Chemistry 262: Organic Chemistry II Winter 2018 The second of a three quarter sequence in organic chemistry for university transfer, intended primarily for science majors, and those fulfilling requirements for professional health science careers such as medicine, dentistry, and pharmacy. Topics include structure, nomenclature, physical properties, synthesis, and detection of the principal structural motifs of organic chemistry. Lab included. The course requires successful completion of Chem& 261 (Organic Chemistry I) as a prerequisite Instructor: Shane Hendrickson Office: Eller-Fox, Room 3009 Website: http://commons.wvc.edu/shendrickson Phone: (509) 682-6747 e-mail: shendrickson@wvc.edu Official Office hours: M-Th 9 10 am, F 11 am - noon 1 Required Texts: Organic Chemistry, 6 th edition, Marc Loudon and Jim Parise, Macmillan (2016) The Organic Chem Lab Survival Manual, 10 th edition, James W. Zubrick, Wiley (2016) Recommended Texts: A Small Scale Approach to Organic Laboratory Techniques, 3rd ed, Pavia et. al., Brooks/Cole (2011) Time & Location Lecture M, T, W, Th from 11:00 to 11:50 am, Eller-Fox Rm 3018 Laboratory Th from 1:00 to 5:00 pm, Eller-Fox Rm 3018 1 But generally available please see my schedule posted on the commons website
Grading: The Grading for Chem 261 will be as follows 3 Examinations: 3 exams(90 points/exam) = 270 points (36 %) Final Exam = 150 points (20 %) 10 Laboratory Experiments 2 : 10 labs(15 points/lab) = 150 points (20 %) 4 Quizzes, lowest dropped: 3 quizzes(30 points/quiz) = 90 points (12 %) 4 Homework: 4 HW(15 points/hw) = 60 points (8 %) 3 Group Exercises: 3 GE(10 points/ge) = 30 points (4 %) Total graded 3 points = 750 Grades will be assigned as a percentage of total points possible, as follows: % Grade % Grade % Grade % Grade >93.0 A 81.0-84.9 B 69.0-72.9 C 57.0-60.9 D 89.0-92.9 A- 77.0-80.9 B- 65.0-68.9 C- < 56.9 F 85.0-88.9 B+ 73.0-76.9 C+ 61.0-64.9 D+ As may be noted from the above, the course is not graded on a Gaussian distribution. I reserve the right to normalize the grades upward if the class average falls below a C+. However, the more likely occurrence will be the assigning of additional problems for extra credit. Schedule of Examinations: Part I: Alcohols, Ethers, and Sulfur Analogs; In Depth Investigation into the Chemistry of Alkyl Halides; Intermolecular Interactions in Depth Thursday 1/25 Part II: In Depth Investigation into the Chemistry of Alcohols, Ethers, and Sulfur Analogs Thursday, 2/15 Part III: Stereochemistry; Cyclic Compounds & Reaction Stereochemistry; Intermolecular Interactions in Depth Wednesday, 3/01 Part IV: Alkynes and Conjugated Systems [Emphasized] Cumulative Final Examination TBD as Best Fits Schedule 2 You must complete the laboratory experiments to pass the class. If you miss more than 1 lab you must withdraw from the course (drop deadline 2/22) 3 Non-extra credit
Make-up Examinations & Late Work Policy Make-up exams will be considered only if you approach me before the scheduled exam with an exceptional, documentable excuse. Documentation is mandatory before a makeup examination will be provided. If you miss an exam and have not notified me beforehand you will receive a zero for that exam. As one quiz is dropped, make-up quizzes will not be provided Due to time constraints, make-up examinations will not be given for poor test performance. Late work is assessed a 20 % penalty for each calendar day it is late; that is, a 10 point assignment turned in 3 days late has a maximum value of 4 points. After 5 days the assignment has no point value. Any assignment turned in after the assignment has been returned to the rest of the class has no point value Labs are normally due at the beginning of the following lab session. Labs not turned in at the start of the session will be assessed a 5 % penalty Excusal from Final In the event a student need only pass the final with a C to receive an A for the course, he or she is excused from taking the final examination. Since