CHEMISTRY 332
SYLLABUS
FALL 2012
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
s-zhang@wiu.edu
Currens Hall 430-B
(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 315. Laboratory meets on Thursday
(11:00 AM- 1:50 PM Sec 22; 2:00 PM- 4:00 PM Sec 21) 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
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Topic Coverage for CHEM 332
Week
Title of Chapter
1
Alcohols and Ethers
Aug 20-24
(11)
2
Alcohols and Ethers
Aug 27-31
(11)
3
Oxidation-reduction and
Sept 4-7
organometallic compounds
(12)
4
Oxidation-reduction and
Sept 10-14
organometallic compounds
(12)
5
Conjugated system and
Sept 17-21
aromatic compounds
(13, 14))
6
Aromatic reactions (15)
Sept 24-28
7
Oct 1-5
8
Oct 8-11
9
Oct 15-19
10
Oct 22-26
11
Oct 29-Nov 2
Topics
Synthesis of alcohols from alkenes, reactions of
alcohols, conversion of alcohol into leaving groups
Synthesis of ethers, reactions of ethers, reactions
of epoxides
Oxidation of alcohols, reduction of carbonyl
compounds
Preparation and reactions of Grignard, alkyllithium
and cuprates reagents
Conjugation, resonance theory, electron
delocalization, allylic substitution, 1,4-addition,
Diels-Alder reaction, Huckel’s rule
Electrophilic aromatic substitution (EAS),
activating/deactivating substituents direction
effects
Aromatic reactions (15)
Nucleophilic aromatic substitution, additionelimination mechanism, benzyne mechanism,
preparation and reactions of aromatic diazonium
salts
Aldehydes and ketones (16) Synthesis of aldehydes and ketones
Aldehydes and ketones (16) Nucleophilic addition to C=O
Carboxylic acids and their
derivatives (17)
Carboxylic acids and their
derivatives (17)
12
Nov 5-9
Enols and enolates (18)
13
Nov 12-16
14
Nov 19-23
15
Nov 26-30
16
Dec 3-7
17
Dec 12
Enols and enolates
condensation reactions (19)
Thanksgiving break
Enols and enolates
condensation reactions (19)
Chemistry of life (22-25)
Final Exam
Nucleophilic addition-elimination at the acyl
carbon, preparation of carboxylic acids
Inter-conversions of carboxylic acids and their
derivatives,
preparation of polyesters and polyamides
Formation of enols and enolates, halogenations of
carbonyl compounds at  carbon, alkylation of
carbonyl compounds at  carbon
Aldol reactions, Claisen condensation
Conjugate addition, Robinson annulations,
Mannich reaction
Introduction of carbohydrates, amino acids and
proteins, nuleic acids
1:00-2:50 pm
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
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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
Quiz 1
Quiz 2
Quiz 3
Exam 1
Quiz 4
Quiz 5
Quiz 6
Exam 2
Quiz 7
Quiz 8
Quiz 9
Quiz 10
Exam 3
Quiz 11
Quiz 12
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
15
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)
Final Examination
Quizzes (15 pts x 10)
Problem set (20 pts x 5)
Attendance
Lab Grade
TOTAL
Letter Grade
%Points (+)
300 pts
150 pts
150 pts
100 pts
50 pts
250 pts
1000
% Points (-)
3
A
B
C
D
F
Useful Resources:
>85 - <80
>70 - <67
>60 - <57
Less than 50
100-90
>80 - <75
>67 - <64
>57 - <54
>90 - <85
>75 - <70
>64 - <60
>54 - <50
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 Policies:
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)
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
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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.
Laboratory Information:
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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.
List of Experiments and grading (250 pts) for CHEM 332 lab
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Week
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
Experiment
No lab
Lab check-in; Multi-step sequence synthesis: Conversion of benzaldehyde to
benzoin and oxidation of benzoin to benzil (Exp 36)
Multi-step sequence synthesis (continued): Conversion of benzaldehyde to
benzoin and oxidation of benzoin to benzil
Preparation and reaction chemistry of Grignard reagent phenylmagnesium
bromide (Exp 38)
(Synthesis project #1 report due at the beginning of the lab, 40 pts)
Preparation and reaction chemistry of Grignard reagent phenylmagnesium
bromide
Organic qualitative analysis: identification of unknown compound #1
(Synthesis project report #2 due at the beginning of the lab, 40 pts)
Organic qualitative analysis: identification of unknown compound #1
(Lab take-home quiz #1 due at the beginning of the lab, 10 pts)
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)
Organic qualitative analysis: identification of unknown compound #2
(Lab take-home quiz #2 due at the beginning of the lab, 10 pts)
Organic qualitative analysis: identification of unknown compound #3
(Unknown #2 report due at the beginning of the lab, 20 pts)
Organic qualitative analysis: identification of unknown compound #3
(Lab take-home quiz #3 due at the beginning of the lab, 10 pts)
Organic qualitative analysis: identification of unknown compound #4a & 4b
(Unknown #3 report due at the beginning of the lab, 20 pts)
Organic qualitative analysis: identification of unknown compound #4a & 4b
Thanksgiving break
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)
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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