Mercyhurst College Organic Chemistry I ( Sec.1) Winter Term 2013 Chemistry 240 Dr. J. Williams (ex. 2386, 309 Zurn) Department of Chemistry and Biochemistry http://math.mercyhurst.edu/~jwilliams/ Lecture: MWF 2:40-4:10 PM 313 Zurn Required Material: Organic Chemistry with Biological Applications: John McMurry, Thomson, Brooks/Cole Virtual Textbook of Organic Chemistry http://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/intro1.htm Description: Organic Chemistry I is an introduction to the theories and principles of the chemistry of carbon compounds. The student will develop an understanding of organic chemistry, which will be useful in the studies of chemistry and related fields such as biochemistry, medicine, forensics, engineering and pharmacy. Homework: Homework will be assigned regularly. The homework problems will not be graded nor collected. Selected homework problems will be reviewed in class. Study Time: You should plan to spend about 2 hours studying for each hour of class lecture. Web Site: I have provided a link to an excellent web site filled with practice problems and additional help on Chapter material. In addition your textbook has a website for Organic Chemistry. Since exam questions may mirror website content, I suggest that you spend some quality time at these web sites. Course Objectives: (Time may prevent the coverage of all of these objectives) Upon successful completion of this course the student should be able to: 1. Describe the structure of molecules through the application of chemical bonding theories. 2. Predict properties of organic molecules on the basis of molecular structure. 3. Analyze organic reactions in terms of physical organic principles. 4. Use the IUPAC system of nomenclature and parts of the common naming system. 5. Describe the structure and reactions of alkanes and cycloalkanes. 6. Interpret selected chemical reactions using appropriate mechanisms. 7. Demonstrate an understanding of stereochemistry. 8. Describe the structure and reactions of alkyl halides. 9. Apply general chemical principles to analyze aliphatic substitution and elimination reactions. 10. Describe the structure, synthesis and reactions of alkenes. 11. Describe the structure, synthesis and reactions of alkynes. 12. Descrobe the strucuire, synthesis and reactions of alcohols. 13. Identify unknown structures with the use of infrared spectra and other data. 14. Demonstrate critical thinking skills pertaining to the analysis of organic reactions.
Caveats: Computer Literacy Expectations: Students will need basic word processing and Internet searching skills for the completion of some papers, exercises and projects. Content Outline & Competencies: (Time may prevent the coverage of all of these objectives) I. Molecular Structure and Chemical Bonding Theories A. Draw Lewis electron dot structures for molecules. B. Draw resonance forms for a molecule having delocalized bonding. C. Determine the relative stability of resonance forms using formal charges. D. Apply the VSEPR model to describe molecular geometry and shape. E. Draw a three-dimensional representation of a given molecule. F. Discuss the formation of a covalent bond. G. Identify bonds as covalent or ionic. H. Describe the electronic structure of molecules using valence bond theory. I. Predict the hybridization state of atoms in a molecule. II. Structure and Properties of Organic Molecules A. Predict whether a molecule has a net dipole moment. B. Identify the type(s) of intermolecular forces which operate between molecules. C. Predict general trends in boiling points and solubilities based on intermolecular forces. D. Predict relative acidities and basicities based on structure, bonding and resonance forms of conjugate acid-base pairs. E. Predict the direction of Brönsted-Lowry acid-base reactions. F. Identify Lewis acids and bases. G. Identify by name the following type of compounds (given a condensed structural formula): alkanes, alkenes, alkynes, aromatic hydrocarbons, alkyl halides, alcohols, ethers, aldehydes, ketones, carboxylic acids, esters, amides, amines and phenols. H. Draw condensed structural formulas for the following types of compounds: alkanes, alkenes, alkynes, aromatic hydrocarbons, alkyl halides, alcohols, ethers, aldehydes, ketones, carboxylic acids, esters, amides, amines and phenols. III. Nomenclature A. Given the structure, provide correct IUPAC names for alkanes, cycloalkanes, alkenes, alkynes, dienes and alkyl halides. B. Given the name, draw correct condensed structural formulas for alkanes, cycloalkanes, alkenes, alkynes, dienes and alkyl halides. C. Draw and use common names for all 3- and 4-carbon alkyl groups. IV. Structure and Stereocemistry of Alkanes and Cycloalkanes A. Name and draw structures for alkanes and cycloalkanes by the IUPAC system. B. Identify carbon and hydrogen as being primary, secondary or tertiary. C. Draw all possible isomers given the molecular formula. D. Draw Newman projections for different conformations and predict relative stability. E. Discuss the applicability of Bayer strain theory to the stabilities of cycloalkanes. F. Compare and contrast the terms ring and angle strain. G. Draw structures for both boat and chair cyclohexane. H. Distinguish (by drawing) the difference between axial and equatorial positions in cyclohexane. I. Recognize cis and trans isomers of disubstituted cyclohexanes. J. Predict the stability of substituted cyclohexanes by estimating steric interactions.
