YOU MUST PURCHASE WILEYPLUS FOR THIS COURSE

1. YOU MUST PURCHASE WILEYPLUS FOR THIS COURSE see SDSMT Bookstore

2. Turn off cell phones before each class. • No textmessagingin class. No headphones. If you wish to use a laptop in this class for purposes of note taking, that’s great, but if you are caught playing games or browsing web sites or other non-organic activities you will be asked to leave, or dropped from the course. During classtime screens must be locked in the down position if you use your tablet during class. • No talking during class is tolerated. You will be dropped from the course. • Tablets or laptops will be used for the class. It is the student’s responsibility to ensure working technology at all times. The instructor will not provide any tech support nor give exceptions for any computer problems.

3. Organic Chemistry I Chem 326 3 Credits South Dakota School of Mines and Technology Fall 2011 MWF 10:00-10:50 Dr. David A. Boyles Room 319 Chemistry Bldg

4. Prerequisites: Chem 112 Chem 112L Chem 114 YOU WILL BE REQUIRED TO DRAW ON THIS MATERIAL! • GEN CHEM SUBJECT MATTER YOU MUST KNOW IN ADVANCE OF THIS CLASS: • Periodic Table: Trends, common elements, spelling and abbreviations of elements • Electron configurations of H, B, Al, C, N, O, S, X • Lewis dot configurations of elements, compounds, ions with geometries by VSEPR • Nomenclature of inorganic compounds • Defined: Chemical structure versus chemical formula • Chemical structure and chemical formulae of six strong acids • Chemical reactions of acids and bases when dissolved in water

5. Organic Chemistry = the chemistry of carbon compounds Chemistry = study at the molecular level of the classification, synthesis, reactions, nomenclature properties • At least 7 million organic compared with 1 million inorganic compounds.

6. Fuels: gasoline, kerosene, jet fuel Plastics and elastomers: polyethylene polypropylene polystyrene poly(vinyl chloride) polycarbonates poly(ethylene terephthalates) polyurethanes rubbers Fibers: wool, silk, leather rayon nylon acrylates, PET Dyes: Pharmaceuticals: antibacterials, antivirals, antifungals, anticancer, antiparasitic, antifertility, antiinflammatory, antidepressants, anticonvulsants… Agriculture: insecticides, fungicides, herbicides Detergents: soaps, surfactants Food: oils, fats, proteins, carbohydrates Perfumes and Flavors • The foundation for further study in • Chemistry • Biochemistry, • Polymer chemistry, Pharmaceutical chemistry • Chemical Engineering Industrial chemistry • Medicine (Paracelsus, 1493- 1591)

7. Organic chemistry is pervasive in the global economy and is a major source of GDP of developed nations

9. Chemistry is an experimental science (Robert Boyle, The Sceptical Chemist, 1661) Unlike philosophy which works with ideas alone to try to understand the world, what is under discussion in science is what actually is known to occur in the physical world We are not concerned with what doesn’t happen Organic chemistry is not just a “paper exercise” but is a formal system of knowledge grounded in what is experimentally known to occur This two semester course concerns WHAT happens; in other words, this course is descriptive of the world of carbon chemistry, it DESCRIBES the world of carbon compounds How do we describe such a world?

10. 1. ORGANIC CHEMISTRY IS HIGHLY SYSTEMATIZED: A FORMAL SYSTEM OF KNOWLEDGE = EVERYTHING IS ORGANIZED BY RULES

11. 2. To learn organic chemistry is to learn not only what can and does happen in the world of carbon compounds, but to learn how to represent and predict what happens Organic chemistry uses symbolic representations of that world you must learn: A representation is not the reality A map is not the territory Representations must be learned and maps must be created; reality does not come with labels

12. LOW-GRADE BEHAVIOR = non-thinking behavior….

13. ANY DOG CAN CHASE A FRISBEE…

14. LOOK PASSIVELY GAWK ▸ verb:  look with amazement; look stupidly

16. LISTEN PASSIVELY also known as “zoning out” for a reason…

17. ….which IN CLASSROOMS is known as…

18. ARE TALKED TO = STUDENT PASSIVITY

19. “IN ONE EAR AND OUT THE OTHER”

20. THE TROUBLE WITH LECTURE…. THE MORE I LECTURE…THE MORE YOU WATCH and LISTEN… THE MORE YOU ARE PASSIVE, THE MORE YOU FOOL YOURSELF INTO THINKING YOU UNDERSTAND…SO…. THE LESS YOU STUDY… THE LESS YOU COME TO CLASS PREPARED…. THE LESS YOU LEARN AND REMEMBER…. THE LESS COMPETITIVE YOU ARE WITH STUDENTS ELSEWHERE….INCLUDING HERE THE LESS EDUCATION YOU GET FOR YOUR MONEY

