BURLINGTON COUNTY COLLEGE
ORGANIC CHEMISTRY II CHE-242
SYLLABUS 2014/2015
CREDIT HOURS: 3
PREREQUISITE: CHE 240
LECTURER: TERRENCE SHERLOCK
WEBSITES: WWW.CHEMISTRY-SOLUTIONS.COM
OFFICE: TEC 211D
PHONE (856) 222-9311 EXTENSION 2028
EMAIL:
TEXTS: ORGANIC CHEMISTRY 9th EDITION
L. G. WADE, JR.
PRENTICE HALL
Preparing for Your ACS Examination in Organic Chemistry: The Official Guide
IISBN13:978-0970804204
ISBN10:0970804202
Edition/Copyright:98
COURSE DESCRIPTION: This is the second semester of a two-semester organic chemistry course. It is designed for chemistry, biotechnology, biology, engineering, pre-medicine, pre-dental majors and other students wishing to study organic chemistry. The topics covered in the course include: synthesis and reactions of alcohols, ethers, and epoxides. NMR spectroscopy and an introduction to UV spectroscopy are included. Aromatic compounds and their reactions as well as structure and reactions of amines, ketones, aldehydes, carboxylic acids and their derivatives will be discussed in detail. The course will also include investigation into the basic structure and chemistry of carbohydrates, amino acids, proteins, and lipids.
Goals: To introduce the student to:
1. The different types and structures of organic
compounds.
2. The relationship between the structure of an organic compound and its properties.
3. The different types and mechanisms of organic
reactions.
4. Multi-step synthesis in the preparation of organic
compounds.
5. The theory and applications of Nuclear Magnetic Resonance spectroscopy in Organic Chemistry.
6. The basic structure of important biochemical compounds.
INSTRUCTIONAL UNITS:
Unit V - Structure and Reactions of Alcohols, Ethers
and Epoxides. Basic Principles of NMR Spectroscopy.
Unit VI - The Study of Conjugated Systems, Aromaticity
and Reactions of Aromatic Compounds.
Unit VII The Physical and Chemical Properties,
and Reactions of Ketones, Aldehydes,and Amines. Introduction to Carbohydrates and Nucleic Acids.
Unit VIII The Structure, Properties, Reactions and
Mechanisms of Carboxylic Acids and Their
Derivatives. An Introduction to Amino Acids,
Proteins, and Lipids.
ATTENDANCE: Attendance at all lectures is expected and will
be recorded.
TESTS: There will 4 tests given during the semester and the cumulative final exam will be the ACS Organic Chemistry Examination.
Additional Quizzes may be given for purposes of Outcomes Assessment
EVALUATION: Final grade is determined as follows:
ACS Final Exam 40%
Average of tests 60%
Final Grade:
A = 90-100
B+ = 86-89
B = 80-85
C+ = 76-79
C = 70-75
D = 60-69
F = 59 and below
ADVICE:
Organic chemistry is a rigorous course due to the amount of material covered. It is critical that you do not fall behind because it will be very difficult to catch up. One of the most important skills for you to master in the course is to take large amounts of material and organize, categorize, and apply it. Experience has shown that this skill is much more effective than rote memorization.
Be sure to read the relevant sections in the text prior to coming to lecture.
Work problems from the end of chapters and from the Wade website and links contained therein.
Take advantage of my office hours if you need extra help.
Student study groups have proven to be an effective resource.
Good luck and have fun.
rev:TPS 5/28/14
CHE 242 Unit V - The Structure, Synthesis, and Reactions of Alcohols and Ethers. The Theory of Nuclear Magnetic Resonance and interpretation of NMR Spectra.
A. Introduction and Rationale:
Alcohols are a common synthetic reagent due to their versatility. The purpose of this unit is to study the nomenclature, physical and chemical properties, reactions, and synthesis of alcohols and ethers. The second part of the Unit is an introduction into the theory and practice of proton NMR spectroscopy as it relates to determination of structure of organic compounds.
B. Topics:
1. Structure, nomenclature, and classification of alcohols and phenols.
2. Acidity of alcohols and phenols.
3. Synthesis of alcohols.
4. Oxidation and reduction reactions of alcohols.
5. Substitution and dehydration reactions of alcohols.
6. Theory of NMR Spectroscopy.
7. Chemical shift, number of signals, and peak integration.
8. Spin-spin splitting.
9. Interpreting proton NMR spectra.
C. Objectives: The student should be able to:
1. Draw and name alcohols, phenols, diols and thiols.
2. Predict solubilities, boiling points, and acidities of alcohols.
3. Draw resonance structures and use them to predict stability.
4. Predict relative acidities and basicities based on structure, bonding, and resonance of conjugate acid-base pairs.
5. Convert alkenes, alkyl halides, and carbonyl compounds to alcohols.
6. Identify reagents required to interconvert alkanes, alkenes, alcohols, aldehydes, ketones, and carboxylic acids.
7. Use your knowledge to predict mechanisms for new reactions.
8. Use retrosynthetic analysis to propose single and multi-step syntheses of compounds using alcohols as intermediates.
9. Given a structure, determine equivalent protons, number of signals and chemical shift.
10. Determine the numbers of protons in a signal by using the integral trace.
11. Use spin-spin splitting patterns to determine alkyl and other functional groups.
12. Elucidate the structure of unknown compounds by using chemical shifts, integrals, splitting patterns, and IR and/or Mass Spec data.
