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CHEMISTRY 332 SYLLABUS FALL 2011
Course Description: A study of nomenclature, preparations, reactions, and reaction
mechanisms of the functional groups of aliphatic and aromatic compounds. Prerequisite: CHEM
331 (C grade or better, strictly enforced). 3 hrs. lect.; 3 hrs. lab.
Course Instructor: Dr. Shaozhong Zhang Currens Hall 430-B
s-zhang@wiu.edu (309)298-1685
Attendance: You are expected to attend class regularly and punctually. Excessive absences
will be reported to the financial aid office. If you anticipate or suffer an absence by emergency
or tragedy, it may be possible to make up missed work. Notify the course instructor at the
earliest opportunity. Students who are called away from the campus to participate in University
sponsored trips such as athletics or professional meeting may be allowed to make up missed
work if the student provides a signed memo from the faculty sponsor. Attendance is taken as 50
points out of 1000 total points as shown in the grading portion.
Required Texts & Materials:
Organic Chemistry (10th Edition) by Solomons & Fryhle
Introduction to Organic Laboratory Techniques: A Microscale Approach
by Pavia, Lampman, Kriz, and Engel
Laboratory Notebook (Carbonless Copy Sheets, Required)
Meeting Times: 1:00 pm-1:50 PM; M,W,F in Currens 202. Laboratory meets on Thursday
(2:00 PM- 4:50 PM) in Currens 431.
Office Hours: Monday, Wednesday, Friday 10:00 AM-11:30 AM or by appointment
Course Objectives:
To know and understand the bonding, structure and reactivity of organic compounds
To appreciate the dependence of molecular properties on bonding and structure
To know the reactions and to understand the mechanisms by which those reactions take
place
To obtain the ability to carry out simple reactions and learn the process of chemical
synthesis
To learn spectroscopic and related techniques to determine the structure of organic
molecules
To gain practical laboratory experience in a modern organic chemistry laboratory setting
1
Topic Coverage for CHEM 332
Week Title of Chapter Topics
1 Alcohols and Ethers Synthesis of alcohols from alkenes, reactions of
Aug 22-26 (11) alcohols, conversion of alcohol into leaving groups
2 Alcohols and Ethers Synthesis of ethers, reactions of ethers, reactions
Aug 29-Sept (11) of epoxides
2
3 Oxidation-reduction and Oxidation of alcohols, reduction of carbonyl
Sept 5-9 organometallic compounds compounds
(12)
4 Oxidation-reduction and Preparation and reactions of Grignard, alkyllithium
Sept 12-16 organometallic compounds and cuprates reagents
(12)
5 Conjugated system and Conjugation, resonance theory, electron
Sept 19-23 aromatic compounds delocalization, allylic substitution, 1,4-addition,
(13, 14)) Diels-Alder reaction, Huckel’s rule
6 Aromatic reactions (15) Electrophilic aromatic substitution (EAS),
Sept 26-30 activating/deactivating substituents direction
effects
7 Aromatic reactions (15) Nucleophilic aromatic substitution, addition-
Oct 3-7 elimination mechanism, benzyne mechanism,
preparation and reactions of aromatic diazonium
salts
8 Aldehydes and ketones (16) Synthesis of aldehydes and ketones
Oct 10-14
9 Aldehydes and ketones (16) Nucleophilic addition to C=O
Oct 17-21
10 Carboxylic acids and their Nucleophilic addition-elimination at the acyl
Oct 24-28 derivatives (17) carbon, preparation of carboxylic acids
11 Carboxylic acids and their Inter-conversions of carboxylic acids and their
Oct 31-Nov 4 derivatives (17) derivatives,
preparation of polyesters and polyamides
12 Enols and enolates (18) Formation of enols and enolates, halogenations of
Nov 7-11 carbonyl compounds at carbon, alkylation of
carbonyl compounds at carbon
13 Enols and enolates Aldol reactions, Claisen condensation
Nov 14-18 condensation reactions (19)
14 Thanksgiving break
Nov 21-25
15 Enols and enolates Conjugate addition, Robinson annulations,
Nov 28-Dec condensation reactions (19) Mannich reaction
2
16 Chemistry of life (22-25) Introduction of carbohydrates, amino acids and
Dec 5-9 proteins, nuleic acids
17 Final Exam 1:00-2:50 pm
Dec 14
2
Quizzes & Exams: Twelve in-class quizzes (10-15 min. duration) will be administered during
the term and the “best ten” scores for the quizzes will be considered along
with other scores when assigning the final grade for the course. The other
two quizzes will be counted as your bonus points for the course. Students
will not be allowed MAKE-UP missed quizzes. In class exams will
consist of multiple choice questions as well as those requiring short
paragraph answers. Under no circumstance will a student be allowed
to make–up a missed exam without a doctor’s note indicating your
inability to attend class on the day of the exam.
