The City College of New York
Department of Chemistry
Chemistry 26100: Organic Chemistry I
Section: GH
(212) 650 – 8386
Office Location: MR-1018
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Catalog Description:
An introduction to the chemistry of carbon compounds, current interpretation of the reactions and properties of these compounds.
Prerequisites: Chem 10401 or 10400
Hours/Credits: 4 per week, 4 hours lecture, 1 hour recitation, 3 credits
Textbook: Organic Chemistry by L.G. Wade, 6th ed., Prentice Hall, 2006.
ISBN 0-13-147871-0
Course objectives:
This course is the first of a two-semester sequence. The objective of the course is to provide an introduction to organic chemistry, via discussion of reactivity, key reaction mechanisms, retrosynthetic analysis, and structure determination via IR, NMR, and MS spectroscopies. The course strives to enhance the critical thinking and the problem solving skills of the students.
After completing this course
students should be able to:
1. Draw Lewis structures, line-angle formulas, and to use resonance forms to predict stabilities. Predict relative acidities and basicities based on structure, bonding, and resonance of conjugate acid-base pairs.
2. Predict the hybridization and geometry of an atom in a molecule, identify polar and nonpolar molecules, and predict which ones can engage in hydrogen bonds. Identify constitutional isomers and stereoisomers, identify common functional groups.
3. Name alkanes and cycloalkanes, predict the most stable conformations, write Newman projection formulas. Explain ring strain in cycloalkanes. Draw cis and trans isomers of cycloalkanes, draw accurate cyclohexane conformations, and predict the most stable conformation of substituted cyclohexanes.
4. Explain the mechanism of the free radical halogenations of alkanes. Based on the selectivity of halogenations, predict the product of halogenation of an alkane. Use energy diagrams to discuss transition states, activation energies, intermediates, and the rate determining step in a multistep reaction. Use the Hammond postulate to predict whether a transition state will be reactant-like or product-like. Describe the structures carbocations, carbanions and carbenes.
5. Classify molecules as chiral or achiral, and identify mirror planes of symmetry. Assign (R) and (S) configurations. Identify enantiomers, diastereomers and meso compounds. Draw correct Fisher projections of asymmetric carbon atoms, and assign (R) and (S) configurations from Fisher projections.
6. Draw the mechanism and energy profiles of SN1, SN2, E1 and E2 reactions. Predict the products of SN1, SN2, E1 and E2 reactions, including stereochemistry. Predict and explain the rearrangement of carbocations. Predict whether a reaction will be first-order or second-order, and predict the predominance of substitution or elimination. Use the ZaitsevŐs rule to predict major and minor elimination products.
7. Use the (E)/(Z) and cis/trans systems to name alkenes. Propose mechanisms to predict the products in dehydration, dehydrohalogenation and dehalogenation reactions. Predict the E2 elimination products including stereochemistry on cyclohexene systems. Propose effective single-step and multi-step syntheses of alkenes.
8. Predict the products of additions, oxidations, reductions and cleavages of alkenes, including regiochemistry and stereochemistry. Propose logical mechanisms to explain the observed products of alkene reactions, including regiochemistry and stereochemistry. Use retrosynthetic analysis to solve multistep synthesis problems with alkenes as reagents, intermediates or products.
9. Show how to use acetylide ions in the synthesis of alkenes. Predict the products of additions, oxidations, reductions and cleavages of alkynes. Use alkynes as starting materials and intermediates in one-step and multistep syntheses.
10. Show how to convert alkenes, alkyl halides, and carbonyl compounds to alcohols. Predict the alcohol products of hydration, hydroboration, and hydroxylation of alkenes. Use Grignard and organolithium reagents for the synthesis of primary, secondary and tertiary alcohols with the required carbon skeletons.
11. Predict the products of the reaction of alcohols with oxidizing reducing agents, and alkoxide ions. Predict the products of pinacol rearrangement and periodate cleavage of glycols. Use retrosynthetic analysis to propose effective single-step and multistep syntheses of compounds using alcohols as intermediates.