K. Draw and explain the radical mechanism for the halogenation of alkanes. L. Explain the relationship of the structure of free radicals to stability. V. The Study of Chemical Reactions. A. Classify organic reactions as addition, elimination, substitution or rearrangement. B. Distinguish between polar and radical mechanisms. C. Identify reagents as electrophiles and nucleophiles. D. Apply thermodynamic concepts to the analysis of organic chemical reactions. E. Calculate the enthalpy change for a reaction from a table of bond energies. F. Relate the equilibrium constant for a chemical reaction to the standard free energy change for that reaction. G. Apply qualitative ideas from transition state theory to the analysis of organic chemical reactions. H. Draw and interpret an energy diagram for a chemical reaction. I. Discuss the meaning of the term activation energy. VI. Stereochemistry A. Recognize the difference between constitutional isomers and stereoisomers. B. Determine if an object or molecule is chiral. C. Apply the RS system of nomenclature to stereoisomers. D. Compare and contrast, using examples if necessary, the following terms: enantiomers, diasteromers and meso compounds. E. Draw Fischer projections of chiral compounds. F. Explain the difference between relative and absolute configurations. G. Predict the theoretical number of stereoisomers. H. Predict the stereochemical outcome of selected reactions. VII. Alkyl Halides: Nucleophilic Substitution and Elmination A. Name and draw structures for alkyl halides by the IUPAC system. B. Show by reaction the preparation of alkyl halides. C. Predict the products of reactions of alkyl halides. D. Discuss the kinetics involved with nucleophilic substitution reactions. E. Classify reactions as SN1, SN2, E1 or E2. F. List a set of ideal conditions for SN1, SN2, E1 or E2 reactions. G. Discuss the factors that can influence the rates of SN1, SN2, E1 or E2 reactions. H. Predict the products of SN1, SN2, E1 or E2 reactions. I. Explain the limitations placed upon elimination reactions that involve the cyclohexane ring. VIII. Alkenes, Alkynes A. Name and draw structures for alkenes and alkynes by the IUPAC system. B. Determine the degrees of unsaturation of an organic compound from its molecular formula. C. Discuss the bonding and electronic structure of alkenes. D. Draw and name cis-trans isomers of alkenes. E. Apply the sequence rules to classify alkenes as E or Z isomers. F. Use heats of hydrogenation to determine the relative stability of alkenes. G. Show by reaction the preparation of alkenes, alkynes and conjugated dienes. H. Predict the products of reactions of alkenes, alkynes and conjugated dienes. I. Discuss the bonding and electronic structure of alkynes. J. Compare and contrast the reactions of alkenes and alkynes. K. Explain why the terminal hydrogen in terminal alkynes is acidic. L. Explain the unusual stability of conjugated dienes.
X. Mechanisms A. Draw and discuss each step of the mechanism of an alkene addition reaction. B. Explain the relationship of carbocation structure to stability. C. Recognize when carbocation rearrangement is likely to occur. D. Apply the Hammond postulate to the analysis of a reaction mechanism. E. Draw and explain the mechanism for a SN1, SN2, E1 or E2 reaction. XI. Spectral Interpretation A. Identify functional groups by their infrared absorptions. B. Correlate the infrared spectrum of a known organic compound to its structure. C. Propose a structure for an unknown consistent with its infrared spectrum and other data such as the molecular formula. XII. Critical Thinking A. Devise a reasonable synthetic pathway for producing a desired compound from a specific starting material. B. Propose a reaction mechanism to explain the outcome of a reaction you have never seen before. C. Determine the structure of an unsaturated compound from its molecular formula and its cleavage and/or hydrogenation products. Methods of Evaluation of Competencies: Evaluation of student mastery of course competencies will be accomplished using the following methods: All exams will be taken in class: Exams 200 pts. (These are not % - If you receive 115% on an exam due to a curve you will only receive 100 pts. for the exam!) Final Exam 100 pts. Bonus Points 4% Class Attendance and assigned problems Grading Scale: A = 93% 100% B+ = 89% 92.9%: B = 80% - 88.9%: C+ = 77 79.9%: C = 70% - 76.9%: D+ = 65% - 69.9%: D = 60% 64.9%: F = 0 59.9%: Class Attendance: I will take attendance for about ten to twenty classes, so each class is worth between 0.20% and 0.10% You must be present in class to receive points. Notice: Bonus Points This is a % in that they are added to your total %. For example: A student attends all classes for a total of 4% Bonus. If the total from exams for this student where 87% the course grade would be calculated as 87% + 4% = 91%. So the final grade would be a B+. With no bonus points the grade would have been a B. Notes: 1. Missed exams count ZERO points, NO make-up exams. 2. If you have a question about your final grade you should see me as soon as possible. Exams and records are only kept for a period of 3 weeks after final grades are distributed. 3. All exams are Cumulative but will stress material covered since the last exam.
