CHEM 2210 Introductory Organic Chemistry PDF

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Download CHEM 2210 Introductory Organic Chemistry PDF

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CHEM 2210: Introductory Organic Chemistry I: Structure and Reactivity Course Outline Fall 2020

Sections: A01: MWF 11:30 – 12:20; A02: MWF 1:30 – 2:20; Note for 2020: All course content and lectures will be the same for both sections. This course will be delivered asynchronously and all lecture material will be available on UMLearn.

Instructor Information Lecture Dr. John Sorensen Email: [email protected] Telephone: 204-474-9504 Office hours: Check UM Learn

Dr. Rebecca Davis Email: [email protected] Telephone: 204-474-6252 Office hours: Check UM Learn

Laboratory Dr. Horace Luong Email: [email protected] Telephone: 204-474-7916 Office hours: Check UM Learn

Textbook and Required Material rd

Organic Chemistry 3 edition: David Klein, John Wiley & Sons Publishing. This textbook is available from the bookstore and comes bundled with “Organic Chemistry as a Second Language I & II” by David Klein as an additional resource. WileyPLUS on-line homework system (https://www.wileyplus.com/WileyCDA). The registration code for the on-line homework system comes bundled with the textbook. A stand-alone registration code is also available at the bookstore and comes bundled with a full electronic version of the textbook as well as the “Second Language” books. CHEM 2210 Laboratory Manual (2020 Edition)

Optional but Strongly Recommended Items Molecular Model Kit Molecular model kits are allowed/encouraged in all examinations and tests in this course. The bookstore has in stock the “Darling” model kits. Organic Chemistry 3rd edition, Student Study Guide and Solutions Manual, David Klein, The Solutions Manual is available in both hard copy and electronic version from the Bookstore.

General Outline The course consists of an introduction to the structure, bonding and functional groups of organic molecules. Included is a discussion of stereochemistry and the three-dimensional shape of organic molecules. The use of spectroscopic tools to determine molecular structure will cover primarily proton (1H) and carbon (13C) nuclear magnetic resonance spectroscopy. This material will be followed by a description of organic reaction mechanisms, and a number of common organic reaction types.

Grading Scheme Homework (WILEYPlus) Laboratory Work Mid-Term Test (2 hours, Oct. 30th) Final Examination (3 hrs; December exam period)

15 25 20 40

TOTAL

100

VW Policy: If you VW a course you will also be required to immediately withdraw from the lab. Therefore, students that VW a course will not be eligible for a lab exemption should they choose to re-take the course. On-line Homework: In order to help students in CHEM 2210 keep pace with the course material we are using an online homework system called Wiley PLUS. A series of assignments will be created in this environment to provide the opportunity to further explore the concepts discussed in lectures. Participation in the on-line homework is mandatory for full credit in CHEM 2210. The WileyPLUS registration code (at a discounted price) is available bundled with the textbook in the bookstore. A full price WileyPLUS registration code is available for students who do not wish to purchase the textbook. Mid-Term Exam: The mid-term test is scheduled for Friday, October 30 at 6:00-8:00 p.m. This exam will be delivered remotely. Final Examination: All students must write the final examination. The date for the final exam for CHEM 2210 is scheduled by the registrars’ office and will take place between December 12-23. Failure to write the final regularly scheduled examination without a valid medical certificate or compassionate reason will result in a mark of zero on the final examination (and a grade of F on the course). Final Grade: A total mark of greater than 55% is required for full credit in this course. Marks between 55% and 100% will be graded from C to A+. Students must obtain a grade of C (minimum 55%) or greater to proceed to either CHEM 2220 or CHEM/MBIO 2370. In order to obtain a passing grade in the course, you must earn a minimum 60% grade [9/15] on the laboratory work. Below is the formula used for calculating letter grades in CHEM 2210: Grade Point Value 4.5 4.0 3.5 3.0 2.5 2.0 1.0 0.0

Letter Grade

Numerical Score

A+ A B+ B C+ C D F

90.0 – 100 80.0 – 89.9 75.0 – 79.9 70.0 – 74.9 65.0 – 69.9 55.0 – 64.9 50.0 – 54.9 00.0 – 49.9

