FA20 233 Syllabus G - Coursework PDF

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CHEM 233 • Organic Chemistry I Laboratory • Fall 2020 Course Syllabus Course Information Title: CHEM 233, Organic Chemistry Laboratory I, Basic organic techniques (distillation, crystallization), reactions (esterification, oxidation, addition, substitution, elimination), instruments (gas and liquid chromatography). CRN: (see below) Course Credit hours: 2 Prerequisites: Credit or concurrent registration in CHEM 232 Registration: Students must enroll in one Lab Section: Sections A

Sections B

11518 21604 11523 11549 11537 11529 11540

Time

TA

Room

TA email

M, 8:00 – 11.50 am

Van Vu Maxim Radzhabov

2SEL 3030

[email protected]

2SEL 3030

[email protected]

M, 12:00 – 3:50 pm

Laura Alonso

2SEL 3030

[email protected]

M, 12:00 – 3:50 pm

Xua Hu

2SEL 3030

[email protected]

T, 8:00 – 11.50 am

Mario Noboa

2SEL 3030

[email protected]

T, 12:00 – 3:50 pm

Robert Zhang

2SEL 3030

[email protected]

2SEL 3030

[email protected]

2SEL 3030

[email protected]

2SEL 3030

[email protected]

2SEL 3030

[email protected]

M, 8:00 – 11.50 am

W, 8:00 – 11.50 am 21605

11546

W, 8:00 – 11.50 am W, 12:00 – 3:50 pm

11547 11541 11542 11473 11508 11502 11544

W, 12:00 – 3:50 pm

Jesba Ban Concepcion Siyuan Su Sebastian Marquez Alexakos Panagiotis

R, 8:00 – 11.50 am

Xuan Duong

2SEL 3030

[email protected]

R, 12:00 – 3:50 pm

Mihir Chavda

2SEL 3030

[email protected]

F, 8:00 – 11.50 am

Daniel Sotelo

2SEL 3030

[email protected]

F, 8:00 – 11.50 am

Haoran Zhu

2SEL 3030

[email protected]

F, 12:00 – 3:50 pm

Ryan Hippman

2SEL 3030

[email protected]

F, 12:00 – 3:50 pm

Maxim Radzhabov

2SEL 3030

[email protected]

Instructor Information Instructor: Dr. Maria Yermolina Email: [email protected] Office: SELW 2206A Office hours: TBA

Course Material Required: Experimental Organic Chemistry: A Miniscale and Macroscale Approach, Gilbert & Martin, 6th Edition (but 4th and 5th Edition may also be used) Organic Chemistry Laboratory Manual, Landrie, McQuade & Yermolina 10th Edition Chemistry Lab Notebook – 100 pages (http://www.hmpublishing.com/products/ organicchemistry-spiral-bound.html), ISBN 978-1-930882-46-1) Chemistry Splash Goggles (must seal completely around face) Website The UIC Blackboard web system will be used as the course website (http://blackboard.uic.edu). Website material will be updated throughout the semester, including notices, this syllabus, instructor & TA information, and pre-lab notes. Course Description & Objectives CHEM 233 is divided into two complementary parts. In Part One, students will learn the theories and principles of isolation, purification, characterization, and compositional analysis of organic molecules through techniques such as thin-layer and column chromatography, gas chromatography, infrared spectroscopy, melting point, and distillation. These laboratories provide the foundation for Part Two of the course, in which students will learn the techniques of various chemical reactions that are relevant to organic synthesis. Each experiment in Part Two typically involves one functional group transformation. These objectives are summarized in the dehydration of 2-methyl-2-butanol (lab 8) by sulfuric acid (Figure 0.1). In this instance, the reaction technique is relatively straightforward: add 6 M sulfuric acid and heat. The isolation of the alkenes is obtained by fractional distillation, which was explored during Part One of the course. At this point, each student will have isolated a clear liquid, which of itself has no pedagogical value. The justification for performing the reaction is realized in the steps that follow. Chemical tests, which frequently involve visual evidence such as color changes or precipitation, are employed in this example to support the presence of alkenes. The clear liquid now has identity, an alkene, indicating successful reaction techniques to cause the functional group transformation. Analysis of the liquid by gas chromatography, however, shows that it is actually a mixture of alkenes. By comparing the retention times in the gas chromatograph with the retention times of known alkenes, the composition of the mixture can be reasonably deduced. Additionally, the relative ratio of each alkene can be determined by integration and normalization of the spectral peaks. Finally, students will use the chemical theory taught in this course and in CHEM 232 to explain their process and justify their results by answering questions such as: • • • •

