UNIVERSITY OF CALGARY FACULTY OF SCIENCE DEPARTMENT OF CHEMISTRY COURSE SYLLABUS WINTER 2018 EEEL 235A. Dr. Wendy Benoit

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1 1. Course: CHEMISTRY 351, Organic Chemistry I UNIVERSITY OF CALGARY FACULTY OF SCIENCE DEPARTMENT OF CHEMISTRY COURSE SYLLABUS WINTER 2018 LEC DAYS TIME ROOM INSTRUCTOR OFFICE OFFICE HOURS L01 MWF 10:00-10:50 EEEL 161 Dr. Wendy Benoit EEEL 235A wlbenoit@ucalgary.ca TBA Desire 2 Learn (D2L) : CHEM 351 L01 - (Winter 2017) Organic Chemistry I Course website: Departmental Office: Room SA 229, Tel: , uginfo@chem.ucalgary.ca 2. Course Description: An introduction to Organic Chemistry from a mechanistic perspective. Structure, bonding, and function, e.g. physical properties and reactivity. Stereochemistry, kinetics and thermodynamics, spectroscopy (nuclear magnetic resonance, infrared, ultra-violet/visible, and mass spectrometric techniques). Substitution and elimination reactions of saturated functional groups - the chemistry of alkanes, alkyl halides, alcohols and their derivatives. Laboratory: Practical techniques. 3. Recommended/ Required Textbook(s): No textbook is required for this course. Students can access the etext available free of charge through the course website ( Links to the etext and other open access resources are provided in the Course Guide document on D2L. 4. Course Learning Outcomes, Topics Covered, and Suggested Readings: Course Learning Outcomes: By the end of this course, students will be expected to: Recognize and employ the conventions of naming, structure drawing, and curved arrow pushing to communicate about organic compounds. Draw reaction mechanisms with appropriate curved arrows to account for how bonds are made and broken in organic reactions Analyze the structural features of starting materials, reaction intermediates, and products to predict or rationalize their physical properties or reaction behaviour. Identify and interpret spectral data to deduce the structure of simple organic molecules. Perform laboratory experiments using techniques that are safe and appropriate for handling and manipulating organic compounds. Propose a short (ca. 1-4 step), feasible synthesis for the formation of a specific organic product using a limited number of possible reaction types: acid/base, radical substitution, nucleophilic substitution, or elimination reactions. Course Content Topics are listed below by keywords, with a list of corresponding chapters from the course website etext. Links to the course website etext (and any other relevant sites) are provided in the Course Guide on D2L. Course Content Topics Fundamentals of Structure and Bonding & the Language of Organic Chemistry Bonding: ionic, covalent, polar covalent bonds, dipoles, etc. Lewis structures of organic molecules Language of organic chemistry (types of arrows, types of diagrams e.g. wedge-hash, Newman, Fischer) VSEPR (shapes of molecules) Chapter in etext (not all sections will be covered) Chapters 1-4, 7

2 Course Content Topics (continued) Introduction to MO theory (orbitals in molecules = where the electrons are) Hybridisation of simple molecules: hydrocarbons, expand to functional groups Formal charge (review, examples of common organic situations) Oxidation state (review, examples of common organic situations) Using curly arrows (rules for drawing/checking/applications) Resonance (definition, reasoning for use, implications on structure/reactivity) pka trends (organic acids and bases, related to structure, factors affecting each, introducing enolates) Bond properties (energies, lengths) Hydrocarbons: types alkanes, alkenes, alkynes, arenes; saturated, unsaturated, IHD Isomers (drawing, constitutional, conformational, configurational, geometric, optical, enantiomers, diastereomers) Intermolecular forces and physical properties (e.g. mp, bp, solubility) Thermodynamic stability: heats of combustion, heats of formation, using Hess's Law Conformational analysis: terminology Conformational analysis of alkanes and cycloalkanes Conformational analysis of substituted cycloalkanes Nomenclature of organic compounds (including stereoisomers e.g. E/Z and R/S terminology) Spectroscopy and related techniques Elemental analysis Infrared spectroscopy: principles, Hookes law model, vibrational modes, polar bonds, characteristic functional group stretches Mass spectrometry: principles, molecular ion, simple fragments, isotope patterns for Cl and Br 1 H NMR spectroscopy: principles, types of H, chemical shift, integration, simple coupling patterns, complex coupling in alkenes and benzenes 13 C NMR spectroscopy: broad band decoupled, compare and contrast with 1 H NMR spectroscopy. Using spectroscopic data to deduce structure Reactions Radical substitution reactions of alkanes to give alkyl halides Radicals (stability factors and trends) n.b. allylic and benzylic radical substitutions Chapter in etext (not all sections will be covered) For nomenclature: Can refer to Chapter 2-6, 9, 11, for general information on naming and reactivity of each functional group (Chapter names match the functional group names, e.g. Chapter 4 Alcohols and alkyl halides ) Chapter 13 Chapter 4-5, 8-9, 15 Nucleophilic substitution reactions of alkyl halides and alcohols (and related systems e.g. thiols, ethers, amines) SN1 mechanism (kinetics, key factors affecting SN1, stereochemistry) Carbocations (stability factors and trends) SN2 mechanism (kinetics, key factors affecting SN2, stereochemistry) Nucleophilicity (factors and trends) Leaving groups (factors and trends) Reactions of alkyl halides with common nucleophiles (including acetylides, enolates, etc.) Reactions of alcohols with HX, PX3, SOCl2 etc. Preparations and reactions of tosylates (as a good leaving group) Ether synthesis (using alcohols or phenols) Elimination reactions of alkyl halides (dehydrohalgenation) and alcohols (dehydration) to give alkenes Alkenes: stability trends based on thermodynamic data (e.g. heats of hydrogenation) related to structure (degree of substitution, E or Z) Zaitsevs rule E1 mechanism Carbocation rearrangements (via 1,2-hydride and 1,2-alkyl shifts) E2 mechanism E2 stereochemistry implications in cyclic systems E1cB mechanism Alkynes from elimination reactions Basicity vs. nucleophilicity Substitution vs. eliminations (factors that influence the major pathway) Application of reactions to the synthesis of organic molecules