the total number of graded (non-extra credit) points in the course is 750,.93(750) = 697.5 points are required for an A. As a C passing score for the final is.70(150) = 105, 697.5 105 = 592.5 points accumulated prior to the final is required to have the examination waived. While this corresponds to (592.5/600) = 98.7 % of graded points, opportunities for extra credit exist and having the final waived is a possibility for the dedicated student. All other work must be turned in prior to the final and the 4 th and final quiz must receive a passing mark of > 70 % to exercise this option. Behavior You are primarily students who have elected to pursue professional careers in the health sciences. As such, little needs be said concerning behavior since the expectation is you will conduct yourselves accordingly. You should be mindful of creating distractions, as they only impede your fellow students opportunity for success. Please note that questions are never considered distractions, but must be limited to the topic at hand. As a courtesy to others, cell phones or other portable electronic devices should be turned off, or switched to vibrate in the event an emergency call is anticipated. Laptop computers or similar devices capable of accessing the day s lecture and taking notes are encouraged, but only as a learning aid for the discussion at hand. Students using laptops for anything but the day s topic will be assessed a 5 point penalty. Texting in class is not allowed and students found doing so will also be penalized 5 points no exceptions. Cheating will not be tolerated under any circumstances. My standing policy is to give a score of 0 for any exam a student is caught cheating on. Therefore, since each exam is worth 12 % of the total points (20 % for the final), and the division of letter grades roughly corresponds to 10% of the total points available, cheating will cost you no less than one letter grade, and likely 2. Disabilities Students with disabilities who believe they may need academic adjustments, auxiliary aids or services to fully participate in course activities or meet course requirements are encouraged to register with Disability Support Services, Rm 2133 in Wenatchi Hall. (509) 682-6854.
Tentative Schedule of Lecture Topics Week 1 Wednesday, 1/03 Thursday, 1/04 Organic Chemistry I Review Organic Chemistry I Review Lab Session 1: Organic Chemistry I Review Last Quarter s Final Revisited Part I: Alcohols, Ethers, and Sulfur Analogs; In Depth Investigation into the Chemistry of Alkyl Halides; Intermolecular Interactions in Depth Week 2 Monday, 1/08 Nomenclature Extended (8.1, 8.2) HW 1 Out Tuesday, 1/09 Intermolecular Interactions and Their Relationship to Melting Point, Boiling Point, and Solubility (8.3-8.5) Wednesday, 1/10 Heterogeneous Intermolecular Interactions (8.6) Thursday, 1/11 Applications of Solubility and Solvation Principals; Strength of Noncovalent Intermolecular Interactions (8.7, 8.8) Lab Session 2: Pharmaceutical Compounding Isolation of a Biologically Active Plant Alkaloid and Preparation of a Drug Dosage Form, Part I Week 3 Monday, 1/15 Martin Luther King Holiday NO CLASS Tuesday, 1/16 Overview of Nucleophilic Substitution and -Elimination Reactions; Equilibrium and Reaction Rate Considerations in Nucleophilic Substitution Reactions (9.1-9.3) Wednesday, 1/17 The S N 2 & E2 Reactions (9.4, 9.5) Thursday, 1/18 The S N 1 & E1 Reactions; Summary of Substitution and Elimination Reactions of Alkyl Halides (9.6, 9.7) Lab Session 3: Pharmaceutical Compounding Isolation of a Biologically Active Plant Alkaloid and Preparation of a Drug Dosage Form, Part II
