Course Descriptions & Syllabi

Course Descriptions & Syllabi

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Areas of Study | | CHEM134 syllabus




COURSE NUMBER: CHEM134
COURSE TITLE:Organic Chemistry II
DIVISION:Sciences
IAI CODE(S): CHM 914
SEMESTER CREDIT HOURS:5
CONTACT HOURS:90
STUDENT ENGAGEMENT HOURS:225
DELIVERY MODE:In-Person

COURSE DESCRIPTION:
This course is the second of a two-semester sequence in Organic Chemistry for students pursuing chemistry, biochemistry, medical or engineering professions. Topics covered include nomenclature, molecular structure, reactivity and synthesis, with some extra emphasis on spectroscopy and applications to biological chemical reactions. Laboratory is required and offers more complex reactions than CHEM133 through the use of more sensitive reagents and multi-step reactions. Lecture meets three hours per week and lab meets four hours per week.

PREREQUISITES:
Completion of Organic Chemistry 1, CHEM133 (IAI: CHM913), the first semester of a year-long course, is required with a grade of a C or better.

NOTES: A lab is required for this course. Some sections will require a separate lab, while other sections will include the lab.

STUDENT LEARNING OUTCOMES:

Students who complete this course should exhibit knowledge and competence in naming of organic compounds, their properties, formation and reactivity through chemical reactions and mechanisms. The student must be able to:

  • Demonstrate knowledge of standard (International Union of Pure and Applied Chemistry, IUPAC) and common nomenclature of organic compounds through the naming of chemical compounds. Classes of compounds discussed in this course include, but are not limited to:
    • Organometallic compounds
    • Alcohols, diols and thiols
    • Ethers
    • Epoxides
    • Sulfides
    • Aldehydes and Ketones
    • Carboxylic acids and their derivatives
    • Enols and Enolates
    • Amines
    • Carbohydrates, lipids, amino acids and nucleic acids
  • Demonstrate comprehension of the properties and reactivity of organic functional groups by ranking them in terms of bonding, nucleophilicity, electrophilicity, leaving groups, etc.
  • Describe the experimental methods and background of basic analytical and spectroscopic techniques.
  • Interpret spectra from basic analytical spectroscopic techniques such as gas chromatography, mass spectrometry, IR spectroscopy, NMR spectroscopy and UV-Visible spectroscopy.
  • Apply their knowledge of basic properties and reactivity of organic functional groups to drawing reaction mechanisms which:
    • Show proper flow of electrons.
    • Predict products for the reaction of unfamiliar compounds.
    • Distinguish between major and minor product formation.
  • Apply their knowledge of chemical reactions and mechanisms to experiments in the laboratory by:
    • Creating appropriate experimental setups with glassware and equipment.
    • Synthesizing compounds in a time-efficient manner.
    • Predicting the products of reactions by drawing the mechanism.
    • Analyzing compound purity using spectroscopic techniques.
    • Summarizing the results and analyzing experimental methods through writing.