Why was 6 M sulfuric acid use instead of 18 M? Under what principles does fractional distillation operate? What are the mechanisms that account for the formation of each alkene? What is a reasonable explanation for the ratio of alkenes observed by GC?

OH

Reaction

H2SO4 Δ

Purification & Isolation

Fractional Distillation

+

Compositional Analysis

Chemical Theory

The alkenes are separated by gas chromatography. Integration of the resulting peaks allows for calculation of the relative ratios of each product

Based on the mechanism of elimination, explain the relative ratio of alkenes obtained

Characterization Confirm the presence of the new alkene functional group using the Baeyer & Bromine tests for unsaturation

Baeyer Test HO C C

+

MnO4-

C

OH C

+

H2 O alkene

vicinal diol (colorless)

permanganate (purple)

MnO2

manganese dioxide (brown)

Bromine Test Br C C

+

C

Br2 CH2Cl2

alkene

bromine (orange)

C Br vicinal dihalide (colorless)

Course Manual, TAs, and Class Structure A primary requirement for success in this course is student preparation. Because most of the work will be completed individually, with a minimal amount of formal lecture instruction, each student must study and understand the required readings and techniques prior to completing each experiment. Poor planning often results in longer experiment times, which may prevent the completion of the laboratory by the end of class. The topics for review for each experiment, as well as the textbook page numbers where they can be found (for the 6th, 5th and 4th Edition of the textbook), are listed in the manual accompanying this syllabus. The manual will also include questions to use as study material, material to cover in the lab report, and procedural notes for most (but not all) experiments. The course manual provided to you contains your required reading assignments, study questions, laboratory procedures, procedural notes, cautions, supplementary information, pre-lab slides, and lab report discussion suggestions. For some labs it also contains worksheets that you may need to complete prior to, during, or after the lab. You are responsible for thoroughly reading the required material in your

textbook and in the course manual before you complete the lab. Several of the topics covered in this course may not have been covered in CHEM 232, so your preparation is essential to your success. Your preparedness will be judged by your participation in class discussions and your ability to complete the labs within the given time frame. Each laboratory session will begin with a pre-lab quiz. These quizzes are made up of five multiple-choice questions that come from the assigned background reading, pre-lab slides, and procedure for that day’s experiment. The quiz begins precisely at the start of lab and lasts five minutes. Students who come late to lab will not be able to make up the quiz. After the pre-lab quiz, your TA will give a 10-15-minute lecture briefly covering the general theory and techniques for each experiment, as well as provide a demonstration of the relevant techniques if necessary. During this time, your TA may also announce procedural changes or warnings that have not been outlined in the course manual. Your attendance during this period is essential to ensure that you are well-informed an well-protected. Therefore, students who are excessively late (> 15 minutes) will not be allowed to participate in that lab and will receive a zero. You are required to keep a lab notebook to record your observations and data during the experiment. This is also a good place to write down, prior to the lab, an experimental procedure you intend to follow. A guide to keeping a laboratory notebook is provided in the course manual, as is a grading rubric and example lab report. Following each lab you will write a lab report according to the criteria outlined in the rubric and course manual. This report is due the next class period. When grading the lab reports, each TA is required to maintain as close to a 70% average a possible with a 15% standard deviation in grades (the spread of grades). Lab reports will be assessed a two-point penalty for each day that they are late (including weekends). Your TA will be available for a minimum of 2 h/week to help you with your questions. TAs will provide their office hours during the first week of class. All office hours are held in the Science Learning Center (SES 3510). If your TA cannot answer your questions or if you have a particular concern about the course, please see your instructor during office hours. I particularly encourage you to speak with me if you believe that you or other members of your section are being taught or graded unfairly or in a manner inconsistent with the course objectives and policies outlined in this syllabus. Very little can be done at the end of the semester to rectify wrongs that took place many weeks before. Finally, a lab practical exam will be given at the end of the semester and assessed by your TA and the instructor according to a rubric written by the instructor in this manual and on Blackboard. This practical is meant to assess your laboratory skills and techniques that were learned and developed throughout the semester, as well as your ability to prepare for a lab given a procedure in advance.

