Syllabus • Spring 2020

Click here for a PDF version of the syllabus.

I. Course Information

Course
Prefix Number CRN Name Credit Hours Lecture Hours Lab Hours
CHM 224-001 10035 Organic Chemistry II 5 3 6

Class Schedule
Instructor/CRN Type Time Days Location
Landrie
10035		 Lecture 11:00 am - 12:15 am TR Lee Center 156
Lab 12:30 am - 3:20 pm TR Lee Center 340

Instructor

 Dr. Chad L. Landrie
Chair of Physical Sciences
Professor of Chemistry
Office Room: 109 Lee Center
Office Phone: (847) 376-7439
Email: clandrie@oakton.edu
Email: chadlandrie@gmail.com
URL: http://oakton.chadlandrie.com
Chemical Inventory: http://stockroom.chadlandrie.com
Blog: http://chadlandrie.blogspot.com
Twitter: @chadlandrie
YouTube: http://www.youtube.com/user/chadlandrie

Students may also contact me through a variety of IM clients listed in the table below, particularly during office hours. For Dr. L’s complete semester schedule, visit the Calendar page.

Instant Messaging Dr. L's User ID Client Link/Info
Google Talk chadlandrie@gmail.com www.google.com/talk
Skype clandrie www.skype.com

Office Hours
Day Time Location
MWF 11:00 am - 2:00 pm 109 Lee SHC
TR 3:30 pm - 5:30 pm 340 or 109 Lee SHC


Students who cannot attend during the above times may send me and email to request an appointment or by going to http://chadlandrie.youcanbook.me/. Although I will guarantee my availability during the above hours, I am also available at other times when I am not teaching for walk-ins.

Required & Recommended Resources
1. Required McMurray, J. Organic Chemistry, 9th ed.; Cengage: Boston, MA, 2016.  ISBN: 978-1-305-08048-5 or McMurray, J Organic Chemistry Loose Leaf with OWL, 9th ed., 2016.   ISBN: 978-1-305-70102-1.
2. Required: OWLv2. This is the Cengage online homework platform. An access code is bundled with the loose-leaf text sold by the Oakton Bookstore. It can also be purchased directly from Cengage. Follow instructions within D2L. Access code required after 14-day trial period..
3. Required: CHM 221/223 – Organic Chemistry I Laboratory Experiments.
4. Required: Student Lab Notebook, Hayden-McNeil, ISBN: 978-1-930882-74-4 (Or similar; Must be spiral-bound and contain at least 50 pages.)
5. Required: Chemical splash goggles (indirectly vented). The goggles must seal completely around the face. Shield-type or glasses-type are not allowed.
6. Recommended: i>Clicker (1 or 2); MacMillan (www.iclicker.com); ISBN: 1429280476. If students do not wish to purchase their own i>Clicker, one will be provided to them at the beginning of each class.
7. Recommended: Molecular model set. Molecular model set. Preferred set is “MOLECULAR VISIONS Organic, Inorganic, Organometallic” in a green plastic box. Sold by Darling Models, INC. ISBN: 978-09648837-1-0.

Website, D2L, Blog & Twitter

 The URL for the course website is http://oakton.chadlandrie.com. Some of the current content includes course descriptions; instructor contact information; i>clicker instructions and statistics; resources for the laboratory, lecture notes; and shared files available for download including rubrics, study guides and the course syllabus. Most of these resources will also be available on D2L.

In addition to the resources above, D2L will be used to make class announcements, disseminate updates to the class schedule and to post scores, curves and estimated grades. Be sure to setup your D2L notifications so that you are alerted when a news item is posted, when schedule has changed or when grades are updates.

An online database of all chemicals used in our experiments can be found at: http://stockroom.chadlandrie.com/. Relevant information includes physical properties, structure, hazard and safety information, GHS statements, NFPA symbols and spectra (infrared, ultraviolet-visible and mass spectrum).

A blog (http://chadlandrie.blogspot.com/) and Twitter feed (@chadlandrie) will also be maintained. I aim to use both mediums to educate students about current news in scientific fields, highlight career opportunities and to initiate discussions in organic chemistry. These are for personal interest only and are not course requirements.

II. Prerequisites

Successful completion of CHM 221 or CHM 223 with minimum grade of C or consent of instructor.


