CVHS Organic Chemistry Syllabus Teacher: Mrs. Katrina Cantrell Email: kcantre1@houstonisd.org Email is the best way to reach me! (Note “1” not “l”) SUPPLIES: A Binder for Your Notes: It is your responsibility to keep up with your notes and other handouts – if you lose them, you will need to print out another copy from a classmate. A binder dedicated to this course is highly recommended! Closed-Toe Shoes on lab days. If you do not have closed-toe shoes on lab day you will receive a zero for that activity! *Extra credit will be given on the lab safety quiz for a box of facial tissues, one ream of printer paper or a double roll of paper towels. GRADING: Student grades will be determined by the following method: 40% Test and/or Projects 20% Quizzes 20% Homework 20% Labs CVHS RETAKE POLICY: In accordance with Senate Bill 2033 Carnegie Vanguard abides by the following retake policy: Not to exceed 2 retakes per grading cycle Maximum retake score is 70, (score of 70 to 100 = 70) The highest grade between the original and the retake is counted. The student, not the parent, must request the retake in writing (per teacher procedure in class syllabus) Student must request the retake within 24 hours and complete the retake within one week of grade posted Retakes are for in-class assessments, such as quizzes and/or tests only. A reading quiz (reading check) is an extension of homework and is not eligible for a retake. Student must fill out a retake form. If there are multiple retakes in the same day, it is the student’s responsibility to reschedule with the teacher in advance No shows counts as a taken retake Final Exams are not eligible Missing assignments fall under teacher’s late policy not campus retake policy. ACADEMIC HONESTY: If a student is caught cheating on tests, homework, or labs the student will receive a zero on that assignment and their parents will be called or e-mailed explaining the situation. Students will also be referred to the office and will receive a discipline referral according to HISD policy. LATE WORK: Assigned work must be turned in by the due date. Any late assignments may be turned in by 8:30 am the following school day, and will suffer a 30% penalty. TUTORIALS: All tutorials will be held during the SSEP period from 8:30 until 9:00 daily. The SSEP pass must be obtained before school, after class or during lunch for the next SSEP period. Tutorials are also available during lunch or before school. Please make an appointment for before school or lunch tutorials. TARDINESS: The student must be in their seat when the bell rings or they will be considered tardy. If the student arrives to the classroom after the bell has rung, the student must sign the Tardy Sheet on the table by the door. On the fourth tardy they will be assigned Lunch Detention in my room for the following day. After the fifth tardy the student will be referred to the Administration. ATTENDANCE: If the student is absent it is their responsibility to gather the assignments that they have missed on the day of their return. If they missed an exam or lab, they must schedule a make-up exam. Please keep in mind that the format of the make-up is at the teacher’s discretion. The student must complete and turn in the make-up work in a timely manner, usually the number of days missed plus one. CLASS RULES: I expect my students to abide by four very simple rules in my classroom: “Be Polite, Prepared, Punctual and Productive.” (Course Description and Course Outline Follow) Carnegie Vanguard High School Organic Chemistry Syllabus Pre-requisite: pre-AP Chemistry at a minimum, Advanced Placement Chemistry preferred Course Description: This course is designed to provide a fundamental overview of organic chemistry to students interested in pursuing a career in the sciences. Upon successful completion of this class, students will understand the relationship between structure and function of molecules, the major classes of reactions, reaction energetics and mechanisms, synthesis of organic compounds, and how to determine structure via various spectroscopic techniques. Several themes are prevalent in each unit of study: nomenclature, chemical and physical properties, structures, mechanisms, common molecules, and the diversity of organic molecules in plants, bacteria, and animals. Many chapters in our textbook also integrate the societal, pharmaceutical or industrial importance of specific compounds. An important aspect of any chemistry class is laboratory experience. Students will participate in weekly micro-scale labs in which they will safely perform a variety of experiments. Lab results will be recorded in students’ lab notebooks, and formal lab reports will be completed. Learning Outcomes: Upon completion of this class, students will be able to predict bonding and three-dimensional structure, including chirality of organic compounds. Students will be able to predict the reactivity of specific functional groups, and construct efficient, simple mechanistic pathways for the synthesis of a given compound. Recommended Texts and Materials: John McMurray, “Organic Chemistry,” Eighth Edition, 2012 Tom Russo and Mark Meszaros, Vial Organic Chemistry, 1996 