CHEM 26100-LM 50419

SPRING 2016

ORGANIC CHEMISTRY I

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Dr. Valeria Balogh-Nair

Professor of Chemistry & Biochemistry Office: MR 1215 Office hours: Lectures: Recitations: Prerequisites: Hours/Credits:

Phone: 212-650-8340

[email protected]

Tuesday/Thursday 12:00 -2:00 PM or by appointment Tuesday/Thursday from 10:00 -11:45 AM Wednesday 7:30 - 9:20 PM (0 credits) Chem 104.01 (a grade of C or higher is required) 4 hours lecture per week, 3 credits

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TEXTBOOK: Organic Chemistry by T.W.G. Solomons, C.B. Fryhle & S.A. Snyder, 11th edition (ISBN 9781118133576) and Study Guide and Solutions Manual to Accompany Organic Chemistry 11th edition by T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder, Jon Antilla are available at the Wiley website (direct buy): http://www.wiley.com/WileyCDA/WileyTitle/productCd-EHEP002536.html Packages are available at the CCNY bookstore: One package ($140 net to bookstore 9781118566893) includes WileyPLUS (including the complete, interactive eBook), the Wiley eText (a downloadable, digital eText that can be used on multiple devices without an internet connection, and does not expire), and the complete printed Study Guide & Solution Manual in 3hole punched format. Another package available ($145 net to bookstore 9781118566893) include the complete printed text in binder-ready format, packaged with WileyPLUS (includes complete interactive eBook).

Molecular models of Dr. Darling’s are available in the bookstore and at http://www.darlingmodels.com/ KIT #1 ISBN 0-9648837-1-6). Lectures/Examinations Date Chapter February 2 1 February 4 1 February 11 2 February 16 2 February 18 3 February 23 3 February 25 4 March 1 4 MARCH 3 EXAM#1 (Chapters 1-4) March 8 5 March 10 5 March 15 6 March 17 6 March 22 7 March 24 7 March 29 8 March 31 8 April 5 review APRIL 7 EXAM #2 (Chapters 5-8) April 12 9 April 14 9 April 19 10 April 21 10 May 3 11 May 5 11 May 10 12 May 12 12 MAY 17 EXAM #3 (Chapters 9-12) FINAL EXAM (Chapters 1-12): The date will be set by the Registrar.

2 COURSE OBJECTIVES: This course is the first of a two-semester sequence. The objective of the course is to provide introduction to organic chemistry, via discussion of reactivity, key reaction mechanisms, retro synthetic analysis, and structure determination via IR, NMR, and MS. The course strives to enhance critical thinking and problem solving skills.

TOPICS COVERED: 1. Bonding, Lewis and resonance structures, Formal charges, structural formulas, isomers, atomic/ molecular orbitals, orbital hybridization 2. Functional Groups, Intermolecular Forces, IR Spectroscopy 3. Curved Arrow notation, Bronstead-Lowry & Lewis Acids/Bases, Nucleophiles/Electrophiles, Carbocations/Carbanions, Acid/Base reaction mechanism. 4. Alkanes/Cycloalkanes: Nomenclature & IUPAC rules, conformational analysis via Newman projection formulas. Chair/Boat forms of cyclohexanes and disubstituted cyclohexanes. Cis-Trans isomers and conformational structures of disubstituted cyclohexanes, Index of hydrogen deficiency & constitutional isomers. 5. Stereochemistry-Chiral Molecules Stereoisomers: Enantiomers & Diastereomers, (R) and (S) Configurations, Optical Activity Molecules with more than one stereocenter, Fischer projection formulas, 6. Nucleophilic Substitution & Elimination Reactions: Alkyl Halides Mechanism and stereochemistry of SN1 and SN2 reactions. Factors affecting the rate of SN1 and SN2 reactions. Synthesis using SN2 reactions. Mechanism of E1 and E2 reactions. Substitution versus elimination. 7. Alkenes & Alkynes I: Properties & Synthesis, Elimination Reactions of Alkyl Halides. (E)-(Z) system for alkene diastereomers. Synthesis of alkenes via Dehydrohalogenation of alkyl halides, acid-catalyzed dehydration of alcohols, and hydrogenation of alkynes. Carbocation rearrangements. Acidity of terminal alkynes. Synthesis of Alkynes. Retrosynthetic analysis. 8. Alkenes & Alkynes II: Addition Reactions. Addition of electrophiles: Markovnikov addition of HX, H+/H2O, Oxymercuration-demercuration. AntiMarkovnikov addition of water in Hydroboration/Oxidation. Stereospecific, anti addition of bromine, and HOX to alkenes. Syn-hydroxylation of alkenes, Ozonolysis of alkenes. Electrophilic additions to alkynes. 9. 1H-NMR spectroscopy, 13C-NMR spectroscopy, EI-MS spectroscopy, Structural elucidation employing a combination of IR, NMR and MS. 10. Radical Reactions Halogenation of methane and higher alkanes. Stability of radicals and the Hammond-Leffler postulate. Anti-Markovnikov addition to alkenes. 11. Alcohols & Ethers/Synthesis and Reactions Alcohols from alkenes, Reaction of Alcohols with HX, PBr3, SOCl2, TsOH. Williamson synthesis of ethers. Epoxidation, acid and base catalyzed opening of epoxides. 12. Alcohols from Carbonyl Compounds, Oxidations & Reductions. Organometallic Compounds. Formation of Grignard reagents and lithium reagents. Grignard synthesis of alcohols via nucleophilic addition to carbonyl compounds, and by opening of epoxides with Grignard reagents.