TOPICAL OUTLINE:
  • Spectroscopic Methods and Analysis (10%, Week 1-2)
    • NMR spectroscopy
      • Background and uses
      • 1H and 13C spectra interpretation
      • 2D NMR
      • MRI
    • Mass spectrometry
      • Background and uses
      • Spectral interpretation
    • Infrared spectroscopy background and continued interpretation
  • Organometallic Compounds (10%, Week 3-4)
    • Nomenclature
    • Carbon-metal bonds
    • Preparation of organolithium and organomagnesium compounds (Grignard reagents)
    • Synthetic methods using organolithium and organomagnesium compounds
    • Catalysis and metathesis
  • Alcohols, Diols and Thiols (10%, Week 4-5)
    • Nomenclature
    • Preparation of alcohols from aldehydes, ketones, carboxylic acids and epoxides
    • Diol and thiol preparation
    • Alcohol reactions and mechanisms-ether synthesis, esterification, oxidation and biological oxidation
  • Ethers, Epoxides and Sulfides (12%, Week 6-9)
    • Nomenclature, structure and physical properties of ethers, epoxides and sulfides
    • Preparation of ethers, epoxides and sulfides
    • Reactions and mechanisms of ethers-Williamson ether synthesis and acid-catalyzed cleavage
    • Reactions and mechanisms of epoxides-vicinal halohydrins to epoxides, nucleophilic ring opening and acid-catalyzed ring opening
    • Oxidation and alkylation reactions of sulfides
  • Aldehydes and Ketones (13%, Week 9-11)
    • Nomenclature, structure and physical properties of aldehydes and ketones
    • Preparation and sources of aldehydes and ketones
    • Reactions and mechanisms of aldehydes and ketones
      • Hydration
      • Cyanohydrin formation
      • Acetyl formation
      • Primary and secondary amine reactions
      • Wittig Reaction
      • Oxidation
      • Stereoslectivity of reactions
  • Carboxylic Acids and Carboxylic Acid Derivatives (10%, Week 11-12)
    • Nomenclature, structure and physical properties
    • Acidity and acid strength and their effects on reactions
    • Sources and preparation of carboxylic acids
      • Carboxylation of Grignard reagents
      • Hydrolysis of nitriles
    • Nucleophilic acyl substitution and reactions of acyl chlorides to form other carboxylic acid derivations
    • Ester formation and reactions
    • Soponification
  • Enols and Enolates (10%, Week 12-13)
    • Nomenclature and regiochemistry
    • Condensation reactions and mechanisms
      • Aldol and mixed aldol condensation
      • Claisen, mixed Claisen and Dieckmann cyclization
    • Ester synthesis
    • Effects of conjugation of alpha, beta-unsaturated aldehydes and ketones
    • Conjugate addition, Michael and organocopper reactions
  • Amines (5%, Week 13)
    • Nomenclature, structure and physical properties of amines
    • Use of tetraalkylammonium salts for phase-transfer catalysis
    • Preparation of amines through alkylation and reduction reactions
    • Reductive amination
  • Phenols (5%, Week 14)
    • Nomeclature, structure and physical properties of phenols
    • Effects of substituents on phenol properties
    • Naturally occurring phenols and uses of phenols
    • Reactions of phenols-electrophilic aromatic substitution, Kolbe-Schmitt, and oxidation reactions
  • Carbohydrates (5%, Week 14-15)
    • Classes of carbohydrates and nomenclature
    • Structures of carbohydrates-Fischer projections and the D,L notation
    • Reactions of carbohyrates-reduction and oxidation of monosaccharides, periodic acid oxidation, synthesis of oligosaccharides
  • Lipids (5%, Week15)
    • Nomenclature, structure and physical properties of the classes lipids
    • Biosynthesis of lipids and use of enzymes
  • Amino Acids (5%, Week15-16)
    • Classification and stereochemistry of amino acids
    • Preparation of amino acids
    • Biological reactions of amino acids
    • Peptide synthesis and structures (secondary and tertiary)
    • Coenzymes
  • Nucleic Acids (5%, Week 16)
    • Structure and properties of pyrimidines and purines
    • DNA structure and replication
    • Ribonucleic acid structures, properties and biological roles
Weekly Lab Outline - Experiments completed this semester use the techniques from CHEM133 to complete several "Name reactions" and reactions discussed in the lecture portion of the course, as well as successful completion of a multistep reaction. Each lab uses some type of spectroscopy to determine the success of the reaction and product purity. Students are required to discuss their results in written format in a lab report. All labs are conducted in a wet-lab and are hands-on.
Lab Text/Manual Title: CHEM 133 Lab Manual. A.J.(Gaier) Hahne. DACC custom lab manual. Fall 2018 edition.
Activity Title Description of Lab Student Outcome/Skills Delivery Method Activity Time
Lab 1 - Lab Introduction and Safety Orientation

Lecture (due to the shorter safety lab, some of the time is used to lecture, occurs in week 1 only)
Students will review safety information, as well as laboratory policies and procedures.

Completion of the safety orientation is mandatory before a student may participate in any future lab experiments
Locate and discuss proper usage of safety equipment.

List the requirements for proper clothing and footwear in the lab.

List the safety rules for the lab and identify potential violations in a given scenario.

Explain why safety is important in the lab and in their future careers.

*Note: The safety lab must be completed before a student may complete any other experiment.
Hands on 1 hour safety, 1-2 hours lecture
Lab 2 - Spectroscopy Students will interpret spectral data from multiple types of spectroscopy to elucidate chemical structures of unknowns.

Students take IR spectra of the unknowns and interpret these along with Mass Spec and 1H and 13C NMR spectra.
Use an IR to take spectra of solid and liquid samples.

Identify main peaks in IR, Mass Spec, and NMR spectra.

Support determination of an unknown compound using data and basic principles of IR, Mass Spec and NMR.

Analyze experimental results through writing.
Hands on 4 hours
Lab 3 - Grignard Reagents Students will study and perform a Grignard reaction starting from magnesium and bromobenzene to form the initial Grignard reagent, practicing using anhydrous solvents and conditions.

The reaction is heated and stirred in a roundbottom flask equipped with a drying tube.

Students react their Grignard reagent with benzophenone while refluxing in a roundbottom flask, isolate using extractions, purify by removing the byproduct, retrieving with vacuum filtration and characterize their final product using mass and IR spectroscopy.
Create experimental setups using anhydrous reagents and techniques for maintaining dryness.

Draw a mechanism for the reaction.

Reflux a reaction mixture.

Isolate a product using extraction and vacuum filtration.

