapling HW 75 pts 9.4%
Quizzes 120 pts 15.6%
Laboratory 200 pts 25%
Total 800 pts 100%

Final Grades:

Assessment of your performance on the various assignments will culminate in a letter grade (I do use +/- grade system).

Typically, a letter grade of A = 90-100; B = 80-89.9; C = 70-79.9; D = 60-69.9; F < 60.

Missed exams can only be made up with documentation for the absence and a note from your academic advisor.

This syllabus is a guide and every effort will be made to adhere to the contents. However, circumstances and events may make it necessary to modify the syllabus slightly during the semester depending on the progress made and needs of the students. Any changes will be made with plenty of advanced notice.

Below, you will find all of the powerpoint slides that will be used in this course. Occasionally, a sequence of slides will be skipped and those will not be covered on exams. You will also find links to problem sets, tutorials and other explanatory worksheets.

CH 10 Alcohols - Structure and Synthesis - ppt slides

CH 11 Reactions of Alcohols - ppt slides

QUIZ 1 practice from Spring, 2014

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 from spring, 2014

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