12. Given an IR spectrum, identify the reliable characteristic peaks. Predict stretching frequencies of common functional groups. Identify functional groups from IR spectra. Determine molecular weight from mass spectra. Use MS to recognize the presence of Br, Cl, I, N, and S atoms. Predict the major fragmentation pathways of alkanes, alkenes, alkynes, alcohols, ethers and amines. Use the fragmentation pattern to determine whether a proposed structure is consistent with the mass spectrum.
13. Given a structure, determine which protons are chemically equivalent and which are not. Given the chemical shifts, suggest likely types of protons. Use the integration to determine the relative numbers of different types of protons. Use proton spin-spin coupling patterns to analyze the 1H NMR spectra. Predict the approximate chemical shifts of carbons in a given compound. Use the off-resonance-decoupled 13C-NMR spectrum to determine the number of hydrogens bonded to a given carbon.
14. Use the information derived from the IR, MS and NMR spectra to propose a tentative structure for an unknown organic compound.
15. Work as part of a problem solving team to solve organic chemistry problems. The studentŐs ability to work as a team will be enhanced by solving problems in class and in the organic workshop. For example, arriving at the structure of an organic compound based on its reactivity and spectral data (IR, MS, NMR) is not unlike the diagnosis of a disease from patient history and clinical results (e.g. CAT and MRI scans).
16. Assess the impact of organic
chemistry in other fields. For example, discussion of laboratory oxidation
reactions will include highlights of important biological oxidations involved
in aging and apoptosis, and the discussion of halogenation reactions will
include learning about other chain reactions that yield natural and synthetic
polymers.
Topics covered:
1. Review of atomic structure, Lewis structures, ionic structures, resonance structures, bonding, formulas, acid/base theories.
2. Structure and properties of organic molecules.
3. Structure and stereochemistry of alkanes.
4. The study of chemical reactions (Key mechanism: Free radical halogenation).
5. Stereochemistry.
6. Alkyl halides: Nucleophilic substitution and elimination.
7. Structure and synthesis of alkenes.
8. Reactions of alkenes.
9. Alkynes.
10. Structure and synthesis of alcohols.
11. Reactions of alcohols.
12. Infrared spectroscopy and mass spectrometry.
13. Nuclear magnetic resonance spectroscopy.
Course schedule:
Section: GH
Lecture: Monday and Wednesday: 6:00 pm – 7:50 pm
Assessment tools:
The final grade is calculated as follows:
Best two scores of the three in-class examinations (60%)
Quizzes – Grade to be added to exams
Final Exam (40%)
* The lowest grade exam will be dropped. Missing an exam will result in receiving a zero grade for that particular exam and thus dropping that grade. There will not be any Make-up Exams.
TEXTBOOK: "Organic Chemistry" by L.G. Wade, Jr., Prentice Hall, Inc, 6th edition, 2006.
"Solution Manual" by J.W. Simek,/Wade Jr. Prentice Hall, Inc, 6th Edition., 2006.
Molecular models (Dr. DarlingŐs)
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.
EXAMS: There will be three 90 minute exams during the semester of which you should take at least two. 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, all scores will count. These three exams will account for 60% towards your final grade, the Final Examination for 40%. The date of the Final Examination will be set by the registrar, and will cover ALL CHAPTERS (1-13) studied.
Office Hours:
Monday: 11:00 am – 12:00 pm
Mondays: 4:00 pm – 5:00 pm
Wednesdays: 11:00 am – 12: 00 pm
Wednesdays: 4:00 pm – 5:00 pm
Or by appointment
Office is located in the science building in room 1018
Any student who misses more than four classes will be dropped from the course.
