Course Instructor:Dr. Shaozhong Zhang Currens Hall 430-B

CHEMISTRY 332SyllabusFall 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.

(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

Topic Coverage for CHEM 332

Week / Title of Chapter / Topics
1
Aug 20-24 / Alcohols and Ethers
(11) / Synthesis of alcohols from alkenes, reactions of alcohols, conversion of alcohol into leaving groups
2
Aug 27-31 / Alcohols and Ethers
(11) / Synthesis of ethers, reactions of ethers, reactions of epoxides
3
Sept 4-7 / Oxidation-reduction and organometallic compounds (12) / Oxidation of alcohols, reduction of carbonyl compounds
4
Sept 10-14 / Oxidation-reduction and organometallic compounds (12) / Preparation and reactions of Grignard, alkyllithium and cuprates reagents
5
Sept 17-21 / Conjugated system and aromatic compounds
(13, 14)) / Conjugation, resonance theory, electron delocalization, allylic substitution, 1,4-addition, Diels-Alder reaction, Huckel’s rule
6
Sept 24-28 / Aromatic reactions (15) / Electrophilic aromatic substitution (EAS), activating/deactivating substituents direction effects
7
Oct 1-5 / Aromatic reactions (15) / Nucleophilic aromatic substitution, addition-elimination mechanism, benzyne mechanism, preparation and reactions of aromatic diazonium salts
8
Oct 8-11 / Aldehydes and ketones (16) / Synthesis of aldehydes and ketones
9
Oct 15-19 / Aldehydes and ketones (16) / Nucleophilic addition to C=O
10
Oct 22-26 / Carboxylic acids and their derivatives (17) / Nucleophilic addition-elimination at the acyl carbon, preparation of carboxylic acids
11
Oct 29-Nov 2 / Carboxylic acids and their derivatives (17) / Inter-conversions of carboxylic acids and their derivatives,
preparation of polyesters and polyamides
12
Nov 5-9 / Enols and enolates (18) / Formation of enols and enolates, halogenations of carbonyl compounds at  carbon, alkylation of carbonyl compounds at  carbon
13
Nov 12-16 / Enols and enolates condensation reactions (19) / Aldol reactions, Claisen condensation
14
Nov 19-23 / Thanksgiving break
15
Nov 26-30 / Enols and enolates condensation reactions (19) / Conjugate addition, Robinson annulations, Mannich reaction
16
Dec 3-7 / Chemistry of life (22-25) / Introduction of carbohydrates, amino acids and proteins, nuleic acids
17
Dec 12 / Final Exam / 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 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

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: (absence policy)

(academic integrity policy)

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 (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.

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.

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)