FARMINGDALE STATE COLLEGE DEPARTMENT OF CHEMISTRY. CONTACT HOURS: Lecture: 3 Laboratory: 4

Transcription

1 FARMINGDALE STATE COLLEGE DEPARTMENT OF CHEMISTRY COURSE OUTLINE: COURSE TITLE: Prepared by: Dr. M. DeCastro September 2011 Organic Chemistry II COURSE NUMBER: CHM 271 CREDITS: 5 CONTACT HOURS: Lecture: 3 Laboratory: 4 CATALOG DESCRIPTION: A continuation of CHM 270. Topics covered include: benzene, electrophilic aromatic substitution, arenes, alkyl and aryl halides, alcohols and phenols, ethers and epoxides, carboxylic acids, esters, anhydrides, aldenhydes, ketones, amines, amino acids, carbohydrates, heterocycles, and polymers. PREREQUSITE: CHM 270 IMPORTANT NOTE: ELECTIVE FOR: BOTH THEORY AND LABORATORY PARTS OF THIS COURSE MUST BE TAKEN CONCURRENTLY IN ORDER TO RECEIVE CREDIT. Liberal Arts & Sciences, and Bioscience

2 2 REQUIRED TEXT: LABORATORY MANUAL: Organic Chemistry, 7th edition by Wade, Pearson Publishing Organic Chemistry Laboratory Manual CHM 270 edited by Dr. Michael DeCastro OPTIONAL TEXTS: 1) Contemporary Organic Chemistry by Ternay. 2) Organic Chemistry, by Solomons. 3) Organic Chemistry, by Streitwiesser. 4) Electron Movements, by Weeks. 5) Naming Organic Compounds, by Banks. 6) Organic Organic Chemistry, 1 st Edition, by Fox & Whitesell. 7) Chemistry, by McMurray. REQUIRED SUPPLIES: Laboratory coat and safety glasses.

3 3 FARMINGDALE STATE COLLEGE DEPARTMENT OF CHEMISTRY CHM 271 Organic Chemistry II I. Aromatic Compounds Benzene Lecture Schedule Kekule structure, MO picture, resonance, aromatic character, Huckel s Rule, nomenclature, physical properties, chemical reactions and mechanisms. Section I. - At the end of this section, the student should be able to: 1. Name benzene compounds by IUPAC system. 2. Explain ortho, meta and para substitution. 3. Explain the bonding and stereochemistry of the benzene ring. 4. Explain what creates aromaticity in a ring. 5. Apply Huckel s Rule. 6. Formulate a mechanism of electrophilic aromatic substitution. 7. Predict the products of electrophilic aromatic substitution reactions. 8. Synthesize substituted benzenes. II. Arenes Structure, nomenclature, physical properties and mechanisms. Section II. - At the end of this section, the student should be able to: 1. Draw the general structure of an arene. 2. Name arenes by the IUPAC system. 3. Propose methods of synthesis. 4. Predict the products of reactions of arenes. 5. Explain the importance of reaction conditions on class of product formed. 6. Formulate mechanism of reactions of arenes. 7. Predict directing group influence of arene substitutes.

4 4 III. Alkyl Halides Structure, nomenclature, physical properties, preparations, chemical reactions, Sn 1, Sn 2, E 1, E 2 mechanisms. Section III. - At the end of this section, the student should be able to: 1. Give the structure of an alkyl halide. 2. Name alkyl halides by the IUPAC system. 3. Propose methods of synthesis for alkyl halides. 4. Predict the products of reactions of alkyl halides. 5. Predict the effects of changes in reaction conditions on substitution and elimination reactions. 6. Identify reactions as to type - Sn 1, Sn 2, E 1, or E Formulate mechanisms of reactions of alkyl halides. IV. Aryl Halides Structure, nomenclature, physical properties, preparation, chemical reactions, mechanisms and benzyne intermediate. Section IV. - At the end of this section, the student should be able to: 1. Draw the general structure of an aryl halide. 2. Name aryl halides by IUPAC system. 3. Propose method of synthesis of aryl halides. 4. Predict the products of reaction of aryl halides. 5. Formulate mechanisms of reactions of aryl halides. Unit Exam I- on Units I, II, III, and IV. V. Alcohols Structure, nomenclature, physical properties, preparation, chemical reactions, mechanisms and synthesis. Section V. - At the end of this section, the student should be able to: 1. Give the general structure of an alcohol. 2. Name alcohols by the IUPAC system. 3. Draw structures corresponding to IUPAC names of given alcohols. 4. Predict relative acidities of molecules.

5 5 5. Synthesize alcohols. 6. Predict products of reactions involving alcohols. 7. Formulate the mechanisms of reactions involving alcohols. 8. Explain how the Lucas test is used to distinguish between primary, secondary and tertiary alcohols. 9. Explain the anti-markovnikov s addition of water via hydroboration. VI. Phenols Structure, nomenclature, physical properties, preparation, chemical reactions, mechanisms and synthesis. Section VI. - At the end of this section, the student should be able to: 1. Give the general structure of a phenol. 2. Name substituted phenols. 3. Draw structures for substituted phenols from their names. 4. Predict and explain the directing group influence of the -OH group. 4. Explain the acidity of phenols. 5. Synthesize phenols. 6. Predict products of reactions involving phenols. 7. Formulate mechanisms for reactions involving phenols. VII. Ethers Structure, nomenclature, physical properties, preparation, chemical reactions and mechanisms. Section VII. At the end of this section, the student should be able to: 1. Give the general structure of an ether. 2. Name ethers by the IUPAC system and the common system. 3. Draw structures for ethers from the common or IUPAC name. 4. Explain the unreactivity of these molecules. 5. Synthesize ethers. 6. Predict products of reactions involving ethers. 7. Formulate mechanisms for the formation of ethers.