Academic integrity
The CCNY policy on academic integrity will be followed. Document is posted on the CCNY website (CUNY policy on academic integrity—link is at the bottom of the home page). Make sure you have read the details regarding plagiarism and cheating, in case you are not clear about the rules of the college. Cases where academic integrity is compromised will be prosecuted according to these rules.
Class Schedule
January 28th
Monday Chapter 1: Introduction and Review
January 30th
Wednesday Chapter 1: Introduction and Review
1.10 Structural Formulas, 1.11 Molecular Formulas and Empirical Formulas, 1.12 Arrhenius Acids and Bases, 1.13 Bransted-Lowry Acids and Bases, 1.14 Lewis Acids and Bases
Chapter 2: Structure and Properties of Organic Molecules
2.1 Wave Properties of Electrons in Orbitals, 2.2
Molecular Orbitals, 2.3 Pi Bonding, 2.4 Hybridization and Molecular Shapes, 2.5
Drawing Three-Dimensional Molecules
February 4th
Monday Chapter 2: Structure and
Properties of Organic Molecules
2.6 General Rules of Hybridization and Geometry, 2.7 Bond Rotation, 2.8 Isomerism, 2.9 Polarity of Bonds and Molecules, 2.10 Intermolecular Forces, 2.11 Polarity Effects on Solubilities, 2.12 Hydrocarbons, 2.13 Organic Compounds Containing Oxygen, 2.14 Organic Compounds Containing Nitrogen
February 6th
Wednesday Chapter 3: Structure and Stereochemistry of Alkanes
3.1 Classification of
Hydrocarbons, 3.2 Molecular
Formulas of Alkanes, 3.3 Nomenclature of Alkanes, 3.4 Physical Properties of Alkanes, 3.5 Uses and Sources of Alkanes,
3.6
Reactions of Alkanes, 3.7 Structure and
Conformations of Alkanes, 3.8
Conformations of Butane, 3.9
Conformations of Higher Alkanes
February 11th
Monday Chapter 3: Structure and Stereochemistry of Alkanes
3.10 Cycloalkanes, 3.11 cis-trans
Isomerism in Cycloalkanes, 3.12
Stabilities of Cycloalkanes; Ring Strain, 3.13
Cyclohexane Conformations, 3.14
Conformations of Monosubstituted Cyclohexanes, 3.15
Conformations of Disubstituted Cyclohexanes, 3.16 Bicyclic Molecules
February 13th
Wednesday Chapter 5: Stereochemistry
5.1 Introduction, 5.2 Chirality, 5.3 (R) and (S) Nomenclature of Asymmetric Carbon Atoms, 5.4 Optical Activity, 5.5 Biological Discrimination of Enantiomers, 5.6 Racemic Mixtures, 5.7 Enantiomeric Excess and Optical Purity, 5.8 Chirality of Conformationally Mobile Systems
February 18th
Monday ***
NO CLASS *** College Closed ***
PresidentŐs
Day
February 20th
Wednesday Chapter 5: Stereochemistry
5.9 Chiral Compounds without Asymmetric Atoms, 5.10 Fischer Projections, 5.11 Diastereomers, 5.12 Stereochemistry of Molecules with Two or More Asymmetric Carbons, 5.13 Meso Compounds, 5.14 Absolute and Relative Configuration, 5.15 Physical Properties of Diastereomers, 5.16 Resolution of Enantiomers
February 25th
Monday Chapter 4: The Study of Chemical Reactions
