CHEM 330, ELEMENTS OF ORGANIC CHEMISTRY

Western Illinois University, Fall 2016

Instructor: Dr. Jin Jin, Currens Hall 430-A (email: ) (phone 298-2261)

Lecture: 9:00-9:50 am; M, W, Th, F in Currens 203; Lab: Tuesday in Currens 423

Office Hours: MWF (10:00 – 11:30 AM) or by Appointment

Textbook and materials:

Introduction to Organic Chemistry (5th Edition) by Brown & Poon (ISBN-13: 978-1118-083383)) (Required)

Laboratory Manual: Organic Chemistry, A Short Course by David Hart, Leslie Crane, Harold Hart and T. K. Vinod (ISBN-13: 978-1111425845) (Required)

Laboratory Notebook (Required)

Safety glasses (Required)

Course Description: A one-semester introduction to organic chemistry. Coverage includes nomenclature of compounds, study of selected reactions and mechanisms, spectroscopy and study of biologically relevant molecules such as carbohydrates, amino acids, and proteins. Does not count toward chemistry major.

Pre-Requisite:
CHEM 202 (C grade or better).

Grading:

Quizzes (10) 250 Points

Exams (3) 300 Points

Laboratory 250 Points

Final Exam Comprehensive 200 Points

Total 1000 Points

Grading Scheme

Total Points Letter Grade

1

930-1000 A

900-929 A-

870-899 B+

840-869 B

800-839 B-

770-799 C+

740-769 C

700-739 C-

650-699 D+

600-649 D

500-599 D-

0 - 499 F

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LECTURE TESTS AND QUIZZES

Three lecture exams (each worth 100 points), ten quizzes (each worth 25 points), and a comprehensive final exam worth 200 points will be given. Make-up quizzes and make up exam will be given for those with excused absences. Only two make-up quizzes and one make-up exam will be allowed. Excused absences are defined as documented illnesses, military service requirements, and family emergencies. All excused absences must be approved by the course instructor.

Homework: Since critical thinking and problem solving are important components of chemistry, homework will be assigned regularly and posted in WesternOnline in order to help students grasp principles and concepts discussed in class. Regular practice will help your overall exam scores.

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.

Studying Tips: Organic chemistry is often perceived as a very difficult course. Unless you keep pace with the presented material, the course will undoubtedly be extremely challenging and stress-inducing for you. The course work is cumulative and will become increasingly difficult as the semester progresses. DO NOT FALL BEHIND!

Make sure you come to lecture prepared. This means reading through the material we will cover in class before you arrive. The best way to accomplish this is through a two-step process. Quickly (10 minutes) scan the section you are reading. After familiarizing yourself with the section reread it in more detail (45 minutes), taking a few notes on the way. It is also necessary to reread the section after lecture to reinforce the concepts or to clarify any difficult material.

Do Not become frustrated if you do not understand a topic the first time it is presented. I encourage you to ask questions during lecture and office hours.

Do Not wait until the week of the exam to begin studying. The easiest and wisest way to approach the course is to study and practice problems a few hours each day. Ask for help if you need it, my office will typically have an open door feel free to drop in or send me an email. The success in organic chemistry is through reading, learning, doing problems and understanding.

C or better statement: “In accordance with Illinois State Board of Education certification rules, all candidates seeking teacher certification are required by Western Illinois University to obtain a grade of “C” or better in all directed general education course, all core courses, and all courses in the option. Note: A “C- ” is below a “C”.”

Web Resources: The course homepage is on the Western Online. Information for this class will be posted there, including the course syllabus, homework problem sets, quizzes, exams, their answers and your grades. Any class announcements will also be posted here.

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.

Students with disabilities : In accordance with University values and disability law, students with disabilities may request academic accommodations where there are aspects of a course that result in barriers to inclusion or accurate assessment of achievement. To file an official request for disability-related accommodations, please contact the Disability Resource Center at 309-298-2512, or in 143 Memorial Hall. Please notify the instructor as soon as possible to ensure that this course is accessible to you in a timely manner.