Review of Final Exam Script: The Faculty of Science has established a policy to permit students the opportunity to review their final exam script prior to the end of the Grade Appeal period. You must apply to view your exam during the predetermined viewing period. The Application Form can be obtained from the following link:

https://www.emailmeform.com/builder/form/J4j18ef01XkT9quo

CHEM 2210 Laboratory Please watch this video for an introduction to our lab program. Laboratories: Laboratory attendance is compulsory. Students in sections B01-B07 will attend the labs during the fall session while students in B81-B87 will attend labs in January. Students are divided into rotations where the first rotation will start the week of September 14, 2020. Please check UM Learn for rotation and locker assignment. All students registered in the laboratory must buy a CHEM 2210 laboratory manual (2020 Edition). Dr. Luong will be in contact with students in sections B81-B87 late fall on the lab scheduling for the critical hands-on activities period in January. Laboratory Safety: Lab coats and safety glasses or goggles must be worn at all times in the laboratory. Prescription glasses do not provide sufficient protection from chemical splashes; therefore, safety glasses or goggles must be worn over top of prescription glasses. Fully covered shoes and pants must be worn in the laboratory. Marking: A pre-lab iClicker quiz will be administered at the start of every laboratory period. Please ensure you have a registered iClicker remote or the app downloaded and registered on your devices when you come to the laboratory. Lab reports for all B01-B87 students will be due during the fall session. Lab report mark breakdowns are described in the lab manual. Late reports will be marked at a 1 mark/half hour deduction, up to one week (after which a grade of 0 will be applied). Lab reports are submitted online to UMLearn assignment folder. It is the student’s responsibility to submit reports to the correct dropbox. Grades for the reports are returned within 2 weeks at the latest. Exemptions: Laboratory exemptions will only be given if the lab has been successfully completed (i.e., receiving a minimum of 70% in the lab) between fall 2018-fall 2019. Student re-taking CHEM 2210 may apply for a laboratory exemption by completing the laboratory exemption form on the Department of Chemistry homepage. Students should also note that a lab exemption may be used only once by a student on repeating the CHEM 2210 course. Please note that the previously obtained lab mark will be used in the computation of your final mark in this course. Students who obtain a lab exemption based on study at an institution other than the University of Manitoba or for special case consideration will not have their lab mark used in the computation of their final mark.

Expectations Professional Conduct: We recognize that these are unusual circumstances, and that there are some adjustments needed when working virtually. At the same time, we do want to remind students that University policies, such as the Respectful Work and Learning Environment policy, still apply, as do basic expectations around how students will engage with each other, and with the University. This means that when participating in classes, online meetings, etc., students are expected to behave professionally, and follow the same basic norms as they would in person, such as being clothed, not being impaired, and participating respectfully. Essentially, if you wouldn’t do it in an in-person class, don’t do it in a virtual setting. Academic Integrity Plagiarism: Copying another student's examination, laboratory reports, or assignments, or an instructor's answer sheet from a previous year is plagiarism. Students quoting other sources of information in a laboratory report or other assignment must give proper credit. Plagiarism and other forms of cheating are prohibited. The full definition of plagiarism and the possible penalties associated with it are outlined in the General Calendar of the University. Cheating: The possession of unauthorized materials during an examination, including "crib notes" (whether hand- written or contained within a computer/calculator) or accessing online tutoring websites, is considered cheating and subject to action by the Student Disciplinary By Law. Calculators and text aids (books, notes, etc.) are NOT permitted in any term tests or examination. Students found with electronic devices or other unauthorized material during a chemistry examination will be given a grade of zero (0) on that examination and further penalties may apply. Faculty of Science Statement on Academic Misconduct: The Faculty of Science and The University of Manitoba regard acts of academic misconduct in quizzes, tests, examinations, laboratory reports or assignments as serious offences and may assess a variety of penalties depending on the nature of the offence. Acts of academic misconduct include, but are not limited to, bringing unauthorized materials into a test or exam, copying from another individual, using answers provided by tutors, plagiarism, and examination impersonation. Penalties that may apply, as provided for under the University of Manitoba's Student Discipline By-Law, range from a grade of zero for the assignment or examination, failure in the course, to expulsion from the University. The Student Discipline By-Law may be accessed at: http://umanitoba.ca/admin/governance/governing_documents/students/student_discipline.html All Faculty members (and their teaching assistants) have been instructed to be vigilant and report all incidents of academic misconduct to the Head of the Department.