Assessment Task

Points

# Task/Semester

Total Points

Pre-lab

5

10

50

Laboratory Reports

20

10

200

Midterm Exam

100

1

100

Practical Exam

100

1

100

Final Exam

100

1

100

TOTAL

550

Pre-lab (50 points): The pre-lab write-ups (5 points each) must be submitted to Blackboard prior to the start of lab. Each TA will grade pre-labs according to the rubric established by the instructor, which is found on the Blackboard site for this course. Laboratory Reports (200 points): Ten laboratory reports (20 points each), on each experiment undertaken in this course. These reports are graded by the TAs according to a rubric written by the instructor. This rubric is found on the Blackboard site for this course. All lab reports must be submitted on Blackboard site under the Lab Report Submission (Safe Assign) tab before the start of a lab session. Lab reports will be assessed a two-point penalty for each day that they are late (including weekends). No additional time will be given to submit your work if you miss the deadline. Midterm Exam (100 points): Covering the theory and techniques of the laboratory experiments. The exam is written and graded by the instructor of the course and will closely resemble the homework assigned. Practical Exam (100 points): Students will synthesize and demonstrate the chemiluminescence of luminol in the laboratory. This practical exam will be assessed and graded by the instructor and TA. More information, as well as a grading rubric, is found in the course manual and on the Blackboard site for this course. Final exam (100 points): Covering the theory and techniques taught in the course. The concepts covered in the lab practical exam will NOT be on the final exam. All Exams will be given via Respondus! You have to download (free) Respondus BEFORE the class starts. All instructions on how to download Respondus can be found under Course Content.

Normalization of Laboratory Reports If there are large variations in lab report scores between sections, and these variations do not seem to reflect the normal differences in student performance, the instructor may normalize each section’s lab report scores to a ~70% average or higher and a ~15% standard deviation or lower. Students should best judge their performance in the course by frequently checking the Blackboard webpage, asking their TA or the instructor for their section’s average and standard deviation and comparing those values with their own. Undoubtedly, each section will display a different level of performance. Therefore, if normalization is determined to be necessary, the average of all written exams for each section will be used to determine the normalized lab score. Course Curve/Grade Cut-offs A: 85-100% B: 75-84.9% C: 65-74.9% D: 55-64.9% F: 54.9% or lower

University Policies Student tips for midterm grades: http://tigger.uic.edu/depts/oaa/advising/student_midterm.html Disability Services: http://www.uic.edu/depts/oar/campus_policies/disability_notification.html “Concerning disabled students, the University of Illinois at Chicago is committed to maintaining a barrierfree environment so that individuals with disabilities can fully access programs, courses, services, and activities at UIC. Students with disabilities who require accommodations for full access and participation in UIC Programs must be registered with the Disability Resource Center (DRC). Please contact DRC at (312) 413-2183 (voice) or (312) 413- 0123 (TDD).” – From above UIC website, accessed 01/01/2014