4.1 Introduction, 4.2 Chlorination of Methane, 4.3 The Free-Radical Chain Reaction, 4.4 Equilibrium Constants and Free Energy, 4.5 Enthalpy and Entropy, 4.6 Bond-Dissociation Energies, 4.7 Enthalpy Change in Chlorination, 4.8 Kinetics and the Rate Equation, 4.9 Activation Energy and The Temperature Dependence of Rate, 4.10 Transition States, 4.11 Rates of Multistep Reactions, 4.12 Temperature Dependence of Halogenation, 4.13 Halogenation of Higher Alkanes, 4.14 The Hammond Postulate, 4.15 Radical Inhibitors, 4.16 Reactive Intermediates
February 27th
Wednesday Chapter 6: Alkyl Halide: Nucleophilic Substitution and Elimination
6.1 Introduction, 6.2 Nomenclature of Alkyl Halides, 6.3 Common Uses of Alkyl Halides, 6.4 Structure of Alkyl Halides, 6.5 Physical Properties of Alkyl Halides, 6.6 Preparation of Alkyl Halides, 6.7 Reactions of Alkyl Halides: Substitution and Elimination, 6.8 Second-Order Nucleophilic Substitution: The SN2 Reaction, 6.9 Generality of the SN2 Reaction, 6.10 Factors Affecting SN2 Reactions: Strength of the Nucleophile
March
3rd
March
5th
Wednesday Chapter 6: Alkyl Halide: Nucleophilic Substitution and Elimination
6.11 Reactivity of the Substrate in SN2 Reactions, 6.12 Stereochemistry of the SN2 Reaction, 6.13 First-Order Nucleophilic Substitution: The SN1 Reaction, 6.14 Stereochemistry of the SN1 Reaction, 6.15 Rearrangements in SN1 Reactions, 6.16 Comparison of SN1 and SN2 Reactions, 6.17 First-Order Elimination: The E1 Reaction, 6.18 Positional Orientation of Elimination: The Saytzeff Rule, 6.19 Second-Order Elimination: The E2 Reaction, 6.20 Stereochemistry of the E2 Reaction, 6.21 Comparison of E1 and E2 Elimination Mechanisms
March
10th
Monday Chapter 7: Structure and Synthesis of Alkenes
7.1 Introduction, 7.2
The Orbital Description of the Alkene Double Bond, 7.3
Elements of Unsaturation, 7.4
Nomenclature of Alkenes, 7.5
Nomenclature of Cis-trans Isomers, 7.6
Commercial Importance of Alkenes, 7.7
Stability of Alkenes,
7.8 Physical Properties of Alkenes
March
12th
Wednesday Chapter 7: Structure and Synthesis of Alkenes
7.9 Alkene Synthesis by Elimination of Alkyl Halides, 7.10 Alkene Synthesis by Dehydration of Alcohols, 7.11 Alkene Synthesis by High-Temperature Industrial Methods
Learning how to Propose Reaction Mechanisms
March
17th
Monday Chapter 8: Reactions of Alkenes
8.1 Reactivity of the Carbon-Carbon Double Bond, 8.2 Electrophilic Addition to Alkenes, 8.3
Addition of Hydrogen Halides to Alkenes, 8.4 Addition of Water: Hydration of
Alkenes, 8.5 Hydration by Oxymercuration-Demercuration, 8.6 Alkoxymecuration-Demercuration, 8.7
Hydroboration of Alkenes, 8.8
Addition of Halogens to Alkenes
March 19th
Wednesday Chapter 8: Reactions of Alkenes
8.9 Formation of Halohydrins, 8.10
Catalytic Hydrogenation of Alkenes, 8.11
Addition of Carbenes to Alkenes, 8.12
Epoxidation of Alkenes, 8.13
Acid-Catalyzed Opening of Epoxides, 8.14 Syn Hydroxylation to Alkenes, 8.15
Oxidative Cleavage of Alkenes, 8.16 Polymerization of Alkenes
March 24th
Monday ***
No Class ***
March 26th
Wednesday MondayŐs Schedule
Learning About Organic Synthesis
Chapter 9: Alkynes
9.1 Introduction, 9.2 Nomenclature of Alkynes, 9.3 Physical Properties of Alkynes, 9.4 Commercial Importance of Alkynes, 9.5 Electronic Structure of Alkynes, 9.6 Acidity of Alkynes
March 31st
Monday Chapter 9: Alkynes