21. Make no mistake! ORGANIC CHEMISTRY IS AN…

22. QUESTION: HOW DO YOU EAT AN ENTIRE ELEPHANT? ANSWER… ONE BITE AT A TIME Inch by inch…anything’s a cinch!

23. TO COUNTERACT THE TENDENCY TO STUPID, YOU MUST ENGAGE WITH THE TEXT OUTSIDE EVERY CLASS PERIOD = “HOMEWORK” DISCOVER YOUR WEAKNESSES AND THE MENTAL HURDLES TO LEARNING ORGANIC EARLY IN THE GAME The sooner you begin to make your first 10,000 mistakes, The sooner you may begin to correct them. --Nicolaides Learning formal knowledge systems takes work, intellectual work. Intellectual work is the counterpart of manual labor.

24. STUDY—A NOBLE PATH TO WISDOM L. studium "study, application," originally "eagerness," from studere "to be diligent" Diligence = Industrious "characterized by energy, effort, attention" (1552) “Do, or do not. THERE IS NO ‘TRY.’ --Jedi Master Yoda

25. “The academic norm is that each class period involves one hour of work in class and two hours outside of class for every hour in class” ---Regent Policy Manual YOUR MILEAGE MAY VARY… THE SOONER YOU MAKE YOUR FIRST 10,000 MISTAKES…. THE SOONER YOU MAY BEGIN TO CORRECT THEM…

26. Types of thinking involved in this course • 1. Verbal • multisyllabic terminology • highly standardized terminology • 2. Logical • chemical structures have names based on molecular features • 3. Memory • organic chemistry has its alphabet(s) that MUST be committed to memory • 4. Analogical • a reaction that occurs for one compound will similarly occur for similar compounds—allows us to predict reactions without doing every one of them in the laboratory • LOOK FOR SIMILARITIES AMONG REACTIONS, COMPOUNDS • 5. Symbolic • organic chemistry has unique symbols to describe reality • 6. Abstract • terminology, symbol, reactivity occur together

27. Upper classmen Take responsibility for your own learning This course is structured to promote becoming independent as a learner. Active learning—not passive: work with the text Text in 10th edition with solutions manual Time out of class Two hours undistracted time out of class for each hour in class Read and digest 17 pages each class period Mountain reflected in lake Concept: Knowledge comes in chunks, not bytes Example: “Lewis Acid”—definition, examples, other types of acids Formal knowledge systems do not come to us on our terms I do not give the grade, the requirements of the course knowledge do Organic chemistry is a rule-based system hyphens, commas, spelling: must be done according to the rules or it is wrong Not about you, not about me You are the easiest one for yourself to fool –Richard Feynman

29. RULES OF THE GAME SYLLABUS WRITE DOWN THIS LINK NOW NOWNOW: http://boyles.sdsmt.edu/SyllabiFall2012/Chem326.htm CONTAINS THE ANSWER TO EVERY QUESTION I AM ASKED WHEN I REPLY ‘READ THE SYLLABUS’ EXPECT A QUIZ ON THE SYLLABUS

30. Attendance • Required. Period. • Makeups for school sponsored activities ONLY as per university policy. Period. • No exams or quizzes given other than at scheduled time. Period.

31. IF YOU WANT SOMETHING I EXPECT THAT… YOU REGISTER YOUR REQUEST IN PERSON AT THE APPROPRIATE TIME THIS IS NOT A DISTANCE CLASS, THEREFORE I do not play telephone tag with students I do not answer student email I am not on Facebook, LinkedIN, Twitter or other cutsey venues I ABHOR handheld devices of EVERY sort BE WHERE YOU ARE NOW, NOT SOMEWHERE ELSE YOU AREN’T

32. Kant’s Categorical Imperative "Act only according to that maxim whereby you can, at the same time, will that it should become a universal law.“ Emmanual Kant , Grounding for the Metaphysics of Morals 1785 In other words ask yourself “What if EVERYONE did what I am now doing?” -texted while driving -emailed Dr. Boyles constant updates to your changing schedule -talked out of turn -walked on the wrong side of the hall -went in the left door instead of the right -ignored the speed limit -got up out of their seat during an exam

33. OFFICE HOURS • BY DEFINITION ARE THE HOURS WHEN YOU MAY SEE ME FOR PROLONGED QUESTIONS ONLY • DON’T ANNOY ME AND ASK IF YOU MAY SEE ME DURING MY OFFICE HOURS, OKAY?? THAT’S WHAT THE HOURS ARE FOR! FOR SHORT QUESTIONS ON MATERIAL SEE ME IMMEDIATELY AFTER CLASS BEFORE I GO TO MY OFFICE Jot down questions so you don’t forget them—unless indicated I do not take random questions in a class this large