University values, Title IX, and other federal and state laws prohibit sex discrimination, including sexual assault/misconduct, dating/domestic violence, and stalking. If you, or someone you know, has been the victim of any of these offenses, we encourage you to report this to the Title IX Coordinator at 309-298-1977 or anonymously online at: http://www.wiu.edu/equal_opportunity_and_access/request_form/index.php. If you disclose an incident to a faculty member, the faculty member must notify the Title IX Coordinator. The complete Title IX policy is available at: http://www.wiu.edu/vpas/policies/titleIX.php.

Web address for student rights and responsibilities: http://www.wiu.edu/provost/students.php

Web address for Academic Integrity Policy: http://www.wiu.edu/policies/acintegrity.php

Tentative Lecture Schedule

Week / Topic / Concepts Covered
1
8/22-8/26 /
Chapter 1: Covalent Bonding and Shapes of Molecules
/ Bonding, hybridization, shapes of molecules, bond angle, bond lengths, resonance, common functional groups
2
8/29-9/2 / Chapter 2: Acids and Bases / Acids and bases,
pKa value, structure and acidity, Lewis acids and bases, electromagnetic spectrum, infra-red spectroscopy, recording and analyzing IR spectra, correlation table
3
9/5-9/9 / Chapter 3: Alkanes and Cycloalkanes / Alkanes, cycloalkanes, nomenclature, conformations and cis-trans isomerism in cycloalkanes,
conformations of cycloalkanes
4
9/12-9/16 /
Chapter 4: Alkenes and Alkynes
/ alkenes and alkynes, nomenclature, cis-trans isomerism, E/Z nomenclature, dienes and trienes
5
9/19-9/23 / Chapter 5: Reactions of Alkenes and Alkynes / Reactions of alkenes, electrophilic additions(addition of HX, H2O, Br2 etc) Markovnikov rule
6
9/26-9/30 / Chapter 6: Chirality / Stereochemistry, Chirality, enantiomers, Racemic mixture, meso compounds
7
10/3-10/7 / Chapter 7: Haloalkanes / Alkyl halides, nomenclature, SN1 and SN2 reactions, mechanisms,
Factors controlling SN1 and SN2 reactions, elimination reactions, substitution vs elimination
8
10/10-10/14 /
Chapter 8: Alcohols, Ethers, and Thiols
/ Reactions of alcohols, use of organometallic reagents for the synthesis of, dehydration reactions
9
10/17-10/21 /
Chapter 9: Benzene and Its Derivatives
/ Structure of benzene, electrophilic substitution reactions, mechanisms of nitration, bromination and alkylation/acylation reactions
10
10/24-10/28 / Chapter 11: Infrared Spectroscopy / infra-red spectroscopy, recording and analyzing IR spectra, correlation table
11
10/31-11/4 / Chapter 12: Nuclear Magnetic Resonance Spectroscopy / nuclear magnetic resonance spectroscopy (1H and 13C NMR)
12
11/7-11/11 / Chapter 13: Aldehyes and Ketones / Aldehydes and ketones, nomenclature, reactions with Grignard reagents, reduction and oxidation reactions
13
11/14-11/18 /
Chapter 14: Carboxylic Acids
/ Carboxylic acids, properties and reactions
14
11/21-11/25 /
Thanksgiving break
15
11/28-12/2 / Chapter 15: Functional Derivatives of Carboxylic acids / Carboxylic acid derivatives
16
12/5-12/9 /

Introduction to Carbohydrates, proteins and nucleic acids (Chapter 18-20)

Review

/ Introduction to chemistry of life
17
12/12-12/16 / Final Exam (comprehensive) / Dec 14, 8:00-9:50 am

Tentative Schedule of Exams and Quizzes: CHEM 330

Assessment / Week
Quiz 1 / 2
Quiz 2 / 3
Quiz 3 / 4
Quiz 4 / 5
Exam 1 (chpt 1-5) / 6
Quiz 5 / 7
Quiz 6 / 8
Quiz 7 / 9
Exam 2 (chpt 6-9) / 10
Quiz 8 / 11
Quiz 9 / 12
Exam 3 (chpt 11-14) / 15
Quiz 10 / 16

CHEM 330 Lab

Western Illinois University, Fall 2016

Lab Coordinator: Dr. Jin Jin, Currens Hall 430-A (email: ) (phone: 298-2261)

Laboratory meeting time and place

Sec 218:00-10:50 am Tu Cu 423

Sec 222:00-4:50 pmTu Cu 423

Lab manual and required materials

  1. Laboratory Manual: Organic Chemistry, A Short Course by David Hart, Leslie Crane, Harold Hart and T. K. Vinod (ISBN-13: 978-1111425845)
  2. Laboratory Notebook

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.