9.7 Synthesis of Alkynes from Acetylides, 9.8 Synthesis of Alkynes by Elimination Reactions, 9.9 Addition Reactions to Alkynes, 9.10 Oxidation of Alkynes
Learning
how To Design a Multistep Organic Synthesis
April 2nd
Wednesday Chapter 10: Structures and Synthesis of Alcohols
10.1 Introduction, 10.2 Structure and Classification of Alcohols, 10.3 Nomenclature of Alcohols and Phenols, 10.4 Physical Properties of Alcohols, 10.5 Commercially Important Alcohols, 10.6 Acidity of Alcohols and Phenols, 10.7 Synthesis of Alcohols: Introduction and Review, 10.8 Organometallic Reagents for Alcohol Synthesis, 10.9 Addition of Organometallic Reagents to Carbonyl Compounds
April 7th
Monday SECON EXAMINATION (Chapters: 6 – 9)
April 9th
10.9 Addition of Organometallic Reagents to Carbonyl Compounds,
10.10 Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides, 10.11 Reduction of Carbonyl Group: Synthesis of 1ˇand 2ˇ Alcohols, 10.12 Thiols
Monday Chapter 11: Reactions of Alcohols
11.1 Oxidation States of Alcohols and Related Functional Groups, 11.2 Oxidation of Alcohols, 11.3 Additional Methods for Oxidizing Alcohols, 11.4 Biological Oxidation of Alcohols, 11.5 Alcohols as Nucleophiles and Electrophiles; Formation of Tosylates, 11.6 Reduction of Alcohols, 11.7 Reactions of Alcohols with Hydrohalic Acids, 11.8 Reactions of Alcohols with Phosphorus Halides
Wednesday Chapter 11: Reactions of Alcohols
11.9 Reactions of Alcohols with Thionyl Chloride, 11.10 Dehydration Reactions of Alcohols, 11.11 Unique Reactions of Diols, 11.12 Esterification of Alcohols, 11.14 Reactions of Alkoxide
Learning How to Propose Reaction Mechanisms
Learning how to Design a Multistep
Organic Synthesis
Monday Chapter 12: Infrared Spectroscopy and Mass Spectrometry
12.1 Introduction, 12.2 The
Electromagnetic Spectrum, 12.3 The
Infrared Region, 12.4
Molecular Vibrations, 12.5
IR-Active and IR-Inactive Vibrations, 12.6
Measurement of the IR Spectrum, 12.7
Infrared Spectroscopy of Hydrocarbons, 12.8
Characteristics Absorption of Alcohols and Amines, 12.9
Characteristics Absorption of Carbonyl Compounds, 12.10
Characteristic Absorptions of C¾N Bonds
Wednesday Chapter 12: Infrared Spectroscopy and Mass Spectrometry
12.11 Simplified Summary of IR Stretching Frequencies, 12.12 Reading and Interpreting the IR Spectra
12.13 Introduction to Mass Spectrometry, 12.14 Determination of
the Molecular Formula by Mass Spectrometry, 12.15
Fragmentation Patterns in Mass Spectroscopy
Monday Chapter 13: Nuclear Magnetic Resonance Spectroscopy
13.1 Introduction, 13.2 Theory of Nuclear Magnetic Resonance,
13.3 Magnetic Shielding by Electrons, 13.4 The NMR Spectrometer, 13.5 The Chemical Shift, 13.6 The Number of Signals, 13.7 Areas of the Peaks, 13.8 Spin-Spin Splitting, 13.9 Complex Splitting,
13.10 Stereochemical Nonequivalence of Protons
Monday THIRD
EXAMINATION (Chapters: 10 – 13)
Wednesday Catch-up
and Review for Final Examination
Final Examination will be scheduled during the final exam period between Monday the 19th and Saturday the 24th of May of 2008.
ŇI hear, I forget. I see, I remember. I do, I understand.Ó
Chinese proverb