Molecular Model Kit Course Outline: 1. Structure and Bonding Review of general chemistry, atoms, bonds, and molecular geometry 2. Polar Covalent Bonds, Acids and Bases Electronegativity, formal charge, resonance structures, definitions and strengths of acids and bases, calculating Ka, organic acids and bases 3. Alkanes and Stereochemistry functional groups, isomers, alkyl groups, IUPAC naming rules, common names, properties of alkanes, conformations and Newman projections, fuels and petroleum refining 4. Cycloalkanes and Their Stereochemistry Naming, cis-trans isomerism, stability, ring strain, polycyclic molecules 5. Stereochemistry at Tetrahedral Centers Chirality, optical activity, rules for specifying R and S configurations, diastereomers 6. Overview of Organic Reactions Major classes of organic reactions, introduction to mechanisms, radicals, polar reactions, equilibria, rates and energy changes, bond dissociation energies, energy diagrams 7. Alkenes: Structure and Reactivity Carbon-carbon double bonds, electrophilic addition reactions, industrial preparation and use of alkenes, naming, stereoisomerism, the Hammond Postulate, carbocations. 8. Alkenes: Reactions and Synthesis Elimination reactions, halogenation, addition of water, reductions and oxidations of alkenes, synthesis of cyclopropane, chain-growth polymers, reaction stereochemistry 9. Alkynes: An Introduction to Organic Synthesis Naming, preparation of alkynes by elimination reactions of dihalides, addition reactions of HX and X2, hydrations, reductions, oxidative cleavage, organic synthesis 10. Organohalides Names and properties of alkyl halides, their preparation from alkanes and alkenes, resonance stabilization, Grignard reagents, organometallic coupling 11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations SN2, SN1, biological substitution reactions, Zaitsev’s Rule, E2 reaction and deuterium isotope effect, E2 reactions and cyclohexane conformations 12. Structure Determination: Mass Spectometry and Infrared Spectroscopy Determining the structures of new molecules is critical to progress in chemistry and biochemistry fields. This course will give an overview of the various types of spectroscopy available. Topics to be introduced will include: Spectroscopy and the electromagnetic spectrum, mass spectrometry, infrared spectroscopy, X-ray crystallography, and nuclear magnetic resonance. 13. Structure Determination: Nuclear Magnetic Resonance Application to small molecule C-H mapping 14. Conjugated Compounds and Structure Determination Stability of conjugated dienes, the Diels- Alder cycloaddition reactions, diene polymers, natural and synthetic rubber, conjugation, color, and the chemistry of vision 15. Benzene and Aromaticity Structure and stability of benzene, the Huckel 4n+2 rule, pyridine and pyrrole, polycyclic compounds * Aspirin, NSAIDS, and COX2 inhibitors 16. The Chemistry of Benzene: Electrophilic Aromatic Substitution Bromination, the Friedel-Crafts reaction, substituent effects, oxidation of aromatic compounds, reduction reactions, nucleophilic aromatic substitutions *Combinatorial Chemistry: Using robots to do organic chemistry 17. Alcohols and Phenols Naming, properties, preparation, alcohols from carbonyl compounds, reduction, Grignard reaction, phenols and their uses spectroscopy 18. Ethers and Epoxides; Thiols and Sulfides Naming, properties, reactions of ethers, acidic cleavage, Claisen rearrangement, ring opening, spectroscopy 19. Carbonyl Compounds General reactions, preparation, nucleophilic addition reactions of aldehydes and ketones, nucleophilic addition of amines, the Wolff-Kishner reaction, the Wittig Reaction, spectroscopy 20. Carboxylic Acids and Nitriles Naming, structure and properties, acidity, preparation, reactions, HendersonHasselbalch Equation 21. Carboxylic Acid Derivatives Nucleophilic acyl substitution reactions, chemistry of acid halides, esters, amides, thioesters, and acyl phosphates, polyamides, and polyesters, step-growth polymers * Beta- Lactam antibiotics 22. Carbonyl Alpha-Substituion Reactions Keto, enol tautomerism, mechanism of alpha-substitution reactions, alphahalogenation of aldehydes and ketones, alpha bromination of carboxylic acids *Barbiturates 23. Carbonyl Condensation Reactions The Aldol reaction, Claisen Condensation reaction, other biological carbonyl condensations 24. Amines and Heterocyclic Compounds Naming, structure and properties, basicity, synthesis, Hofman Elimination, reduction reactions 25. Biomolecules: Carbohydrates Classification, Fischer projections, cyclic structures of monosaccharides, polysaccharides and their synthesis 26. Biomolecules: Amino acids, peptides, and proteins 27. Biomolecules: Lipids, soaps, detergents, phospholipids The lab experiments to be performed are: 1. Melting Point Determination 2. Boiling Point Determination 3. Isolation of Chlorophyll from Spinach 4. Isolation of Cinnamaldehyde from Cinnamon Sticks 5. Hydrolysis of Starch 6. Formation of an Alkene 7. Formation of t-Butyl Chloride 8. Mixed Aldol Condensation Reaction 9. Preparation of Iodoform 10. The Formation of an Ester 11. The Formation of a Useful Ester: Aspirin 12. Oxidation of Benzaldehyde