Grading: The instructors will collaborate so as to grade each lab section in a uniform manner. Overall, the lab will count as 250 points and it will be added to your lecture portion points to tabulate a final grade for this course. Failure to complete the lab with at least 60% (>150 points out of 250 lab grade) will result in failure for the Lab. Since the laboratory experience is integral to the overall course, failure to earn a passing grade in the lab will result in an automatic failure for the course.

Laboratory Information

Hands-on experience is a vital factor in learning chemistry. The emphasis of the laboratory exercises will be on microscale methods and techniques. The laboratory grade will be based upon your completion of the experiments, lab reports and technique evaluation. 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.

Cleaning up. When you have finished your lab work, clean up your personal workspace by putting away your equipment, wiping or sweeping up spilled materials, disposing of waste chemicals in the proper containers in the waste hood, etc. Community areas (especially the instrument areas) are to be cleaned up immediately after you have used them. This would include the balances, the mp apparatus and used capillaries, the infrared cells, and the IR sample prep area.

Lab Reports: At the beginning of the next lab section, you must submit a lab report packet for the previous lab. The report packet should include prelab exercise (from lab manual), lab report (from lab manual), post-lab questions (from lab manual), lab notebook recordings (teared off from your lab notebook), and spectra obtained during the experiment. Lab notebook recordings should include the title of the experiment, a brief procedure, observation from the lab, result & discussion and conclusion. Sample of the lab notebook recording can be found the course website. Record all information in ink! They should be stapled together and handed in.

Grading Scheme

Prelab
Exercise
(lab manual) / Lab report
(lab manual) / Postlab questions
(lab manual) / Lab Notebook
(title, brief procedure, observation,
Result & discussion, conclusion) / Subtotal / Lab final exam / Total
5 / 5 / 5 / 5 / 20x10=200 / 50 / 250

Tentative Laboratory Schedule

Week / Expt # in Lab Manual / Topic and concepts covered
1
8/22-8/26 / No Lab
2
8/29-9/2 / Lab check-in
Laboratory Safety rules
3
9/5-9/9 / Expt #2 / Recrystallization: Purification of crystalline organic compounds
Solubility, crystallization, % recovery, melting point determination
4
9/12-9/16 / Expt #4 / Extraction: A Separation and isolation technique
Extraction, extraction coefficient, acid-base chemistry, use of drying agent, recrystallization, mp determination
5
9/19-9/23 / Expt #5 / Isolation of natural products: Caffeine and Eugenol
Stream distillation, IR spectroscopy
6
9/26-9/30 / Expt #6 / Chromatography
Chromatography, column chromatography, thin-layer chromatography, Rf values
7
10/3-10/7 / Handout posted on western online / Stereochemistry dry lab worksheet
8
10/10-10/14 / Expt #13 / Alkyl halides: Structure and reactivity in nucleophilic substitutions
SN1 and SN2 reaction mechanisms.
9
10/17-10/21 / Expt #8 / Preparation of alkenes from cycloalkanol and test for unsaturation
Distillation, Gas chromatography, % yield calculation.
10
10/24-10/28 / Expt #11 / Electrophilic aromatic substitution
% yield calculation, mp determination, IR and 1H NMR,
11
10/31-11/4 / No lab this week
12
11/7-11/11 / Handout posted on western online / NMR dry lab worksheet
13
11/14-11/18 / Expt #17 / Oxidation of aldehyde to carboxylic acid
Green chemistry, IR
14
11/21-11/25 / Thanksgiving Break
15
11/28-12/2 / Expt #29 / Make-up Lab period
Fats and oils; Soaps and detergents
16
12/5-12/9 / Laboratory Final Exam and Check-out

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