4. This course has a corequisite of Organic Chemistry I Laboratory. If you are NOT taking the laboratory it is your responsibility to obtain any relevant material from laboratory texts as referenced in the class lectures. Exams may cover material taken from laboratory experiments. This course has a prerequisite of General Chemistry II. You should not be in this course if you have not successfully completed General Chemistry II. 5. The lecture time for this course is 2:00 to 3:20 pm. i.e. one hour and 20 minutes. Depending on class size some of the time may be used for question/answer time. 6. If you are a student with a disability, and if you will be requesting accommodations, it is your responsibility to contact the Director of the Learning Differences Program. The Learning Differences Office will recommend any appropriate accommodations to your professor and his/her director. The professor and director will identify for you which accommodations will be arranged. Mercyhurst College provides a range of services to allow persons with disabilities to participate in educational programs and activities. If you desire support services contact the office of Learning Differences (814) 824-2450. The Learning Differences Office is located in room 314 Main. Questions Most Commonly Asked In or Outside of Class: What will the next exam cover? Exams cover all material covered in prior exams but stress the material from the last exam. Since this course follows General Chem I and II you are responsible for material covered in these courses but only as it relates to Organic Chemistry. Asking a question such as Is Chlorine a metal or a nonmetal? will only cause Dr. Williams to lose more hair from what little he already has! Questions on the exams will be taken from material discussed in lecture or from the assigned homework problems. Concepts discussed in your text which are NOT discussed in class will NOT be included on an exam. I missed the last class what did you cover?.if you miss a lecture it is your responsibility to get the notes from other students in the class. I will have to miss the next class.what will you cover?..consult the syllabus I may cover the topic mentioned, I may review problems, I may cover another topic if I feel it is appropriate best not to miss the class. I don t understand this could you help me? Organic Chemistry teaches you to think for yourself. I am always willing to help a student with a difficult concept but I will be asking you questions to see if you have studied the material first! A necessary condition for help outside the classroom is attendance of ALL lectures! I came late for this exam could I have more time? Exams start at the beginning of class and last for one class period. The later you come to class, the less time you will have to finish the exam. (In class question) Could you go over that concept again?.no problem. I am always happy to cover the concept again and again until you understand it! I have to miss the next exam, can I take a makeup exam?.. The best advice I can give you is NEVER NEVER miss an exam. When you request a makeup exam for whatever reason you should be aware of the following.
a. Makeup exams may be all essay type, all multiple choice or a mixture of both. i.e. reactions and synthesis in addition to multiple choice. This must be an entirely different exam, in fairness to the other students, because you will have had more time to study. b. This will be a more difficult exam, in fairness to the other students, because you may have seen the prior exam or heard discussion about the exam after it was given. c. This exam will not be curved even though the regular exam may be curved. How can one calculate a class average for one student? d. The exam will cover all material up to this exam. I.e. if you take this exam a week after the regular exam it will cover material through that week. Office Hours TBA Tentative Lecture Outline DATE TOPIC TEXT CHAPTER NOVEMBER 26,28,30 Introduction to Organic Chemistry Chapters 1,2 Functional Groups Chapter 3 DECEMBER 3,5,7 Organic Nomenclature Chapter 3 Organic Compounds: Alkanes and Cycloalkanes Chapters 3,4 10,12,14 Stereochemistry of Alkanes and Cycloalkanes Chapter 4 17,19,21 An Overview of Organic Reactions Chapter 5 JAUNUARY 7*,9,11 Alkenes : Structure and Reactivity Chapter 6 14,16,18 Alkenes : Reactions and Synthesis Chapter 7 Alkynes Chapter 8 (21**),23,25 Stereochemistry Chapter 9 28,30, Feb. 1 Alkyl Halides Chapter 10 FEBRUARY 4,6,8* Reactions of Alkyl halides Chapter 11 11,13, Sturcture Determination: MS and IR Chapter 12 Structure Determination NMR Chapter 13 Final Exam See Final Exam Schedule * Exams ** Martin Luther King Day Observed - No Class