Dalhousie University Faculty of Agriculture CHMA2000 Organic Chemistry I Course Outline Fall 2017

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1 Professor: Dr. Jeff Hoyle Office: Cox Institute Lab Instructor: Ms. Margie Tate Office: Cox Institute Lab Instructor: Mr. Fred Fergus Office: Cox Institute Class Time: Classes will be held on Wednesday and Friday from 8.30am until 9.55am in Cox Institute room 024. Labs will be held in Cox 240/245. Course Description: This course provides an introduction to the structure and reactions of organic compounds. The course is approached from a mechanistic point of view and has particular emphasis on appropriate spectroscopy (IR and MS). The topics covered in this course include chemical bonding, isomerism, acid base properties and the isolation and purification of organic compounds. The classes of organic compounds covered will include alkanes, alkenes, alkynes, simple aromatics, organohalides, alcohols, and related compounds. Laboratory work will include introductory techniques of organic chemistry and both HPLC and gas chromatography. Learning Outcomes: Apply the IUPAC rules of organic nomenclature, including the ability to name selective organic compounds and draw correct structures from names. Understand and apply key terms in organic chemistry. Demonstrate and perform basic organic laboratory techniques; understand the background to each of these techniques Illustrate chemical structures and relate them to physical and chemical properties of organic compounds Draw and interpret proper Lewis structures, including comprehension of contributing resonance structures Interpret fundamental laboratory results related to organic chemistry Recognize the structures of lipids, proteins and carbohydrates in the context of the rest of the course 1

2 Correlate molecular structure and spectroscopic behavior for simple organic compounds (infra-red and mass spectra) Draw, distinguish and name isomers of organic compounds - R/S, E/Z and cis/trans Predict and justify the mechanisms and outcomes of acid/base, addition, substitution and elimination reactionss, propose and draw reasonable 'arrowpushing' mechanisms Propose reaction sequences and conditions for the preparation of organic compounds Create graphs/figures to interpret, predict and explain kinetic phenomenon relating to reactions Textbooks: Any edition of Organic Chemistry by L.G. Wade. The newest edition is the 9 th. Below are what 8 th and 9 th editions look like.this book is available for purchase in the bookstore or at other reputable outlets. I VERY STRONGLY suggest that you have access to this book. Course Requirements and Grading: Grading: Classroom Portion of course (70%) Test I 5 % (15 September) Test II 12 % (18 October) Test III 19 % (probably 15 November) Exam 30 % (scheduled by Registrar) Quizzes 4% 2

3 Grading: Lab Portion of course (30%) (see Friday class for complete details) Type of Report/Test Number of Reports Value/Report (%) Total Value (%) paper Formal 3 2/3/4 9 Written lab test Practical lab test Tests/Exam: The tests and examination are cumulative. This means that each one may include all course material covered up to that date. However, tests will place more emphasis on material covered since the previous test. Students may start tests 10 minutes early if they wish, but should finish promptly by the end of class. There are no makeup tests. The following test, or the exam, accumulates the marks of the missed test. Quizzes: Quizzes will be announced a few days ahead of time. If you miss a quiz without an excuse acceptable to Dr. Hoyle, then you will be assigned a mark of 0 for that quiz. Laboratories: Full lab details, including safety, will be presented in class on Friday September 8. Labs are a mandatory portion of CHMA2000, with the exception of those students who have previously completed the lab portion of the course.* Students will be required to attend one 3-hour lab per week. Due to personnel constraints, students will NOT be able to make up labs at non-scheduled times. If students miss a lab without a legitimate excuse, then they may be assigned 0 for that lab. Late lab reports will incur a penalty of 15% per day, or part thereof. Students are expected to wear a full length lab coat and eye protection at all times. Contact lenses are NOT permitted in the lab, nor are sandals. Long hair is to be tied back. There is no printed lab manual, everything is available on the internet. * Students who have previously taken CHMA2000 and passed the lab component of the course are eligible for an exemption of the lab report portion of this course. Their score from previous lab reports will be used to determine their lab report grade. These students must still complete the written and practical lab test. Eligible students must see Ms. Tate to advise whether they will redo lab experiments or accept their exemption on the above conditions. Once decided this decision may not be reversed. 3

4 Final course grade: A final letter grade will be assigned based on the following scale: Course Schedule: Percentage Grade A A A B B B C C C D F The course is broken down into units (1-11) as listed below. This is not a sequential list and some material will be self-study. We start with Unit 1 J (1) Introduction (Chapters 1 and 2) - What is organic chemistry - Organic Chemist s Periodic Table - Electron configuration and atomic structure - Chemical bonds - Electronegativity, polarity, and dipole moments - Resonance - Acids and bases, nucleophiles and electrophiles - Reactive chemical species in organic chemistry - Functional groups (2) Alkanes (Chapter 3) we spend a long time on this unit - Formulae - Nomenclature this is the basis for naming all organic compounds! - Structures - Physical properties - Uses and sources - Chemical reactions of alkanes - Conformations this is the basis for all organic compounds!! 4