Calculate percent yield.

Characterize a product using IR spectroscopy.

Support results using data.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 4 - Alcohol Oxidation Students will oxidize a diol with sodium hypochlorite to form a ketone.

The reaction is done while stirring in an ice bath, which is treated with ice and salt.

Product isolation is done through extractions with ether and evaporation of the solvent.

The product is analyzed through mass and IR spectroscopy.
Synthesize a ketone from a diol.

Isolate a product using extraction and solvent evaporation.

Calculate percent yield.

Support results using data.

Characterize a product using IR spectroscopy.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 5 - Aldol Condensation Students will complete a base catalyzed aldol condensation of acetophenone and piperonaldehyde in basic conditions and subsequent dehydration to form an α,β-unsaturated ketone.

The reaction is heated in an Erlenmeyer flask on a hot plate and then the product is crystallized from an aqueous solution.

The crystallized product is isolated through vacuum filtration.

The product is analyzed through mass and IR spectroscopy.
Synthesize an α,β-unsaturated ketone from an aldehyde and a ketone.

Draw a mechanism for the reaction.

Isolate a product using crystallization and vacuum filtration.

Characterize a product using IR spectroscopy.

Support results using data.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 6 - Ester Synthesis Students will prepare an ester via Fischer esterification from an alcohol and carboxylic acid after first using analytical methods to determine the identity of an unknown alcohol and carboxylic acid. The acid catalyzed reaction is refluxed, then extracted with ether and neutralized with base. The product is isolated after evaporating off the solvent. The scent of their ester will determine if their unknown identification was correct. The product is analyzed through mass and IR spectroscopy. Synthesize an ester from an alcohol and a carboxylic acid.

Identify unknown compounds using analytical methods.

Isolate a compound using extractions and solvent evaporation.

Draw a mechanism for the reaction.

Calculate percent yield.

Characterize a product using IR spectroscopy.

Support results using data.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 7 - Friedel Crafts Acylation Students will perform an acid-catalyzed acylation of ferrocene with acetic anhydride. The reaction is refluxed in a roundbottom flask and a condenser. After basic treatment, the product is precipitated and collected with vacuum filtration. The product is analyzed through mass and IR spectroscopy. Complete an acylation reaction.

Isolate a compound using precipitation and vacuum filtration.

Draw a mechanism for the reaction.

Calculate percent yield.

Characterize a product using IR spectroscopy.

Support results using data.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 8 – Michael and Aldol Condensation Reactions Students perform condensation reactions of trans-chalcone and ethyl acetoacetate in basic conditions. The reaction is refluxed in a roundbottom flask equipped with a condenser. The crude product is precipitated, isolated with vacuum filtration and dried in an oven. The product is recrystallized and then analyzed through mass and IR spectroscopy. Complete Michael and Aldol condensation reactions.

Isolate a crude product using precipitation, vacuum filtration and oven drying.

Purify a crude product using crystallization.

Calculate percent yield.

Characterize a product using IR spectroscopy.

Support results using data.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 9 - Selective Reduction to Amines, Week 1 Students will complete and compare two chemoselective reduction reactions on 4-nitroacetanilide to form a carbonyl or amine. Week 1 uses tin as a reducing agent, while heating in a roundbottom flask equipped with a condenser. The crude product is precipitated on treatment with base and removed through vacuum filtration. Students recrystallize to isolate the purified product. Perform a reduction reaction to form an amine group using tin.

Isolate a crude product using precipitation and vacuum filtration.

Purify a crude product using recrystallization.

Calculate percent yield.

Characterize a product using IR spectroscopy.

Support results using data.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 9 - Selective Reduction to Amines, Week 2 Week 2 uses sodium borohydride as the reducing agent. The crude product is extracted using a separatory funnel and crystallized from a concentrated ether solution. The product is isolated using vacuum filtration. The products are analyzed through mass and IR spectroscopy, and then students determine which functional group is formed from which reducing agent. Perform a reduction reaction to form an amine group using sodium borohydride.

Draw a reaction mechanism.

Isolate a crude product using crystallization and vacuum filtration.

Calculate percent yield.

Characterize a product using IR spectroscopy.

Support results using data.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 10 - Aspirin Synthesis Students will complete the synthesis of the analgesic, aspirin, from salicylic acid and acetic anhydride. The reaction is heated in a water bath, and then the crude product is crystallized and filtered out with vacuum filtration. Purification is done by treating with base in aqueous solution and then precipitated upon addition of acid. The purified product is vacuum filtered and analyzed through mass and IR spectroscopy. Synthesize aspirin from salicylic acid and acetic anhydride.

Isolate a product using crystallization, precipitation and vacuum filtration.

Draw a reaction mechanism.

Calculate percent yield.

Characterize a product using IR spectroscopy.

