Course Descriptions & Syllabi

Course Descriptions & Syllabi

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Areas of Study | | CHEM133 syllabus




COURSE NUMBER: CHEM133
COURSE TITLE:Organic Chemistry I
DIVISION:Sciences
IAI CODE(S): CHM 913
SEMESTER CREDIT HOURS:5
CONTACT HOURS:90
STUDENT ENGAGEMENT HOURS:225
DELIVERY MODE:In-Person

COURSE DESCRIPTION:
This course is the first semester of a two-semester sequence in Organic Chemistry for students pursuing chemistry, biochemistry, medical or engineering professions. Topics covered are meant to build basic skills and knowledge in nomenclature, functional groups, molecular structure and analysis, reactivity and synthesis. Laboratory is required and covers the general techniques needed in organic synthesis and spectroscopic analysis methods. The lecture meets three hours per week and the lab is four hours per week.

PREREQUISITES:
CHEM102

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:
    • Alkanes and cycloalkanes
    • Alcohols
    • Alkyl halides
    • Alkenes
    • Alkadienes and allylic systems
    • Arenes
  • 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 and spectroscopic techniques such as Thin Layer Chromatography, melting and boiling point determination, gas chromatography, IR and UV-Visible spectroscopy.
  • Apply 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 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:
  • Chemical Bonding (Weeks 1-2)
    • Introduction to organic chemistry and its compounds
    • Major function groups
    • Naming - common and IUPAC systematic
    • Physical properties (such as intermolecular forces, melting point and boiling point) and their relation to solubility and structure
    • Polarity of molecules and dipole moments
    • Bonding in organic compound - covalent and ionic
    • Hybridization - sp3, sp2 and sp
    • Acid-base theories - Arrhenius, Bronsted-Lowry and Lewis
    • Resonance
    • Formal charge and oxidation state
    • Structural formulas
  • Alkanes (Week 2-3)
    • Classes of hydrocarbons and functionally substituted derivatives of alkanes
    • Constitutional isomers and nomenclature
    • Physical properties of hydrocarbons
    • Formation, chemical reactions and thermochemistry of hydrocarbons
  • Conformations of Alkanes and Cycloalkanes (Week 3-4)
    • Conformational analysis as depicted by the commonly used representations
    • Chair and boat conformations of cyclohexane
    • Heterocyclic compounds and their properties
  • Stereochemistry (Week 5)
    • Enantiomers and chiral molecules
    • Specific rotation and polarimetry
    • R and S configurations
    • Conformational and configurational isomerism
    • Rate of mutarotation of glucose
    • Reactions which form stereogenic centers
    • Chiral molecules with multiple stereogenic centers
  • Alcohols and Alkylhalides (Week 6)
    • Nomenclature and structure (primary, secondary and tertiary alcohols)
    • Solubility and hydrogen bonding
    • Bronsted acid-base theory and pK values
    • Proton transfer theory
    • Reactions and mechanisms of alcohols and alkyl halides (SN1 & SN2)
    • Heats of reaction
  • Nucleophilic Substitution (Week 7)
    • Relative reactivity of leaving groups and nucleophiles
    • SN2 and SN1 reactions and their mechanisms and stereochemistry
    • Effects of structure and solvent polarity on reaction rates
    • Substitution reactions and their corresponding competitive elimination reactions
  • Alkenes: Elimination and Addition Reactions (Week 9-10)
    • Nomenclature, structure and physical properties
    • Dehydration of alcohols and Zaitsev's Rule
    • Dehydrohaligenation of alkylhalides
    • Mechanism and stereochemistry elimination and addition
    • Electrophilic addition and Markovnikov's Rule
    • Free radical addition: Anti-Markovnikov orientation
    • Hydroboration-oxidation, halohydrin formation and ozonolysis
  • Radical Reactions (Week 12)
    • Homolytic cleavage
    • Structure, stability and bonding of radicals
    • Radical Reactions
      • Radicals in mechanisms
      • Halogenation of Alkanes
      • Free radical addition of Hydrogen
      • Metal-Ammonia reduction
      • Polymerization
  • Alkynes (Week 13)
    • Structure, formation and nomenclature
    • Relative acidity of acetylene
    • Alkylation, elimination and addition reactions
  • Dienes (Week 14)
    • Allylcations and free radicals and their reactions
    • Conjugation and electron delocalization
    • 1,2- versus 1,4-addition reactions
    • Diels-Alder reaction
    • Molecular orbitals of polyenes
  • Arenes and Aromaticity (Week 15-16)
    • Benzene
      • Structure and resonance stability
      • Nomenclature of benzene and its derivatives
      • Aromaticity and Hückel's Rule
    • Reactions
      • Electrophilic aromatic substitution
      • Directing effects of substituent groups
      • Mechanism of substitution and the benzenonium ion
      • Inductive and resonance effects on orientation
      • Substitution on ring verses side chain for arenes
  • Spectroscopy (Covered in lab--see experiments below)
    • Background and methods for use of gas chromatography, ultraviolet and infrared spectroscopy
    • Use of gas chromatography, ultraviolet and infrared spectroscopy in the lab section for product analysis and purity assessment