D. Learning Activities:
1. Always attend all lectures and practice what you have learned by answering end of chapter Study Problems.
2. Read Chapter Ten in Wade Text.
3. Review Chapter Ten material on Wade website:
4. Read Chapter Eleven in Wade Text.
5. Review Chapter Eleven material on Wade website:
6. Read Chapter Thirteen in Wade Text.
7. Review Chapter Thirteen material on Wade website:
8. Read Chapter Fourteen in Wade text.
9. Review Chapter Fourteen material on Wade website:
REVISION 8/1/14 TPS
CHE 242 Unit VI – Conjugated Systems and Ultraviolet Spectroscopy. Aromaticity and Reactions of Aromatic Compounds.
A. Introduction and Rationale:
The first part of this Unit will focus on the unique properties of compounds containing conjugated double bonds. A brief introduction to ultraviolet spectroscopy will be included as a method to determine structures. Aromatic compounds and their reactions comprise the second part of the Unit.
B. Topics:
1. Structure and stability of conjugated dienes.
2. 1,2 and 1,4 addition to conjugated dienes, kinetic versus thermodynamic control.
3. Diels-alder reactions.
4. Ultraviolet absorption spectroscopy.
5. The structure and properties of benzene.
6. Huckel’s rule, aromatic, antiaromatic, and non-aromatic compounds.
7. Nomenclature, properties and spectroscopy of benzene derivatives.
8. Electrophilic aromatic substitution, nitration, sulfonation, and halogenation.
9. The directing effects of substituent groups on EAS reactions.
10. The activating/deactivating effects of substituent groups on EAS reactions.
11. Friedel-Crafts alkylation and acylation reactions
12. Side chain reactions of benzene derivatives
13. Reactions of phenols.
C. Objectives: The student should be able to:
1. Show resonance structures of conjugated dienes.
2. Explain thermodynamic vs. kinetic control in addition reactions of conjugated dienes.
3. Explain basic UV spectroscopy theory, use Beers Law, and interpret UV spectra.
4. Use Huckel’s rule to whether a given compound will be aromatic, antiaromatic, or nonaromatic.
5. Name aromatic compounds and draw their structures from the names.
6. Use NMR, IR, and UV spectra to determine aromatic structures. Given an aromatic compound, predict the important spectral features.
7. Predict products and show mechanisms for the common EAS reactions.
8. Draw resonance structures for complexes resulting from electrophilic attack on substituted aromatic rings.
9. Explain which substituents are activating and which are deactivating, and show why they are ortho/para-directing or meta-directing.
10. Design syntheses that use the influence of substituents to generate the correct isomers of multisubstituted aromatic compounds.
11. Predict the product of EAS reactions on molecules containing substituents on one or more aromatic rings.
12. Explain how the reactions of side chains are affected by the presence of the aromatic ring, and use these reactions in syntheses.
13. Explain the acidity of phenols.
14. Predict the products of oxidation and substitution of phenols, and use these reactions in syntheses.
D. Learning Activities:
1. Always attend all lectures and practice what you have learned by answering end of chapter Study Problems.
2. Read Chapter Fifteen in Wade Text.
3. Review Chapter Fifteen on Wade website:
4. Read Chapter Sixteen in Wade Text.
5. Review Chapter Sixteen material on Wade website:
6. Read Chapter Seventeen Sections
7. Review Chapter Seventeen on Wade website:
REVISION 8/1/14 TPS
CHE 242 Unit VII – Ketones, Aldehydes, Amines, Carbohydrates and Nucleic Acids.
A. Introduction and Rationale:
The topics in this unit are central importance to chemistry, biochemistry. Naturally occurring and synthetic compounds will be discussed. Many amines are used as drugs and medicines due to their biological activity. An introduction to the structure, and classification of carbohydrates and the structure of DNA is included in the second part of the Unit.