The standardized American Chemical Society (ACS) test will be taken as the final exam. “Preparing for
your ACS examination in organic chemistry” is a suggested book to review for taking ACS exam. It can
be ordered online.
Schedule of Exams and Quizzes: CHEM 332
Assessment Week
Quiz 1 1
Quiz 2 2
Quiz 3 3
Exam 1 4
Quiz 4 5
Quiz 5 6
Quiz 6 7
Exam 2 8
Quiz 7 9
Quiz 8 10
Quiz 9 11
Quiz 10 12
Exam 3 13
Quiz 11 15
Quiz 12 16
Homework: Homework assignments will be provided on Western Online, and will not be distributed in
class. Due dates are posted on the top of all homework assignments. Five homework problem sets (20
pts each) will be given throughout the semester and are due at the beginning of class on their due date
(Homework assignment turned in late (for any reason) will have two point deducted per day;
Homework turned in two weeks after the due date will not be graded.). Each problem set is worth 20
points and will encompass material from your text and lecture. The problem sets will be designed to aid
in your understanding of the course material and act as an additional guide for test preparation.
Assessment
And Grading:
Lecture Examinations (100 pts x 3) 300 pts
Final Examination 150 pts
Quizzes (15 pts x 10) 150 pts
Problem set (20 pts x 5) 100 pts
Attendance 50 pts
Lab Grade 250 pts
TOTAL 1000
3
Letter Grade %Points (+) % Points (-)
A 100-90 >90 - <85
B >85 - <80 >80 - <75 >75 - <70
C >70 - <67 >67 - <64 >64 - <60
D >60 - <57 >57 - <54 >54 - <50
F Less than 50
Useful Resources: http://sdo.wiu.edu/facultyStaff/absencepolicy.asp (absence policy)
http://www.wiu.edu/policies/acintegrity.php (academic integrity policy)
http://sjp.wiu.edu/CodeOfConduct/index.asp (Disorderly conduct)
Emergency
Preparedness: WIU Office of Risk Management and Emergency Preparedness provides
resources on how to respond to emergency situations. Please view the video
resources at www.wiu.edu/rmep/ (Click “Resources” on the right side of the page)
WIU Policies: It is the policy of Western Illinois University to accommodate individuals with
disabilities pursuant to federal law and the University's commitment to equal
educational opportunities. It is the responsibility of the student to inform the
instructor of any necessary accommodations at the beginning of the course. Any
student with a disability requiring accommodations should contact the Office of
Disability Support Services.
Laboratory:
Laboratory safety rules
Wear safety goggles (eye protection) at all times when in the laboratory. This is a
departmental and state regulation.
Do not eat or drink in the laboratory.
Know the location and use of the nearest fire extinguisher, nearest First Aid kit, nearest
eye wash station, nearest safety shower, and nearest exit designated for evacuation.
You will be advised of the locations on the first day of the lab.
Know the location of the Material Safety Data Sheets ( MSDS) and know that you have
access to them. You are protected by the right to know law.
Know the NFPA (National Fire Protection Association) Hazardous Material Classification
Codes.
Report all accidents, even minor injuries, to the instructor at once.
In case of an organic chemical spilled on your person, flush with water, wash with soap,
rinse with water, rinse with ethyl alcohol, wash with soap, and rinse with water. Pat dry.
Never taste chemicals or solutions. Minimize the inhalation of organic vapors by using
the smallest amounts of materials and utilizing the hood as much as possible. Check the
MSDS if you have questions.
Dispose of all wastes properly. Read labels on bottles! Keep bench and floor clean.
Before leaving the laboratory, be sure that the water, steam, heaters, and gas cocks are
shut off.