Student Resources A list of University governing documents pertaining to students can be found here. Academic Resources: Various academic resources are available to students including the Science and Technology Library and various departmental help centers. Health & Mental Health Resources: Students with Health and/or Mental Health issues may seek advice and/or help from Student Counselling Center, Student Accessibility Services, and University Health Services. Copyright and Intellectual Property Resources: Copyrights and intellectual property must be respected by all students. For more information, please refer to the Copyright Office. Respectful Behavior Resources: Students are expected to act in a respectful manner. Policies regarding respectful work and learning environment and sexual assault can be found here. Final Examinations, Grades and Grade Appeals Resources: Final examination and grades policies can be found here.Students wishing to appeal their term work grade can do so through the Registrar’s office. A fee is charged for each appeal. Students wishing to view their final examination should go to the Department of Chemistry website and complete the final examination viewing form. Students wanting to appeal their final grade can initiate the process at the Registrar’s office. A fee will be charged for each appeal. See the Registrar’s office for more information. Limited Access and VW Resources: Students who fail or VW from a course will be subject to limited access to that course in future terms. That is, students will not be able to register for a course (for which they have VWed or failed) during the limited access registration period. For more information, please see the policy document for repeated courses.

CHEM 2210 Course Outline CHEM 2210 will be delivered asynchronously. Video lectures will be delivered in modules based on topic and not on a 50min lecture structure. All course material, including lecture videos, can be found on UMLearn. All Chapters and Sections are from Organic Chemistry 3rd Edition by Klein Chapter 1-2: Background reading and review only. This material is covered adequately in CHEM 1300 and CHEM 1310. ALSO: throughout CHEM 2210 IUPAC nomenclature of organic molecules will not be taught in lectures nor will it be explicitly examined. Students are expected to be able to draw a structure given a name and recognize a few common trivial names of molecules. Section 1: Structure and Bonding in Hydrocarbons Chapter 1: (As review 1.7 –1.10); Chapter 4: Entire Chapter The stability of alkanes and cycloalkanes will be illustrated with heat of combustion data. The conformations of alkanes will also be examined. The energy differences in the conformations of the cyclohexane chairs will be examined in detail and the effect of substitution on the equilibrium between non-degenerate chairs will be described.

Chapter 17: Aromatic Compounds Sections 17.1 – 17.5 The heat of hydrogenation of benzene will be used to illustrate the concept of aromaticity. A full molecular orbital description of the bonding in benzene will be used to help rationalize aromatic stabilization.

Section 2: Functional Groups Chapter 3; Entire Chapter Chapter 22: Sections 22.1 – 22.3; Chapter 12: Sections 12.1 – 12.2; Chapter 19: Sections 19.1 – 19.2; Chapter 20: Sections 20.1 – 20.3 This section will rationalize the chemistry of the functional groups. The structure, physical and chemical properties of common functional groups will be described. A description of alcohols and amines will be followed by a discussion of the chemistry of the carbonyl group. Carboxylic acids and their derivatives, such as esters and amides will be included in this section. A rationalization of the difference in the pKas of the various functional groups (including protons alpha to ester vs amide) will be described in this section.

Section 3: Spectroscopy – Structure elucidation Chapter 14: Entire chapter; Chapter 15: Entire chapter At the end of this section students will be able to deduce the structure of an organic molecule from a given set of spectroscopic data. The use of mass spectrometry will be introduced only as a means to determine the molecular weight of a molecule. Infrared (IR) spectroscopy will be described as a technique that gives an initial indication of functional groups. Both proton (1H) and carbon (13C) nuclear magnetic resonance will be described in detail, with an emphasis on the application to structure elucidation.

Section 4: Stereochemistry Chapter 5: Entire Chapter The 3-dimensional shape of organic molecules and the concept of chirality will be described. The concept of chirality will be introduced and the CIP system of assigning absolute configuration will be described. Optical activity will also be covered in this section. Molecules with more than one stereogenic center will also be described.

Section 5: Mechanisms of Organic Reactions Chapter 6: Entire Chapter A comparison of the uni- and bi-molecular substitution mechanisms and with analysis of the accompanying energy diagrams will be the focus of this section. The thermodynamic vs kinetic control of reactions will be described.

Chapter 10: Section 10.1 – 10.7 An introduction to radicals and radical halogenation will be used as an illustration of the Hammond postulate. The discussion will focus on “product-like” vs “reactant-like” transition states and the effect on regiochemistry. A brief discussion of the stereochemistry of halogenation as well as the outcome of allylic bromination will be included.

Section 6: Substitution and Elimination Reactions Chapter 7: Entire Chapter The use of substitution and elimination reactions for basic functional group interconversions will be introduced. Students will be able to distinguish between the substitution and elimination mechanisms and predict the products when given the starting material and conditions....