B. Topics:
1. Structure, nomenclature, and physical properties of ketones and aldehydes.
2. Infrared and Proton NMR spectroscopy of aldehydes and ketones.
3. Synthesis of ketones and aldehydes.
4. Mechanism of Nucleophilic addition.
5. Reactions of ketones and aldehydes.
6. Structure, nomenclature and physical properties of amines.
7. Basicity of amines.
8. Infrared and Proton NMR spectroscopy of amines.
9. Reactions of amines
10. Classification of carbohydrates.
11. Cyclic structures of monosaccharides.
12. Disaccharides and polysaccharides
13. Introduction to nucleic acids.
14. The structure of deoxyribonucleic acid.
C. Objectives: The student should be able to:
1. Name ketones and aldehydes, and draw structures from their names.
2. Interpret NMR, IR, and mass spectra of ketones and aldehydes, and use spectral information to determine structure.
3. Propose effective single and multistep syntheses of aldehydes and ketones.
4. Predict the products of ketones and aldehydes when reacted with common reagents.
5. Show how ketones and aldehydes can be converted in to other functional groups
6. Use retrosynthetic analysis to propose effective multistep syntheses using ketones and aldehydes as intermediates and protecting the carbonyl group if necessary.
7. Name amines and draw structures from their names
8. Interpret NMR, IR, and mass spectra of amines, and use spectral information to determine structure
9. Explain how the basicity of amines varies with structure, hybridization, and Aromaticity.
10. Predict the products of amines when reacted with common reagents.
11. Use arenediazonium salts in diazo coupling reactions.
12. Show how to synthesize amines from other amines, ketones, aldehydes, acid chlorides, nitro compounds, alkyl halides, nitriles, and amides.
13. Use retrosynthetic analysis to propose effective multistep syntheses using amines as intermediates and protecting the amine group if necessary.
14. Draw the Fisher projection of glucose and the chair conformation of both anomers of glucose from memory.
15. Recognize the common types of glycosidic linkages in disaccharides and polysaccharides.
16. Differentiate the structures of DNA and RNA.
D. Learning Activities:
1. Always attend all lectures and practice what you have learned by answering end of chapter Study Problems.
2. Read Chapter Eighteen in Wade Text.
3. Review Chapter Eighteen material on Wade website:
4. Read Chapter Nineteen in Wade Text.
5. Review Chapter Nineteen material on Wade website:
6. Read Chapter Twenty-Three in Wade Text.
7. Review Chapter Twenty-Three material on Wade website:
REVISION 8/1/14 TPS
CHE 242 Unit VIII –Carboxylic Acids and Derivatives, and an Introduction to Amino Acids, Peptides, Proteins, and Lipids.
A. Introduction and Rationale:
The topics in this unit are also of central importance to industrial chemistry, and biochemistry. Derivatives of carboxylic acids are important precursors to synthetic polymers. Naturally occurring esters, and lactams are important compounds in the flavoring and pharmaceutical industries. The nature of amino acids and proteins will be introduced. The final part of the Unit is comprised of an introduction to lipids such as fats, oils, waxes, triglycerides, and steroids.
B. Topics:
1. Structure, nomenclature, and physical properties of carboxylic acids.
2. Acidity of carboxylic acids.
3. Spectroscopy of carboxylic acids.
4. Synthesis, key reactions, and reaction mechanisms of carboxylic acids.
5. Structure, nomenclature, and physical properties of carboxylic acid derivatives.
6. Spectroscopy of carboxylic acids
7. Interconversion of derivatives via Nucleophilic acyl substitution.
8. Structure and stereochemistry of alpha amino acids.
9. Classification, levels of protein structure.
10. Structure of Fats, Oils, Triglycerides, Waxes, and Steroids.
11. Structure-Property Relationships of #10 (above).
12. Soaps vs. Detergents Properties and Structure.
C. Objectives: The student should be able to:
1. Name carboxylic acids, and draw structures from their names.
2. Show how acidity varies with substitution.
3. Interpret NMR, IR, and mass spectra of carboxylic acids, and use spectral information to determine structure.
4. Show how to synthesize carboxylic acids from oxidation reactions of aldehydes and alcohols, carboxylation of Grignard reagents, hydrolysis of nitriles, and oxidation of alkylbenzenes.
5. Predict the products of carboxylic acids when reacted with common reagents.
6. Show how carboxylic acids are amides and esters using acid chlorides as intermediates. Propose mechanisms for these nucleophilic substitutions.
7. Name carboxylic acids, and draw structures from their names
8. Compare physical properties of acid derivatives.
9. Interpret spectra of carboxylic acids, and use spectral information to determine structure. Show how carbonyl-stretching frequency in IR spectrum can be used to identify the type of acid derivative.
10. Show how acid derivatives are interconverted using Nucleophilic substitution from more reactive to less reactive derivatives.
11. Propose a mechanism for the acid or base catalyzed hydrolysis reactions of derivatives.
12. Show what reagents are used for the reduction of derivatives and what the products of the reduction reactions are.
13. Show what products result from the addition of Grignard and other organometallic reagents to acid derivatives.
14. Use perspective drawings and Fisher projections to show chemistry of D and L amino acids.
15. Discuss and identify the four levels of protein structure.
16. Classify lipids based on structure and physical properties.