34. 1.    When to see me: Office hours without appointment; Office hours are MWF 11:00 to 11:50. THE best time to see me is immediately after class while I am yet in class if you have quick questions--don't put them off--there will be new material tomorrow.  I handle quick questions quickly and they usually do not need office time. By appointment made while I am yet in class after class but only if you cannot follow above directions.  For BRIEF questions see me immediately after class while I am yet in  the classroom.  2.    When NOT to see me: • Immediately before class. • When I am obviously in a hurry, or when I am clearly in serious conversation with someone else--wait your turn. • When I am with chemicals or in the laboratory.  3.    When you MUST see me in my office and not in public: Private matters including grades issues, medical issues, personal matters—yours, not mine.

35. NOTE WELL. ETHICS I DO NOT DISCUSS WITH ANY INDIVIDUAL ANY MATTER OF CONCERN TO THE ENTIRE CLASS If your question is in the interest of the entire class, ask before the entire class NO INSIDER SECRETS!! 2. I DO NOT REPEAT WHAT I HAVE ALREADY PUT IN WRITING AND WHAT YOU ARE GIVEN ACCESS TO—SYLLABUS, ASSIGNMENTS, OFFICE HOURS ….to do so fosters learned helplessness on your part 3. I DO NOT ANSWER QUESTIONS BEFORE OR DURING QUIZZES AND EXAMS …..I want to know what YOU know, and what sense you make of the question and the material, even if there is a typo OR ambiguity Everyone has the same information including typos

36. GRADING • There will be • Pre-lecture, daily quizzes: must be taken BEFORE class • Chapter quizzes • Examinations (~2 or 3) • 4. A comprehensive final over the semester will be given 2-3:50 p.m. December 14 Quizzes ~20% Exams ~60% Comprehensive ~20% Approximately in this class: A = 10% 8 students B = 20% 16 students C = 40% 32 students D = 20% 16 students F = 10% 8 students

37. ASSIGNMENTS AT END OF EACH PERIOD: 1.1 TO 1.8 FOR THIS FRIDAY APPROXIMATELY 10-11 CHAPTERS COVERED THIS SEMESTER ~ 550 PAGES/ 35 PERIODS = 17 PAGES/ PERIOD • KEEP IT IN PERSPECTIVE— • WIDE MARGINS • LOTZA PICTURES • YOU HAVE SOLUTIONS TO EVERY PROBLEM-- USE SOLUTIONS MANUAL and WILEYPLUS

38. READING--GUESS WHAT? YOU WON’T UNDERSTAND EVERYTHING YOU READ THE FIRST TIME—PEOPLE OVERESTIMATE THEIR INTELLIGENCE AND ABILITY YOU WILL NOT BE ALONE—Everyone is in the same boat and faces the same assignment and quiz YOUR COMPREHENSION WILL IMPROVE WITH TIME AND EFFORT— AS LONG AS YOU DO NOT PASSIVELY “READ”

39. 3R Method This is intellectual work—to keep your mind active and not going on automatic and passive pilot • 1. READ—do not merely highlight • 2. RECITE—ask yourself to summarize in points what you have read • 3. REVIEW—summarize your study session before leaving it (The mind is a sieve---full of holes stuff leaks out of)

40. 1 THE BASICS: Bonding and Molecular Structure   1 1.1 We Are Stardust2 1.2 Atomic Structure 2 1.3 The Structural Theory of Organic Chemistry 5 1.4 Chemical Bonds: The Octet Rule 7 1.5 How to Write Lewis Structures 9 1.6 Exceptions to the Octet Rule 11 1.7 Formal Charges and How to Calculate Them 13 1.8 Resonance Theory 15 1.9 Quantum Mechanics and Atomic Structure 20 1.10 Atomic Orbitals and Electron Configuration 21 1.11 Molecular Orbitals 23 1.12 The Structure of Methane and Ethane: sp3 Hybridization 25 THE CHEMISTRY OF . . . Calculated Molecular Models: Electron Density Surfaces 29 1.13 The Structure of Ethene (Ethylene): sp2 Hybridization 30 1.14 The Structure of Ethyne (Acetylene): sp Hybridization 34 1.15 A Summary of Important Concepts that Come from Quantum Mechanics 36 1.16 Molecular Geometry: The Valence Shell Electron Pair Repulsion Model 38 1.17 How to Interpret and Write Structural Formulas 41 1.18 Applications of Basic Principles 46

41. REMEMBER…. Winners are simply those …. Who do things losers don’t want to do http://boyles.sdsmt.edu/SyllabiFall2012/Chem326.htm