Weekly Lab Outline - Experiments completed in this semester teach basic techniques for synthesis and analysis. Spectroscopy is used where applicable to determine the success of the reaction and product purity. Students are required to discuss their results in written format. 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 hour lecture
Lab 2 - Melting Point & Boiling Point Students take the melting and boiling points of known and unknown solids and liquids using micro- and ultramicroscale techniques. Demonstrate usage of a Mel-Temp apparatus for melting and boiling point determination.

Describe melting point range and boiling point.

Identify an unknown compound using melting and boiling point determination.

Explain deviations in melting or boiling point data using basic principles of these techniques.

Support determination of an unknown compound using data and basic principles of melting and boiling point determination.

Analyze experimental results through writing.
Hands on 4 hours
Lab 3 - Recrystallization Purify an unknown sample containing impurities based on simple recrystallization techniques. The purified product is removed via vacuum filtration. Students characterize purified product based on melting points. Purify an unknown sample containing impurities using recrystallization.

Identify an unknown using melting point determination.

Support compound identification using data and basic principles of melting points and recrystallization.

Calculate percent recovery.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 4 - Separation by Extraction Separate a mixture of water soluble and organic soluble components through extraction using a separatory funnel.

The mixture components are isolated, their identities determined through melting point and a percent recovery is calculated.
Separate a mixture of water soluble and organic soluble components through extraction.

Isolate solids using precipitation, filtration and evaporation of solvent.

Describe the polarity of solvents and solutes.

Determine the identity of an unknown compound using melting point determination.

Support compound identification using data and basic principles of melting points, polarity and extraction.

Calculate percent recovery.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 5 - Thin Layer Chromatography Examine the relative polarities of compounds using thin layer chromatography.

Students determine the ideal solvent to separate aspirin, caffeine, acetaminophen and an over-the-counter analgesic containing a mixture of these three compounds.

Rf values are calculated and UV light is used to image the TLC plates.
Rank compounds from least to most polar.

Load dissolved solid samples onto TLC plates.

Identify the optimal solvent system for a set of compounds using TLC.

Calculate Rf values.

Identify components in a mixture using Rf values.

Support compound identification using data and basic principles of TLC and polarity.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 6 - Column Chromatography Isolate different components of an analgesic tablet with basic flash chromatography.

TLC is used to monitor the column progress.

The isolated compounds are compared to the pure form and massed to determine the recovery.
Load a column using dry-pack or slurry method.

Run a sample on a column.

Identify components in a fraction using TLC.

Isolate solids from fractions by evaporating excess solvents.

Identify components in a mixture using Rf values.

Support compound identification using data and basic principles of column chromatography and polarity.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 7 - Infrared (IR) Spectroscopy Determine the identity of unknown compounds through infrared spectroscopic analysis.