Religious Holidays: http://www.uic.edu/depts/oae/docs/ReligiousHolidaysFY20132015.pdf http://www.uic.edu/ucat/catalog/ARE.shtml#w “The faculty of the University of Illinois at Chicago shall make every effort to avoid scheduling examinations or requiring that student projects be turned in or completed on religious holidays. Students who wish to observe their religious holidays shall notify the faculty member by the tenth day of the semester of the date when they will be absent unless the religious holiday is observed on or before the tenth day of the semester. In such cases, the students shall notify the faculty member at least five days in advance of the date when he/she will be absent. The faculty member shall make every reasonable effort to honor the request, not penalize the student for missing the class, and if an examination or project is due during the absence, give the student an exam or assignment equivalent to the one completed by those students in attendance. If the student feels aggrieved, he/she may request remedy through the campus grievance procedure.” - UIC Senate Policy on religious holidays (approved May 25, 1988) Non-Discrimination Policy: http://www.uic.edu/depts/oaa/disability_resources/nondiscrimination.html “The University of Illinois will not engage in discrimination or harassment against any person because of race, color, [sex,] religion, national origin, ancestry, age, marital status, disability, sexual orientation including gender identity, unfavorable discharge from the military or status as a protected veteran and will comply with all federal and state nondiscrimination, equal opportunity and affirmative action laws, orders and regulations. This nondiscrimination policy applies to admissions, employment, access to and treatment in the University programs and activities.” – From above UIC website, accessed 01/01/2014 Student Disciplinary Policy: http://www.uic.edu/depts/dos/docs/Student%20Disciplinary%20Policy%202011-12%20Final-1.pdf Academic Dishonesty http://www.uic.edu/depts/dos/studentconduct.html “As an academic community, the University of Illinois at Chicago is committed to providing an environment in which research, learning, and scholarship can flourish and in which all endeavors are guided by academic and professional integrity. All members of the campus community—students, staff, faculty, administrators— share the responsibility of insuring that these standards are upheld so that such an environment exists. Instances of academic misconduct by students, and as defined herein, shall be handled pursuant to the Student Disciplinary Policy.” – From above UIC website, accessed 01/01/2014 According to the UIC Undergraduate Catalogue, 2011-2013, academic dishonesty includes: “Cheating”: Either intentionally using or attempting to use unauthorized materials, information, people, or study aids in any academic exercise, or extending to or receiving any kind of unauthorized assistance on any examination or assignment to or from another person. Fabrication: Knowing or unauthorized falsification, reproduction, lack of attribution, or invention of any information or citation in an academic exercise. Facilitating Academic Dishonesty/Plagiarism: Intentionally or knowingly representing the words or ideas of another as one’s own in any academic exercise. Bribes, Favors, Threats: Bribing or attempting to bribe, promising favors to or making threats against, any person, with the intention of affecting a record of a grade, grade, or evaluation of academic performance. Any conspiracy with another person who then takes or attempts to take action on behalf or at the direction of the student. Examination by Proxy: Taking or attempting to take an exam for someone else other than the student is a violation by both the student enrolled in the course and the proxy or substitute. Grade Tampering: Any unauthorized attempt to change, actual change of, or alteration of grades or any tampering with grades.

Non-original Works: Submission or attempt to submit any written work authored, in whole or part, by someone other than the student.” – accessed 01/01/2014 NOTE: This list is not all-inclusive! Any student caught engaging in academic dishonesty will be subject to the UIC Academic Disciplinary Policy and will receive a grade of F in the course. Lab Policies 1. Goggles & Masks: It is prohibited to work in the laboratory without approved (must seal completely around eyes) safety goggles and a mask according to state laws. First-, second, and third-time offenses will result in the loss of 10 points, the lowering of the final score by one letter grade, and the dismissal from the course with a grade of F, respectively. Students who forget their goggles or their mask will not be allowed to participate. 2. Missed Lab: There are no make up labs! No labs may be missed, skipped, or made up in other sections. If you missed the lab you have to use the data provided and submit the lab report according to schedule for your section. 3. Pre-Labs: The pre-lab portion of the lab must be completed prior to the start of lab and submitted on Blackboard under Course Content – Pre-Lab Submission. Students will have 2 attempts to submit their pre-lab. Pre-labs not submitted on time will receive zero points. No additional time will be given to submit your work if you miss the deadline. 4. Lab Reports: Lab reports are due the next class period and must be submitted to Blackboard before to the start of the lab session. Late reports will be assessed a two-point penalty for each day they are late (including weekends...