3 4. Laboratory Experiments: (10 weeks, 3 hours/ week) 1. Solubility of Organic Compounds 2. Melting point and Boiling point determination 3. Molecular Models (structure and bonding) 4a and b. (2 week experiment) Synthesis of Analgesics (i) acetominophen and (ii) aspirin 5. Reactivity of Hydrocarbons 6. Spectroscopy 7. Isolation of a Natural Product: Caffeine 8. Chromatography 9. Reactivity in Substitution Reactions Department Approval Date

4 SCHEDULE FOR CHEM 351 (WINTER 2018) DATES CLASS TOPICS* TUTORIAL EXPERIMENT Week 1 Jan Fundamentals of Structure and Bonding 2. Language of Organic Chemistry Introduction to Individual and Team components No labs this week Week 2 Jan Week 3 Jan & 2, as well as 3. Acids and Bases Start of Team activities and Team Q-of-the-week Responses 1, 2, & 3 Individual Timed Assignment 1: Nomenclature 1 Check-in 1. Solubility of Organic Compounds 2. Melting Point and Boiling Point Week 4 Jan 29- Feb 2 1, 2, & 3, as well as 4. Energy Diagrams as Problem Solving Tools, Team activities & Q-of-the- 3. Molecular Models 5. Radical Halogenation Reactions Week 5 Feb 5-9 1, 2, 3, 4 & 5, as well as midterm prep/planning/review Individual Timed Assignment 2: Nomenclature 2 4 a. Synthesis of Analgesics Week 6 Feb , 2, 3 & 5 Team activities & Q-of-the- READING WEEK FEBRUARY b. Synthesis of Analgesics Week 7 Feb 26-Mar 2 1 & 2, as well as 6. Structure Determination using Spectroscopic Analyses Midterm** on Wednesday, February 28, 7-9pm NO tutorials or laboratory sessions this week Week 8 Mar 5-9 1, 2 & 6 Team activities & Q-of-the- 5. Spectroscopy Week 9 Mar , as well as 7. Nucleophilic Substitution Reactions and Elimination Reactions Individual Timed Assignment 3: Spectroscopy 6. Hydrocarbons Week 10 Mar Team activities & Q-of-the- 7. Isolation of a Natural Product: Caffeine Week 11 7 no tutorials on Friday, 8. Chromatography Mar no class on Friday, March 30 (Good Friday) March 30 (Good Friday) Week 12 Apr 2-6 7, as well as 8. Conformational Analyses Team activities & Q-of-the- 9. Reactivity in Substitution Reactions Week 13 Apr & 8, as well as final exam prep/planning/review Wrap-up of Team activities & Q-of-the- (Exams begin (final includes 1-8, course is cumulative) April 16) *For detailed descriptions of Class Topics, see Course Guide on D2L Check-out **Midterm will examine students on all content covered up to February 28 th. This includes all lecture, lab, and tutorial content, as ALL course components contain examinable material.

