Title of Course Organic Chemistry II ... Instructor: Carlos Alva ... Study Guide and
Solutions Manual for McMurry Organic Chemistry 6th Ed., by Susan McMurry,.
BOROUGH OF MANHATTAN COMMUNITY COLLEGE City University of New York Department of Science
Title of Course Organic Chemistry II CHE 240 Section 521 Credits: 5
Class hours: 3 Lab hours: 4 Instructor: Carlos Alva Phone: (212) 220-1319 Office: N-659 E-mail:
[email protected]
Course Description This two-semester course sequence is the study of the structure and properties of the fundamental classes of organic compounds with emphasis on reactivity, reaction mechanism, stereochemistry, electronic theory and applications to allied fields. Prerequisites/Co-requisites MAT 056, CHE 201/202 and CHE 230. Student Learning Outcomes Students will be able to discuss and show proficiency in topics related to: Structure determination using Infrared and Proton Nuclear Magnetic Resonance Spectroscopy. Conjugated dienes and their reactivity, the Diels-Alder reaction. Benzene, Aromaticity, and Hückel’s 4 n + 2 and 4 n rules. Chemistry of Benzene: electrophilic and nucleophilic aromatic substitution reactions such as Friedel-Crafts alkylation/acylation, aromatic halogenation, nitration, sulfonation, etc. Structure, reactivity, reactions and synthesis of alcohols, phenols, ethers, and epoxides. Structure, reactivity, reactions and synthesis of carbonyl containing compounds such as aldehydes, ketones, carboxylic acids, esters, anhydrides, and amides. Nucleophilic addition reactions of aldehydes and ketones. Carbonyl alpha-substitution reactions. Organic transformations of carboxylic acids and nitriles. Synthetic organic techniques for the building of small and large molecules and to show their relationship with biological structures. Organic laboratory techniques and skills to synthesize, separate, purify and characterize (by chemical and spectroscopic techniques) organic compounds. Use of Technology This student-centered course is taught with computers and is writing-intensive. It is essential that each student participate in all classroom activities. The latter include interactive computer-based tutorials, case studies and writing exercises; these are designed to facilitate active learning. In the laboratory, the students will become familiarized with the preparation and analysis of organic compounds using an Infrared Spectrophotometer and a Fourier-transform 60 MHz Proton and Carbon Nuclear Magnetic Resonance instrument.
Required Texts 1. Organic Chemistry by John McMurry, Brooks-Cole Publishing Company, 6th Ed., 2004. Note: the textbook is accompanied by an Organic Chemistry Models Kit. 2. Organic Laboratory Techniques: small-scale approach, by D.L. Pavia, G.M. Lampman, G.S. Kriz, and R.G. Engel, Saunders College Publishing, 1st Ed., 1998. Required Lab gear 1. Safety goggles (can be borrowed from college) 2. Lab coats or aprons
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Recommended Additional Books 1. Study Guide and Solutions Manual for McMurry Organic Chemistry 6th Ed., by Susan McMurry, Houghton Mifflin Company, 6th Ed. 2. Laboratory notebook
Evaluation & Requirements of Students Each semester there will be a minimum of three examinations, a comprehensive final examination, and fulfillment of laboratory requirement. The average of your lecture exams and final exam grades must be greater than 60% to permit a passing grade, regardless of your laboratory grade. The laboratory will be evaluated in preparation, work, and report. A student who is absent from more than one laboratory session seriously jeopardizes his/her grade for the course. The students are encouraged to work as many problems found at the end of the chapter until the main content of the chapter is mastered. The use of the molecular models is recommended to visualize the stereochemistry and the three-dimensional aspect of the organic compounds. The Study Guide and Solutions Manual is useful for checking your answers. Outline of Topics Chapter
Lecture Topics
12 12.5 to 12.9
Structure Determination: Infrared Spectroscopy. Spectroscopy and the Electromagnetic Spectrum. Infrared Spectroscopy of Organic Molecules. Interpreting Infrared Spectra. Infrared Spectra of Hydrocarbons. Infrared Spectra of Some Common Functional Groups.
13 13.1 to 13.3 13.8 to 13.13
Structure Determination: Nuclear Magnetic Resonance Spectroscopy. Nuclear Magnetic Resonance Spectroscopy. The Nature of NMR Absorptions. Chemical Shifts. 1 H NMR Spectroscopy and Proton Equivalence. Chemical Shifts in 1H NMR Spectroscopy. Integration of 1H NMR Absorptions. Spin-Spin Splitting. Uses of 1H NMR Spectroscopy.
14 14.1 to 14.6
Conjugated Dienes. Preparation and Stability of Conjugated Dienes. Molecular Orbital description of 1,3Butadiene. Electrophilic Additions to Conjugated Dienes: Allylic Carbocations. Kinetic versus Thermodynamic Control of Reactions. The Diels-Alder Cycloaddition Reaction. Characteristics of the Diels-Alder Reaction.