COURSE OUTCOMES What you should know: • Lewis structures, resonance forms, acid/base theories, orbital hybridization constitutional isomers, cis/trans isomers, IUPAC nomenclature • Newman and Fischer projection formulas. cycloalkane conformations • Stereochemistry: Recognize and write structures for chiral and achiral molecules, (R) and (S) configurations, enantiomers, racemates, diastereomers, meso compounds • Mechanism of SN1, SN2, E1 and E2 reactions. Predict the products of the substitution and elimination reactions including stereochemistry. • Predict the products of carbocation rearrangements, dehydration, dehydrohalogenation and dehalogenation reactions.

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Predict the products of additions, oxidations, reductions and cleavages of alkenes, including regiochemistry and stereochemistry. Acetylide ions in the synthesis of alkynes. Predict the products of additions, oxidations, reductions of alkynes. Predict the products of hydration, hydroboration, and hydroxylation of alkenes. Use Grignard reagents for the synthesis of alcohols. Reaction of alcohols and pinacol rearrangement of diols. Predict the mechanism and products of radical reactions Interpret infrared, mass, 1H NMR and 13C-NMR spectra.

ATTENDANCE POLICY Students are expected to attend every class session of each course in which they are enrolled and to be on time. An instructor has the right to drop a student from a course for excessive absence. Students are advised to determine the instructor’s policy at the first class session. They should note that an instructor may treat lateness as equivalent to absence. No distinction is made between excused and unexcused absences. Each instructor retains the right to establish his or her own policy, but students should be guided by the following general College policy: In courses designated as clinical, performance, laboratory or field work courses, the limit on absences is established by the individual instructor. For all other courses, the number of hours absent may not exceed twice the number of contact hours the course meets per week. When a student is dropped for excessive absence, the Registrar will enter the grade of WU.

Any student who misses five classes will be dropped from the course with a WU grade. Do NOT attend this class if you are not registered into CHEM 26100 Section LM (50419) Attend class to benefit from the problem solving sessions/quizzes incorporated into the lectures. COURTESY POLICY Noise, excessive chatter, use of flash light, and unauthorized electronic equipment is not allowed in the classroom. DISABILITY POLICY In compliance with CCNY policy and equal access laws, appropriate academic accommodations are offered for students with disabilities. Students must first register with The AccessAbility Center for reasonable academic accommodations. The AccessAbility Center is located in the North Academic Center, Rm. 1/218. Tel: (212) 650-5913. Under The Americans with Disability Act, an individual with a disability is a person who has a physical or mental impairment that substantially limits one or more major life activities. If you have any such issues, visit the AccessAbility Center to determine which services may be appropriate for you. EXAMS & GRADING POLICY There will be three 90 minute exams during the semester of which you should take at least two. There will NOT be any Make-up exams. If you take all three exams your lowest exam score will be dropped while computing your grade. If you take only two of the 90 minute exams, both scores will count towards your grade. Missing an exam will result in receiving a zero grade for that particular exam and thus dropping that grade. These three exams will account for 60% towards your final grade, the Final Examination for 40%. A make-up for the Final Examination will be offered only under compelling circumstances (see under Department INC grade policy). The Final Examination will cover ALL CHAPTERS (1-12) studied. The final grade is calculated as follows: Best two scores of the three in-class examinations Final Exam