5 Organic Chemistry I CHEM 351 Winter 2018 Instructor, Course and Lab Coordinator: Dr. Wendy Benoit EEEL 235A wlbenoit@ucalgary.ca Course Overview: Office hours and schedule posted on D2L during first week of classes. If you aren t able to make it to office hours, please contact me by to setup an appointment. CHEM 351 provides a chance to see the foundation of organic chemistry, through consideration of structural features and how these link to a compound s properties and reactivity in organic reactions. In many ways, the course may start out feeling very similar to the ideas introduced in first-year chemistry especially in the first few weeks of classes but remember that the familiar pieces are stairsteps toward seeing chemistry through an organic chemistry lens. You will establish a tool kit of nomenclature, structure drawing, arrow pushing, vocabulary, and interpretation of data that you will need to use in assessing reactions and proposing syntheses by the end of the course. Responsibilities and Expectations: My philosophy of teaching is built around a mind-set of growth, where learning is fuelled through cycles of practice and feedback. As your course instructor, I aim to facilitate learning of organic chemistry that can scaffold onto your past experiences and awareness of chemistry. I will frequently pose questions in class to establish clarity on your understanding of a topic before we have discussed it thoroughly; by knowing your initial thoughts, we can move forward and discuss details in a way that is responsive and connected to your past knowledge. There will also be chances to add details onto past concepts or refine your way of thinking to help you build a robust set of tools for solving organic chemistry problems. There will be some rote details to learn along the way, to complement and enhance the tools and approaches needed, but the main goal is to build a foundation of understanding of the features and behaviour of organic compounds and how they react. Coursework components of the course (including both individual and team components) are meant to be opportunities for practice and feedback. Coursework should be viewed as lower-stakes assessment tasks where you ll struggle, make mistakes, seek feedback, and formulate questions to fuel your learning--as you prepare for higher-stakes assessments on midterm and final exams. To support learning in this course, you will have an instructional team (instructors and TAs) that you can consult with in class, lab, and tutorial. In this course, we will also have a team of Peer Mentors who will attend some classes and tutorials; Peer Mentors are students who have taken this course before and have come back to help you do well. This is a cumulative course, and content bridges across all course components (class, tutorial, and lab). To help link the learning experiences in class and in tutorial, much of our work in these spaces will be structured around Collaborative Learning Teams. Students will be assigned a team in the first week of classes and will work with this team throughout the semester; more details on Collaborative Learning Teams are provided in the next section, after listing expectations of instructor and students. All learning environments in this course are places for mutual respect. I will do what I can to establish and maintain an environment of mutual respect, and I expect the same from you.

6 My expectations of you: treat other students, peer mentors, TAs, and instructors with respect arrive prepared and on time to class, lab, and tutorial minimize distraction/disruption for others around you participate actively listen actively be considerate, open, and encouraging of the contributions of others let me know if you are dealing with issues that affect your ability to perform at your best in this class What you can expect from me: treat all students, peer mentors, and instructional team members with respect start and end class on time be available outside class time (e.g. office hours, appointments) to discuss course content or course concerns prepare relevant course materials and post these on D2L in a timely manner reply to s as soon as possible (will aim to reply within 24 hours, not including weekends) Collaborative Learning Teams: In this class, we will use a team framework to support your learning and connect the lecture and tutorial components of the course. The collaborative learning teams will work together throughout the term on assignments and activities, and this work will contribute 10% to your overall course grade (Coursework Team). Here are the details of how collaborative learning teams will work: 1. Teams will be formed in the first week of classes. I will be using ITP Metrics as a tool to aid team formation and divide the class into teams, based on your tutorial section, previous courses taken, your major/year, work experience, and other factors that will help us form successful teams. I will aim to form diverse teams of 6 people, as diverse teams of this size (5-7 people) have been shown to function best and produce good outcomes. 2. I will put measures in place for a Team Contract and Peer Evaluation to provide individual accountability to the team. A Peer Evaluation Score will be calculated for each student, to be used as a multiplier on the Coursework-Team component of each person s grade. 3. You need to be present with your team, in class or in tutorial, to earn a score on the team activity. When calculating scores at the end of semester, each student will be allotted two absences that won t count toward their score (so, only 2 times during the semester could a student who was absent earn their team s score on the class or tutorial activity). Any other absences will require documentation as per the criteria in the University Calendar for Missed Term Work (Section 3.6 and E.3). 4. If you re having issues in your team, please talk with me as soon as possible. Small problems can become large problems if not addressed early on. I m happy to facilitate a discussion with your team to help resolve issues.

7 Tutorial Work: Most weeks will involve working in teams during tutorial sessions. These teams are the same ones you ll be working with during class time; tutorials can be viewed as an extension of the learning activities and discussions we have during lecture time. During weeks 3, 5, and 9, the tutorial sessions will be used for Individual Timed Assignments (see schedule and Course Guide for more details), run under exam-like conditions; these are the only weeks of the term where tutorial work will be completed individually. Laboratory Work Laboratory work will be completed individually and will not be performed with your class/tutorial Collaborative Learning Team. Most experiments (aside from Molecular Models and Spectroscopy Experiments) will involve wet experiments where you will take notes in a self-duplicating laboratory notebook during the lab. A duplicate of notes taken during the experiment is to be handed in to your TA at the end of the lab session. Experimental write-ups will follow the instructions laid out in the online lab manual; many of these require print-out and hard-copy completion of a template (may be due at the end of the lab period or at the start of the next lab session, depending on the experiment follow submission deadlines laid out in lab manual). You must earn a passing lab grade (i.e. 50% or greater) to pass the course. Midterm and Final Exams Midterm and Final Examinations will be cumulative, and the format will be a mixture of multiple choice and written responses. At least one past examination will be provided on D2L in advance of the examination, to aid with study preparations. The examination format will be different than the format of exams on the CHEM 351 website archive; however, even though the format is different, the content being examined is the same and thus the archive s questions can be used as a study tool if desired. There are no deferred midterms in this class. See Course Outline for more details of exam regulations.