6 6 8. Explain the directing group influence of the alkoxy and aryloxy groups. VIII. Carboxylic Acids and Derivatives Structures, nomenclature, physical properties, preparation, chemical reactions, mechanisms, acidity, dicarboxylic acids, heteroacids, hydroxy acids, acid halides, acid anhydrides, esters and amides. Section VIII. - At the end of this section, the student should be able to: 1. Give a general structure for a carboxylic acid. 2. Name carboxylic acids by the IUPAC system. 3. Rank compounds in order of increasing acidity. 4. Use electronegativity and resonance arguments to predict the acidity of carboxylic acids. 5. Synthesize aliphatic and aromatic carboxylic acids, acid halides, acid anhyhrides, esters and amides 6. Predict relative reactivity of carboxylic acid derivatives. 7. Predict the product of reactions for carboxylic acids, acid halides, acid anhydrides, esters and amides. 8. Use nucleophilic acyl substitution reactions in synthesis. 9. Formulate mechanisms of nucleophilic acyl substitution reactions. 10. Synthesize compounds via acetoacetic ester and mulonic ester methods. Unit Exam II- on Units V, VI, VII, and VIII. IX. Aldehydes and Ketones Structures, nomenclature, physical properties, preparation, chemical reactions, mechanisms, condensation reactions and synthesis. Section IX. - At the end of this section, the student should be able to: 1. Identify carbonyl containing functional groups.

7 7 2. Give a general structure for an aldehyde and a ketone. 3. Name aldehydes and ketones by the IUPAC system. 4. Draw structures of aldehydes and ketones corresponding to given names. 5. Synthesize aldehydes and ketones. 6. Predict the product of reactions of aldehydes and ketones. 7. Formulate the mechanisms of nucleophilic addition reactions. 8. Compare the relative reactivities of aldehydes and ketones. X. Amines Structure, nomenclature, physical properties, preparation, chemical reactions, mechanisms, synthesis and basicity. Section X. - At the end of this section, the student should be able to: 1. Write a general structure for an amine. 2. Classify amines as primary, secondary, tertiary or quarternary. 3. Name amines by the IUPAC system. 4. Draw structures of amines corresponding to given names. 5. Predict the basicity of amines. 6. Synthesize aliphatic and aromatic amines. 7. Predict the products of reaction of aliphatic and aromatic amines. 8. Use amines in synthetic sequences. XI. Carbohydrates Definition and classifications, aldoses, ketoses, structural determination, cyclic structure, polysaccharides. Section XI. - At the end of this section, the student should be able to: 1. Classify carbohydrates. 2. Identify sugar as D or L.

8 8 3. Draw monosaccharides in the Fischer, Haworth and Chair conformation projections. 4. Predict the products of reactions of monosaccharides. 5. Predict the products of reactions of disaccharides. 6. Deduce the structure of disaccharides. 7. Define the terms monosaccharide, disaccharide, reducing sugar, non-reducing sugar, anomeric center, furanose ring, pyranose ring and glucosides. 8. Explain the Ruff degradation. 9. Explain the Kiliani Fischer method. 10. Explain the mechanism of cyclization reactions. 11. Explain the difference between starch and cellulose. XII. Proteins Amino acids, peptides, classification of proteins, protein structure and Enzymes. Section XII. - At the end of this section, the student should be able to: 1. Identify common amino acids. 2. Draw - amino acids with the correct stereochemistry and in dipolar (zwitterion) form. 3. Draw the structures of simple peptides. 4. Deduce the structure of peptides. 5. Outline the scheme of peptide synthesis. 6. Draw structures of reaction products of amino acids and peptides. 7. Classify proteins as simple, conjugated, fibrous or globular. 8. Explain primary, secondary, tertiary and quarternary structure of proteins. 9. Classify enzymes by structure and function. Unit Exam III- on Units IX, X, XI, and XII.

9 9 FARMINGDALE STATE COLLEGE DEPARTMENT OF CHEMISTRY CHM 271 Organic Chemistry II Text: Introduction to Organic Laboratory Techniques, by Pavia, Lampman & Kriz. LABORATORY SCHEDULE Lab. Period Experiment 1 Extraction of oil of cloves 2 Preparation of Nitrobenzene 3 Preparation of Aniline 4 Preparation of Acetanilide 5-6 Extraction and Purification of a Two Component Mixture 7 Elemental Analysis by Sodium Fusion 8-11 Physical and Chemical Properties of Unknown Formation of Derivatives Identification of the Components of a Mixture by Physical, Chemical and Spectroscopic Means 14 Check Out

10 10 CHM 271 Organic Chemistry II GRADING POLICY Lecture FARMINGDALE STATE COLLEGE DEPARTMENT OF CHEMISTRY There will be 3 exams throughout the course and a final comprehensive exam. The final comprehensive can be used to replace a missed or poor examination grade. Students will be given at least 1 week notice of when the exam will be given. There are no makeup exams and the lowest grade will be dropped. Laboratory The laboratory portion of the course constitutes 30 % of the final grade. There are 13 laboratory experiments in total. The lowest laboratory grade will be dropped. The final laboratory grade will be an average of all laboratory report grades. FINAL GRADE = 70% LECTURE + 30 % LAB GRADE.