4
Laboratory Information:
Hands-on experience is a vital factor in learning chemistry. Since the laboratory experience is
integral to the overall course, failure to earn a passing grade in the lab will result in
automatic failure for the course. Notebooks will be checked to verify that they contain the
information necessary for the day’s experiment. If a student comes to the lab with an incomplete
pre-lab report or does not seem to be prepared to do the work, that student will not be allowed
to continue in that day’s lab until the lab instructor is convinced of the student’s preparedness
for the experiment.
Lab Notebooks:
It is extremely important to keep a careful and complete record of the experiments in your
laboratory notebook. The laboratory notebook is a record of what happened in the experiment.
It should be understandable to others and should contain enough information such that the
experiment could be repeated at a later date by you or by someone else. Much of the notebook
will be data (descriptions, numbers, calculations, etc.), but a modicum of other information is
also required. Procedural information, changes in method or technique, etc. should be recorded
immediately, providing a complete narrative of everything you do as you are doing it. Therefore,
you will have to do a little writing before, during, and after each lab. A table of contents in your
notebook should also be kept current. Any graphs, computer print-outs, and spectra should be
attached in the notebook (taped or stapled) for a permanent record of the data.
In addition, I would ask for two additional protocols: 1. Leave the first few pages of the notebook
blank for a table of contents so that each experiment can be readily located. Pages should be
numbered consecutively. 2. Write your experimental plan on the left hand page in your
notebook, then record your observations and data on the right hand page.
A sample of recording lab notebook will be posted on WesternOnline. Lab notebook will
be collected twice for the whole semester (20 pts total).
Lab Reports:
The lab will consist of two parts this semester: Three synthesis projects and Identification of four
unknowns.
You will gain experience this semester with methods of identification and methods of separation
of a two-component mixture. You will identify three pure unknown compounds (#1-#3) and a
two-component unknown compounds (#4). You will write reports for all the four
identifications. Report format will be posted on WesternOnline. You will work
independently for identification of unknowns. Identification methods can be found in Part 4:
Identification of Organic Substances in PLKE lab manual and will be discussed in class.
The synthesis projects will be chosen from the designated projects which will be posted on
WesternOnline. You will also work independently for the synthesis projects. Each project will
consist of a two-step synthesis. You will write a scientific paper for each of the synthesis
project. The format and sample of the scientific paper will be posted on WesternOnline.
Late lab reports or problem sets will be deducted by 15% for each week. Lab
reports/Problems sets turned in two weeks after the due date will not be graded.
5
List of Experiments and grading (250 pts) for CHEM 332 lab
Week Experiment
1 No lab
2 Lab check-in; Multi-step sequence synthesis: Conversion of benzaldehyde to
benzoin and oxidation of benzoin to benzil (Exp 36)
3 Multi-step sequence synthesis (continued): Conversion of benzaldehyde to
benzoin and oxidation of benzoin to benzil
4 Preparation and reaction chemistry of Grignard reagent phenylmagnesium
bromide (Exp 38)
(Synthesis project #1 report due at the beginning of the lab, 40 pts)
5 Preparation and reaction chemistry of Grignard reagent phenylmagnesium
bromide
6 Organic qualitative analysis: identification of unknown compound #1
(Synthesis project report #2 due at the beginning of the lab, 40 pts)
7 Organic qualitative analysis: identification of unknown compound #1
(Lab take-home quiz #1 due at the beginning of the lab, 10 pts)
8 Organic qualitative analysis: identification of unknown compound #2
(Unknown #1 report due at beginning of the lab, 20 pts)
(lab notebook due at the end of the lab, 10 pts)
9 Organic qualitative analysis: identification of unknown compound #2
(Lab take-home quiz #2 due at the beginning of the lab, 10 pts)
10 Organic qualitative analysis: identification of unknown compound #3
(Unknown #2 report due at the beginning of the lab, 20 pts)
11 Organic qualitative analysis: identification of unknown compound #3
(Lab take-home quiz #3 due at the beginning of the lab, 10 pts)
12 Organic qualitative analysis: identification of unknown compound #4a & 4b
(Unknown #3 report due at the beginning of the lab, 20 pts)
13 Organic qualitative analysis: identification of unknown compound #4a & 4b
14 Thanksgiving break
15 Multi-step sequence synthesis: Preparation of N,N-diethyl-m-Toluamide-the insect
repellent “OFF” (Exp 47)
(Unknown #4 report due at the beginning of the lab, 20 pts)
16 Lab check out
(lab notebook due at the end of the lab, 10 pts)
(Synthesis project #3 report due, 40 pts)
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