Support results using data.
Hands-on 4 hours
Labs 11-13 - Multistep Synthesis of Nylon-6,6 Students are presented with the idea of using a product as the starting material in another reaction. Enforces the idea of the process of multistep synthesis found in industry.      
Lab 11 - Dehydration of Cyclohexanol The formation of cyclohexene from the dehydration of cyclohexanol in acidic conditions uses simple distillation to push the reaction to completion. After washing with water, the crude product is distilled and characterized by IR. Emphasis is on forming maximum product yield for use of the product in the next reaction. Describe basic principles of an elimination reaction.

Draw a mechanism for an elimination reaction.

Identify the role of each reactant (solvent, nucleophile, electrophile).

Reflux a chemical reaction.

Isolate a product using distillation.

Calculate percent yield.

Characterize a product using IR spectroscopy.

Analyze results through writing.
Hands-on 4 hours
Lab 12 - Synthesis of Adipic Acid Week 2 is the “green” synthesis of adipic acid using a phase transfer catalyst and hydrogen peroxide. The reaction is refluxed in a roundbottom flask with a condenser. The crude product precipitates, is vacuum filtered and then recrystallized from water. Perform a cleavage of a double bond to form a diol.

Describe the role of a phase transfer catalyst.

Draw a reaction mechanism.

Isolate a pure product using precipitation, vacuum filtration, and recrystallization.

Calculate percent yield.

Characterize a product using IR spectroscopy.

Analyze results through writing.
Hands-on 4 hours
Lab 13 - Formation of Nylon Week 3 students reflux the adipic acid with thionyl chloride in a roundbottom flask with a condenser. The reaction is monitored with IR. The product is then reacted with 1,6-diaminohexane in basic conditions to form the polymer, nylon. The product is analyzed through mass and IR spectroscopy. Perform a reaction between a carboxylic acid and an acid chloride.

Perform a polymerization reaction.

Demonstrate the safe usage of acid chlorides.

Monitor a reaction’s progress using IR.

Draw a reaction mechanism.

Calculate percent yield.

Characterize a product using IR spectroscopy.

Reflect on overall success of completing a multistep reaction using percent yield.

Analyze results through writing.
Hands-on 4 hours

TEXTBOOK / SPECIAL MATERIALS:

Text: Organic Chemistry by Francis A. Carey & Robert M. Giuliano, 10th edition. This text will be used daily in class, as well as for homework assignments and general reference.

Lab Manual: CHEM 134 Lab Manual. A.J. Gaier. DACC custom lab manual. Spring 2019 edition. Laboratory Notebook: A bound laboratory notebook with duplicate sheets will be used to record data in lab. The recommended version is the spiral-bound, 100 page carbon copy notebook from Hayden McNeil Publishers.

Safety Goggles: Students must purchase their own laboratory safety goggles and are available in the DACC bookstore. They must be splash goggles with the side protection and NOT safety glasses. Acceptable eyewear will have "Z87" stamped on the side.

Calculator (Optional): Any simple scientific or graphing calculator is sufficient. A calculator may only be necessary for small portions of the class.

Enclosed Shoes & Pants: For lab days. If you are not dressed properly you will not be allowed to participate.


EVALUATION:
Grading is based on a weighted percentage of five different categories with overall grade divisions at 90, 80, 70 and 60 percent. The five categories are:
four or more midterm tests
fifteen lab reports
eight to ten quizzes
classroom work
final exam
40%
20%
10%
10%
20%

Attendance is required and a student may be withdrawn from the class roster due to unexcused absences

Laboratory work must be performed during the regularly scheduled laboratory period. “Make-up” laboratory work at an alternate time will not be an option. No credit will be given for laboratory reports submitted if the student was absent from the laboratory session. If a student has a valid excuse for missing a lecture or a laboratory class, credit for the missed period may be arranged with the instructor and will not be automatically given to the student.


BIBLIOGRAPHY:

STUDENT CONDUCT CODE:
Membership in the DACC community brings both rights and responsibility. As a student at DACC, you are expected to exhibit conduct compatible with the educational mission of the College. Academic dishonesty, including but not limited to, cheating and plagiarism, is not tolerated. A DACC student is also required to abide by the acceptable use policies of copyright and peer-to-peer file sharing. It is the student’s responsibility to become familiar with and adhere to the Student Code of Conduct as contained in the DACC Student Handbook. The Student Handbook is available in the Information Office in Vermilion Hall and online at: https://www.dacc.edu/student-handbook

DISABILITY SERVICES:
Any student who feels s/he may need an accommodation based on the impact of a disability should contact the Testing & Academic Services Center at 217-443-8708 (TTY 217-443-8701) or stop by Cannon Hall Room 103. Please speak with your instructor privately to discuss your specific accommodation needs in this course.

REVISION:
Fall 2019

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