15 15.1 to 15.10
Benzene and Aromaticity. Sources of Aromatic Hydrocarbons. Naming Aromatic Compounds. Structure, Stability and Molecular Orbital Description of Benzene. Aromaticity and the Hückel 4n + 2 Rule. Aromatic Ions. Pyridine and Pyrrole. Why 4n + 2 ? Polycyclic Aromatic Compounds: Naphthalene. Spectroscopy of Aromatic Compounds
16 16.1 to 16.12
Chemistry of Benzene: Electrophilic Aromatic Substitution. Bromination of Aromatic Rings. Other Aromatic Substitutions. Alkylation of Aromatic Rings: The Friedel-crafts Reaction. Acylation of Aromatic Rings. Substituent Effects in Substituted Aromatic Rings. An Explanation of Substituent Effects. Trisubstituted Benzenes: Additivity of Effects. Nucleophilic Aromatic Substitution. Benzyne. Oxidation and reduction of Aromatic Compounds. Synthesis of Trisubstituted Benzenes.
17 17.1 to 17.12
Alcohols and Phenols. Naming Alcohols and Phenols. Properties of Alcohols and Phenols: Hydrogen Bonding, Acidity and Basicity. Preparation of Alcohols: a Review. Alcohols from Reduction of Carbonyl Compounds. Alcohols from reaction of Carbonyl Compounds with Grignard Reagents. Some Reactions of Alcohols. Oxidation of Alcohols, Protection of Alcohols Preparation and Uses of Phenols. Reactions of Phenols. Spectroscopy of Alcohols and Phenols.
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18 18.1 to 18.9, 18.11
Ethers, Epoxides, and Sulfides. Naming Ethers. Structure, Properties, Names, and Sources of Ethers. The Williamson Ether Synthesis. Alkoxymercuration of Alkenes. Reaction of Ethers: Acidic Cleavage. Reaction of Ethers: Claisen Rearrangement. Cyclic Ethers: Epoxides. Ring-opening Reaction of Epoxides. Crown Ethers. Spectroscopy of Ethers.
19 19.1 to 19.12, 19.14, 19.16
Aldehydes and Ketones: Nucleophilic Addition Reactions. Naming Aldehydes and Ketones. Preparation of Aldehydes and Ketones. Nucleophilic Addition Reactions of Aldehydes and Ketones. Relative Reactivity of Aldehydes and Ketones. Nucleophilic Addition of Water: Hydration. Nucleophilic Addition of HCN: Cyanohydrin Formation. Nucleophilic Addition of Grignard Reagents and Hydride Reagents: Alcohol Formation. Nucleophilic Addition of Amines: Imine and Enamine Formation. Nucleophilic Addition of Hydrazine: the Wolff-Kishner Reaction. Nucleophilic Addition of Alcohols: Acetal Formation. Nucleophilic Addition of Phosphorus Ylides: the Wittig Reaction. Conjugate Nucleophilic Addition to α,β-unsaturated Aldehydes and Ketones. Spectroscopy of Aldehydes and Ketones.
20 20.1 to 20.10
Carboxylic Acids and Nitriles. Naming Carboxylic Acids and Nitriles. Structure and Physical Properties of Carboxylic Acids. Dissociation of Carboxylic Acids. Substituent Effects on Acidity. Substituent Effects in Substituted Benzoic Acids. Preparation of Carboxylic Acids. Reaction of Carboxylic Acids: An Overview. Reduction of Carboxylic Acids. Chemistry of Nitriles. Spectroscopy of Carboxylic Acids.
21 21.2 to 21.7, 21.10
Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions. Nucleophilic Acyl Substitution Reactions. Nucleophilic Acyl Substitution Reactions of Carboxylic Acids. Chemistry of Acid Halides. Chemistry of Acid Anhydrides. Chemistry of Esters. Chemistry of Amides. Spectroscopy of Carboxylic Acid Derivatives.
22 22.1 to 22.3, 22.5 to 22.7
Carbonyl Alpha-Substitution Reactions Keto-Enol Tautomerism. Reactivity of Enols: The mechanism of Alpha-Substitution Reactions. Alpha Halogenation of Aldehydes and Ketones. Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation. Reactivity of Enolate Ions. Halogenation of Enolate Ions: The Haloform Reaction.
Week
Experiments For Organic Chemistry 2
1 2 3 4 5 6 7 8 9 10 11 12 13/14
Safety Video. Check-in. Infrared Spectroscopy analysis of selected compounds. NMR Spectroscopy analysis of selected compounds. Synthesis of N-phenylmaleimide, a dienophile in Diels-Alder reactions. Diels-Alder reaction between N-phenylmaleimide and furan. Separation, purification, and analysis of exo/endo products from a Diels-Alder reaction. Nitration of Methylbenzoate. Synthesis of acetaminophen: acetylation of p-aminophenol. Qualitative Analysis of Alcohols. Qualitative Analysis of Aldehydes and Ketones Classification tests Aldol reaction Analysis of an Unknown Liquid and Solid
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