Students take the IR of two liquids and two solids and interpret their spectra to determine their identity.
Determine the identity of unknown compounds through infrared spectroscopic analysis.

Use an IR to take the spectra of solid and liquid samples.

Identify functional groups on IR spectra.

Use IR spectra analyses to support identification of an unknown compound.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 8 - Isolation of Caffeine from Tea (Part I) Extract caffeine from a sample of tea leaves and isolate the crude material.

Students isolate the crude caffeine using a salt solution, filtration through diatomaceous earth, and then through the evaporation of solvent to the crude product.
Use basic extraction techniques to isolate crude caffeine from tea leaves.

Operate a vacuum filtration setup.

Describe basis for isolation techniques using knowledge of structure and polarity.

Analyze experimental results through writing.
Hands-on 4 hours
Lab 9 - Isolation of Caffeine from Tea (Part II) Purify crude caffeine by sublimation done in a petri dish on a hot plate with a beaker of ice water.

Students perform an extraction with pure caffeine to calculate the partition coefficient which allows them to calculate a percent recovery.
Purify a crude product using sublimation.

Describe the basic principles of sublimation.

Explain the theory behind a partition coefficient.

Calculate a partition coefficient from extraction of compound from a solution.

Calculate percent recovery using experimental yield and the partition coefficient.

Analyze experimental results through writing.
Hands-on 4 hours
Labs 10 & 11 - Distillation & Gas Chromatography Distill a mixture of organic liquids and analyze the distillate with gas chromatography.

Students use simple distillation using a roundbottom flask, multipurpose adapter and condenser in week 1 and fractional distillation using the addition of a fractionating column to the simple distillation glassware setup in week 2 of the experiment.

The fractions from the distillations are analyzed by Gas Chromatography, and the results two distillation techniques are compared.
Isolate components of a liquid mixture using simple and fractional distillation.

Describe the theory behind gas chromatography.

Run a sample on the GC.

Compare retention times on a chromatograph.

Explain experimental results using data and theory of distillation and GC.

Analyze results through writing.
Hands-on 8 hours
Lab 12 - SN1 Substitution Examine the SN1 mechanism and rate of reaction.

Students react 2-butanol with ammonium bromide in acidic conditions under reflux.

The crude product is distilled with simple distillation to isolate the substitution product and characterize it through percent yield and IR spectroscopy.
Describe basic principles of an SN1 reaction.

Draw a mechanism for an SN1 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 13 - SN1 Substitution Examine the SN2 mechanism and rate of reaction.

Students react sodium acetate and n-butyl bromide under reflux, isolate the product using simple distillation and characterize the product through percent yield and IR spectroscopy.
Describe basic principles of an SN2 reaction.

Draw a mechanism for an SN2 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 14 - Dehydration of Cyclohexanol Examine a simple elimination reaction of an alcohol to an alkene.

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.
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 15 - Nucleophilic Aromatic Substitution Students will explore the activating and deactivating effects of a disubstituted benzene on nucleophilic substitution.

Students react 2-bromo-1,4-dinitrobenzene in toluene with tetrabutylammonium bromide in an aqueous solution of potassium thiocyanate.

The crude product is extracted with water and then recrystallized from chloroform.

The purified product is vacuum filtered from solution and characterized with percent yield and IR spectroscopy.
Describe basic principles of a nucleophilic aromatic substitution reaction.

Draw a mechanism for an a nucleophilic aromatic substitution reaction.

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

Isolate a product using extraction and recrystallization.

Calculate percent yield.

Characterize a product using IR spectroscopy.

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 133 Lab Manual. A.J. (Gaier) Hahne. DACC custom lab manual. Fall 2018 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
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.

Notes:
All students must pass the laboratory portion of the class in order to pass the course.

The final exam will include all material covered in the semester. Every student is required to take the final exam at the scheduled time. Each student must take and pass the cumulative final in order to pass the course.

A curve may be applied at the instructor's discretion.


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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