(60%) (40%)

In class BONUS points (maximum 5 Points) will be added to your total when computing your grade. For example, your total is 87/100, but you earned 3 BONUS Points, therefore your total is 90/100, and you achieved a grade of A.

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The conversion from points to letter grades is done as follows:

95-100 : 90-94 : 88-89 : 86-87: 80-85: 78-79:

A+ A AB+ B B-

76-77: 70-75: 68-69: 60-67: 0-59:

C+ C CD F

TEXTBOOK PROBLEMS: The assigned problems are a very important part of the course. You are responsible for ALL problems, within and at the end of each chapter. If you can do the problems, you should do well on the exams.

DEPARTMENT “INC” GRADE POLICY: Makeup exam for INC grades in Chemistry courses will be completed no later than two weeks after the end of classes. INC may be assigned to students who have a passing grade in the course but who are unable to take the final examination. A passing grade is computed by averaging all examinations / assignments which include a zero grade for missed examinations. A student must have a very good reason (such as a conflict with another scheduled examination, death of spouse, injury sustained in a catastrophic incident, etc., and {proof is required}) for missing the scheduled final exam and be given an INC grade. If the reason is not forthcoming, then a letter grade of F should be assigned. An Incomplete Grade Agreement form must be signed by the Instructor before the student is allowed to take the makeup exam. Payment of a fee at the Bursar's office is required in order to take the makeup examination. The Registrar may waive the fee if the reason for granting an INC grade is conflict with another scheduled examination.

ACADEMIC INTEGRITY The CCNY policy on academic integrity will be followed in this course. The document can be found at: http://www1.ccny.cuny.edu/current/integrity.cfm In addition, the Policy on Academic Integrity can be found in the Undergraduate Bulletin 2007-2009 in Appendix B.3 on page 312. All students must read the details regarding plagiarism and cheating in order to be familiar with the rules of the college. Cases where academic integrity is compromised will be prosecuted according to these rules. Allowing the student to do extra work after the final grade has been awarded: A student offers the instructor many reasons why the academic work submitted during the semester was not an adequate representation of his/her grasp of the course content. The instructor agrees to read the extra work and change the grade, if the work is warranted. Although similar to the above situation in that the student is being allowed to do work after the course is over, this scenario differs in its details. This arrangement presents two problems: firstly, it is unfair to those students who have not been offered such an opportunity and have completed coursework sufficiently and on time; secondly, it circumvents the mandated appeals process. Consequently, it is a violation of the academic policy of the school. Allowing the student to negotiate a grade: A student does no extra work after the award of a final grade, yet he/she bases a campaign for a higher grade on the sheer force of an argument. The higher grade may be wrested from the professor by the brilliance of the student’s debate or by the latter’s subtle but persistent erosion of the instructor’s strength of refusal. As the instructor is paid for his/her expertise in a field, they are expected to exercise competency in his/her determination of an appropriate grade for a student. Consequently, it is a violation of the academic policy of the school.

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RECITATION for CHEM 26100 Section LM Instructor:

Christopher Kreiter Wednesdays 7:30 PM – 9:20 PM in MR2 What is RECITATION ? Recitations are problem solving sessions devoted to the study and practice of organic chemistry under the guidance of the recitation leader. It is to your best interest to attend, as each session is carefully planned by the recitation leader. Attendance at recitations is free, and it is not mandatory. However, participating in the recitations will help you to solve the assigned problems. This, in turn will help you to succeed in the course by honing your problem solving ability. What is expected of me ?  It is assumed that you have read the assigned chapter before the recitation session • Students participating in the recitation must be present for the entire session. Latecomers will not be allowed to participate. • If you miss more than 2 sessions, you will be dropped. Please bring your textbook, solutions manual, molecular modeling kit to each session.

Detailed instructions will be given by the recitation leader