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1 Chemistry 282 Syllabus 2016 Course instructor: Dr. J. Carran, Office: CHE511 e-mail: [email protected] Office hours TBA (see course news forum first week of term) Lab coordinator: Dr Jason Vlahakis, Office: CHE215 Lab Manuals: CHEM 282 Lab Manuals (with Basic Laboratory Chemistry” CD) will be available at the Chemistry Stores, Chernoff Hall (CHE109). Labs: Labs start on the first week of classes All CHEM282 labs are in room CHE118 on the ground floor of Chernoff Hall. Tutorials/help-desk: There are no tutorials for chem282, instead we will do some problem sessions in class. In addition to the instructors’ office hours, a teaching assistant at the help-desk will be happy to help you with any question relevant to this course. The help-desk schedule (which will be active after a few weeks when the first sessions begin) may be found at: http://www.chem.queensu.ca/UG/Helpdesk.asp Joshua Clark is the teaching assistant assigned to this course, but feel free to approach other teaching assistants at the help desk when they are available. Text: Organic Chemistry, 11th Edition, G. Solomons and C. Fryhle with Study Guide and Solutions Manual. Exams: NOTE: Midterm #2 is on March 15th from 7.00-9.00pm DO NOT SCHEDULE ANYTHING FOR THIS PERIOD. If you cannot attend this exam at this time your final mark may be reweighted. Grading as below: Online Assignments (WileyPlus): Midterm Examinations x2: Final Examination: Laboratory Grade: 5% 10% (multiple choice, week 4 in class) and 25% (multiple choice/short answer, week 10) 40% 20% Note that you must pass BOTH the lecture (sum of midterm, final exams) and the laboratory components to pass the course. If you do not pass BOTH the lecture (midterms + final exam) and the laboratory components, you will fail CHEM282 (i.e. you will be given an F and 47% or your average mark, whichever is lower, as a numerical grade). Students who do not attend all lab sessions and do not submit all lab reports will be assigned a grade of incomplete (IN ) and be required to attend and pass the missed lab(s) the following year before the IN is cleared from their transcript. Online assignments: Please make sure your student number is used when you input your information when registering for WileyPlus (this is only for new registrants, those students who were in WileyPlus can use their old login information tom access the online assignments). Please note that as I give plenty of time to complete assignments there will be ZERO extensions given. DO NOT MISS DUE DATES/TIMES AND MAKE SURE YOU CHECK THEM CAREFULLY. Lecture Outline It is recommended that students familiarize themselves with the required reading before attending the corresponding lectures. Note lecture sequence is approximate and may differ to what is noted below. Conjugated Systems Required Reading – Solomons - Chapter 13 Lecture 1 - Conjugated Systems – Lecture 2 - Conjugated Systems - The Diels Alder Reaction - Part 1. Lecture 3 - Conjugated Systems - The Diels Alder Reaction - Part 2. Aromatic Molecules - 1 Required Reading – Solomons - Chapter 14/15 Lecture 4 - Aromatic Molecules - Aromaticity, Hückel Theory. Lecture 5- Aromatic Molecules - Resonance and Spectroscopy. Lecture 6- Aromatic Molecules - Reactivity - Electrophilic Aromatic Substitution (EAS), Friedel-Crafts Acylation and Alkylation. Aromatic Molecules - 2 Required Reading – Solomons - Chapter 14/15 Lecture 7 - Aromatic Molecules - Reactivity - Directing Groups and Selectivity. Lecture 8 - Aromatic Molecules - Reactivity Lecture 9 - Aromatic Molecules - Reactivity - Synthetic Strategies - Protecting Groups, Functional Group Interconversion (FGI). Alcohols and Ethers Required Reading – Solomons - Chapter 11 (NOTE: some of this is a recap from 281 and will be covered quickly) Lecture 10 - Alcohols and Ethers - Nomenclature, Structure, Reactivity. Lecture 11 - Alcohols and Ethers - Synthesis and Protection. Lecture 12 - Alcohols and Ethers - Synthesis via Epoxidation. Alcohols and the Carbonyl Group Required Reading – Solomons - Chapter 12 Lecture 13 - Alcohols and the Carbonyl Group - Introduction to the Carbonyl Group. Lecture 14 - Alcohols and the Carbonyl Group - Addition to the Carbonyl Group (Grignard Reagents, Organolithiums). Lecture 15 - Alcohols and the Carbonyl Group - Reduction, Oxidation and Protection. Organic Radicals Required Reading – Solomons - Chapter 10 Lecture 16 - Radicals - Stability, Structure and Generation. Lecture 17 - Radicals - Mechanism and Selectivity. Lecture 18 - Radicals - Application, Examples, polymerisation Reading week Lecture Outline After Reading Week Reading assignments are the chapters indicated (check lecture notes for topics not covered). Chapter 16 Aldehydes and ketones, synthesis of and reactions of, including acetal formation, amine additions, HCN addition, Wittig reaction. Chapter 17 Carboxylic acids and their derivatives. Nomenclature, physical properties, synthesis and reactions. Nucleophilic addition- elimination reaction at the acyl carbon. Step – Growth Polymers. Chapter 18.1-18.7 Aldehydes and ketones, reactions of α-C-H. Keto and enol tautomers. Reactions via enols and enolate ions including racemization, halogenation, and aldol reaction. Malonic and acetoacetic ester synthesis. Lithium enolates. Chapter 19.1 –19.6 Dicarbonyls, synthesis and reactions, Claisen condensation, crossed aldol condensation , cyclization via aldol condensation. Chapter 20.1-20.5 Amines, properties and synthesis. Chapter 22 Carbohydrates. Monosaccharides, properties and reactions. Disaccharides and polysaccharides. Chapter 23 Lipids and fats, steroids. Biosynthesis of cholesterol. Cholesterol and heart disease (time permitting, this lecture section is often truncated) Chapter 24 Amino acids and peptides. Friendly Advice: 1) All of you have taken CHEM281, which is a required pre-requisite for CHEM282. Do not forget the information in that course because you will need it to understand the material being given in CHEM282. In CHEM282 the great bulk of the material will focus on functional group transformations. We make the assumption that you are familiar with the material taught in CHEM281 and will not review this unless it is necessary to introduce an additional concept. There will be a lot of new material covered in the course: the majority of this will be easier if you try to understand the chemical principles behind the topic. Homework will be assigned, and will be graded (WileyPlus). Do not fall behind and do not miss lectures. One of the surest ways to get wiped out in this course is to fall too far behind, thinking that you can catch up. Students who are most successful at this course are those who keep up with the material and understand it as it is presented. 2) The lecture notes take precedent on the textbook material. You are responsible for the material covered in class which may not be covered in the textbook, unless specified (e.g. special topics are NOT included in the exam material, listen in class for important announcements). STANDARD QUOTATION REGARDING ACADEMIC BEHAVIOUR All students must adhere to the Queen’s University policy on plagiarism and academic honesty (see appropriate sections of Academic Regulations in Arts and Science Calendar). Academic integrity is constituted by the five core fundamental values of honesty, trust, fairness, respect and responsibility (see www.academicintegrity.org). These values are central to the building, nurturing and sustaining of an academic community in which all members of the community will thrive. Adherence to the values expressed through academic integrity forms a foundation for the "freedom of inquiry and exchange of ideas" essential to the intellectual life of the University (see the Senate Report on Principles and Priorities) Students are responsible for familiarizing themselves with the regulations concerning academic integrity and for ensuring that their assignments conform to the principles of academic integrity. Information on academic integrity is available in the Arts and Science Calendar (Error! Not a valid link.), on the Arts and Science website (see http://www.queensu.ca/calendars/artsci/pg4.html), and from the instructor of this course. Departures from academic integrity include plagiarism, use of unauthorized materials, facilitation, forgery and falsification, and are antithetical to the development of an academic community at Queen's. Given the seriousness of these matters, actions which contravene the regulation on academic integrity carry sanctions that can range from a warning or the loss of grades on an assignment to the failure of a course to a requirement to withdraw from the university. assignment to the failure of a course to a requirement to withdraw from the university.