5 (3) Alkenes (Chapters 7 and 8) - Common alkenes - Structures - Degree of unsaturation (double bond equivalent) - Nomenclature - E/Z isomers - Cycloalkenes - Preparation of alkenes - Chemical reactions of alkenes (4) Alkynes (Chapter 9) - Nomenclature and structure - Similarities to alkenes - Preparation and reactions of alkynes (5) Alkyl Halides (Chapter 6) - Nomenclature - Structure - Common compounds and uses - Physical properties - Preparation of alkyl halides - Reactions of alkyl halides (6) Alcohols (Chapters 10 and 11) - Naming - Inorganic acid esters - Synthesis - Reactions - Brief comments on amines, ethers, thiols, sulfoxides, and sulfones (7) Infrared and/or Mass Spectrophotometry (Chapter 12 in brief, time permitting) (8) Aromatic Compounds (Chapter 16 and 17 in brief) - Naming - Structure - Common ring systems - A reaction: electrophilic aromatic substitution (9) Carboxylic Acids and Derivatives (Chapters 20/21 in brief) - Naming - Structure - Preparation and hydrolysis 5

6 (10) Biological Compounds (Chapters in brief) Carbohydrates and monosaccharides. Proteins and amino acids. Lipids, fatty acids, and glycerol (11) Isolation, identification, and purification of compounds (VERY detailed mostly in lab) Accommodations and Academic Support: If you are having difficulty with course content or have challenges meeting any of the deadlines, please contact the professor for this course as soon as possible to discuss your options. Any student who may require academic accommodations is encouraged to meet with Bev Zinck, Coordinator of Academic Accommodations in Student Services, Dairy Building. She can also be reached at (902) or You can learn more about academic accommodations at: Use of plagiarism detection software: All assignments may be submitted to Dalhousie s current plagiarism detection software, a program that compares documents to online sources. If you do not wish to have your assignments submitted to this software, you must notify me of that within the first week of class, and we will arrange other methods to verify that the work is yours, such as submitting all drafts and resource notes in addition to the assignment. Academic Integrity: It is understood that students will work together doing lab exercises, so it makes sense that students work together on their laboratory reports. HOWEVER it is very important to note that this collaboration should ONLY be at the discussion of procedure and results stage. STUDENTS MUST WRITE THEIR REPORTS INDEPENDENTLY. If you are not sure what this means, please seek clarifications from Ms. Tate prior to the first lab report deadline. At Dalhousie University, we are guided in all of our work by the values of academic integrity: honesty, trust, fairness, responsibility and respect (The Center for Academic Integrity, Duke University, 1999). As a student, you are required to demonstrate these values in all of the work you do. The University provides policies and procedures that every member of the university community is required to follow to ensure academic integrity. We must all work together to prevent academic dishonesty because it is unfair to honest students. The following are some ways that you can achieve academic integrity; some may not be applicable in all circumstances. make sure you understand Dalhousie s policies on academic integrity (see 6

7 do not cheat in examinations or write an exam or test for someone else do not falsify data or lab results be sure not to plagiarize, intentionally or unintentionally, for example o clearly indicate the sources used in your written or oral work. This includes computer codes/ programs, artistic or architectural works, scientific projects, performances, web page designs, graphical representations, diagrams, videos, and images o do not use the work of another from the Internet or any other source and submit it as your own o when you use the ideas of other people (paraphrasing), make sure to acknowledge the source do not submit work that has been completed through collaboration or previously submitted for another assignment without permission from your instructor (These examples should be considered only as a guide and not an exhaustive list.) If you are ever unsure about any aspect of your academic work, you should talk with your professor or go to one of the following resources: Academic Integrity website (see ) - Links to policies, definitions, online tutorials, tips on citing and paraphrasing Writing Centre (see - Assistance with learning to write academic documents, reviewing papers for discipline-specific writing standards, organization, argument, transitions, writing styles and citations Dalhousie Libraries (see - Workshops, online tutorials, citation guides, Assignment Calculator, RefWorks What will happen if an allegation of an academic offence is made against you? As your instructor, I am required to report every suspected offence. The full process is outlined in the Faculty Discipline Flow Chart (see Review of Grades: Students who have questions about final grades that are assigned are encouraged to discuss them with the course instructor. In addition, students should consult the chair of the department or an academic advisor. If their concerns cannot be resolved, students may also use the formal process that follows for the re-assessment of final grades, as set forth in the Dalhousie University Calendar, except when such grades are the result of an academic discipline penalty. Form revised August 2016 Associate VP Academic Office 7