Part II: In Depth Investigation into the Chemistry of Alcohols, Ethers, and Sulfur Analogs Week 4 Monday, 1/22 Introduction to Organometallic Compounds: Organolithium and Grignard Reagents; Carbenes and Carbenoids; Industrial Preparation and Use of Alkyl Halides (9.8-9.10) Tuesday, 1/23 Quiz 1 Wednesday, 1/24 The Brønsted-Lowry view of Alcohols and Thiols; Dehydration of Alcohols; Reaction of Alcohols with Hydrogen Halides (10.1-10.3) HW 2 Out Thursday, 1/25 Examination I Lab Session 4: The Grignard Synthesis of Benzoic Acid from Bromobenzene Week 5 Monday, 1/29 Tuesday, 1/30 Alcohol Derived Leaving Groups; Summary of Alcohol to Alkyl Halide Conversions; Organic Oxidations and Reductions Oxidation of Alcohols to Aldehydes, Ketones, and Carboxylic Acids (10.4 10.7) Biological Oxidation of Ethanol; Stereochemical Group Relationships; Octet Expansion and the Oxidation of Thiols (10.8 10.10) Wednesday, 1/31 Synthesis of Alcohols Revisited; Planning a Synthesis Retrosynthetic Analysis; Production and Use of Methanol and Ethanol (10.11 10.13) Thursday, 2/01 Group Exercise 1 Lab Session 5: Derivatization of the Grignard Product Formation of Ethyl and Propyl Benzoate from Benzoic Acid
Week 6 Monday, 2/05 Tuesday, 2/06 Wednesday, 2/07 Thursday, 2/08 Basicity of Ethers and Sulfides; Synthesis of Ethers and Sulfides; Synthesis of Epoxides (11.1 11.3) Cleavage of Ethers; Nucleophilic Substitution Reactions of Epoxides; Preparation and Oxidative Cleavage of Glycols (11.4-11.6) Oxonium and Sulfonium Salts; Intramolecular Reactions and the Proximity Effect; Oxidation of Ethers and Sulfides (11.7-11.9) Advising No Classes Lab Session 6: Conversion of Borneol to Isoborneol via Camphor Part III: Infrared Spectroscopy and Mass Spectrometry Revisited; Nuclear Magnetic Resonance Spectroscopy in Depth Week 7 Monday, 2/12 The 3 Fundamental Operations of Organic Synthesis; Chiral Synthesis via Asymmetric Epoxidation (11.10-11.11) Tuesday, 2/13 Quiz 2 Wednesday, 2/14 Introduction to Spectroscopy the Nature of EMR; Infrared Spectroscopy Revisited (12.1 12.5) Thursday, 2/15 Examination II Lab Session 7: Use of NMR, GC/MS, and UV/Vis. Simple Unknown Identification Week 8 Monday, 2/19 Presidents Holiday NO CLASS Tuesday, 2/20 Introduction to Mass Spectrometry (12.6) Wednesday, 2/21 Thursday, 2/22 Introduction to Proton NMR; The Physical Basis of NMR; Interpreting the Spectrum Chemical Shift and Peak Integration (13.1 13.3) Spin-Spin Coupling and Peak Splitting; Complex NMR Spectra; Use of 2 H in Proton NMR; Characteristic Functional Group absorptions (13.4-13.7) Lab Session 7: Fun with Unknown Identification Utilizing IR, NMR, and MS Spectral Data Last to Withdraw or Change to Audit
Part IV: The Chemistry of Alkynes; Conjugated Alkenes UV/Vis Spectroscopy, Dienes and the Diels-Alder Reaction, Resonance and an Introduction to Aromatic Systems Week 9 Monday, 2/26 NMR of Dynamic Systems; 13 C NMR and Other Possibilities; Solving Structures with NMR Guiding Principles; The NMR Spectrometer; MRI (13.8 13.12) Tuesday, 2/27 Quiz 3 Wednesday, 2/28 Structure and Bonding in Alkynes; Nomenclature of Alkynes; Physical Properties of Alkynes (14.1 14.3) Thursday, 3/01 Examination III Lab Session 8: Carbon to Carbon Bond Formation via the Deprotonation of Terminal Alkynes Week 10 Monday, 3/05 Tuesday, 3/06 Wednesday, 3/07 Introduction to Alkyne Addition Reactions; Conversion of Alkynes to Aldehydes and Ketones; Reduction of Alkynes (14.4 14.6) Acidity of Terminal Alkynes; Incorporating Alkynes into Synthetic Strategies; Pheromones; Occurrence and Use of Alkynes (14.7 14.10) Structure and Stability of Dienes; UV-Vis & Fluorescence Spectroscopy (15.1 15.2) Thursday, 3/08 The Diels-Alder Reaction (15.3) Lab Session 9: The Diels-Alder 4+2 Cycloaddition between Cyclopentadiene and Maleic Anhydride Week 11 Monday, 3/12 Group Exercises 2 & 3 Tuesday, 3/13 Addition of Hydrogen Halides to Conjugated Dienes; Diene Polymers; Resonance Revisited (15.4 15.6) Wednesday, 3/14 Introduction to Aromatic Compounds; Noncovalent Interactions of Aromatic Rings (15.7 15.8) Thursday, 3/15 Quiz 4 Lab Session 10: A Green Friedel-Crafts Acetylation of Ferrocene
Week 12 Monday, 3/19 Tuesday, 3/20 Wednesday, 3/21 Final Examination: Listed as 10:30 a.m. to 12:30 p.m. TBD as Best Suits Everyone s Schedules Finals Finals and then Spring Break!!