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III. Course Description

Course is second of two-course sequence (CHM 221/223 and CHM 222/224). Content includes study of structure, nomenclature, properties and reactions of alcohols and phenols, aldehydes and ketones, carboxylic acids and their derivatives, amines, condensation reactions, polymers, and bio-molecules. Weekly hands-on lab activities including preparations, separations, and identifications of organic compounds. Identical to CHM 222 except that CHM 224 includes two three-hour labs per week, rather than one three-hour lab per week.

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IV. Learning Objectives

Lecture Objectives

  1. Determine the Keq of acid-base reactions using pKa values; predict appropriate bases required to deprotonate common functional groups such as alkynes, phenols, alcohols and carbonyls.
  2. Apply the three models of bonding–Lewis, valence bond and molecular orbital theory–as well as their extensions–hybridization and resonance–to describe covalent bonding in organic species and to explain phenomena such as the Burge-Dunitz angle of nuclephilic addition to carbonyl, the anomeric effect
  3. Draw and interconvert drawings of neutral and charged organic species as well as biomolecules such as saccharides and amino acids, using condensed formulae, bond-line formulae, Newman projections, sawhorse projections, Hawthorn projections and Fisher projections.
  4. Name organic molecules and functional groups using systematic nomenclature defined by the International Union of Pure and Applied Chemistry (IUPAC).
  5. Rank organic species according to physical and chemical properties, including polarity, boiling point, acidity, solubility, bond strength, enol content, nucleophilicity, electrophilicity, stability and reactivity, based on their structural features.
  6. Draw mechanisms and their transition states for radical reactions and polar reactions using curved-arrow notation; rationalize regio, stereo and chemoselectivity using transition state analysis.
  7. Design synthetic routes to organic molecules and biomolecules, such as amino aicds and carbohydrates, using retrosynthetic analysis and an appropriate protecting group strategy.
  8. Propose reasonable biological pathways and mechanisms for anabolic and catabolic processes including fatty-acid biosynthesis, terpenoid biosynthesis, pyridoxal phosphate reactions, prostaglandin biosynthesis, glycolysis, thiamine catalyzed pyruvate decarboxylation and the citric acid cycle.
  9. Summarize methods for the preparation of ethers and thioethers from alcohols and phenols and thiols.
  10. Predict the products of nucleophilic addition reactions to carbonyls including cynohydrin formation, Grignard additions, hydration, acetal/hemiacetal formation, imine/enamine formation and the Wittig reaction.
  11. Predict the products of nucleophilic addition reactions of enols and enolates including Aldol, Claisen, Michael-addition and Diekman condensation.
  12. Compare and contrast the conditions under which thermodynamic and kinetic enolates are formed; predict the products of nucleophilic addition from each.
  13. Rationalize the relative reactivity of carboxylic acid derivatives and predict the products obtained upon nucleophilic acyl substitution to each.
  14. Summarize the structural and physical properties of amines and carboxylic acids; calculate the percentage of conjugate acid-base pairs in equilibrium in buffered and unbuffered aqueous solutions using the Henderson-Hasselbalch equation.
  15. Predict the products of amine reactions including alkylation, Gabriel amine synthesis, Curtius rearrangement, Hoffmann elimination, electrophilic aromatic substitution, diazonium formation.
  16. Differentiate, classify and characterize biomolecules including carbohydrates, amino acids, peptides, proteins, nucleic acids and lipids.
  17. Describe the structure and synthesis of organic polymers.

Laboratory Objectives

  1. Minimize risk to self and others by adhering to documented and verbalized laboratory safety policies.
  2. Operate instrumentation, such as an infrared spectrometer, melting point device, and polarimeter, independently to acquire data relevant to an experiment.
  3. Assemble glassware apparatuses to perform techniques such as distillation, extraction and chromatography.
  4. Document laboratory procedures, observations, analyses and conclusions in a laboratory notebook according to scientific standards.


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V. Academic Integrity

Student Academic Integrity Policy

All violations of The Code of Academic Conduct will be addressed according to the Student Academic Integrity Policy, both of which can be found in the Student Handbook. The student handbook may be accessed online at www.oakton.edu/studentlife. Disciplinary sanctions may include, but are not limited to, failing activity grade, failing course grade and suspension. Definitions of representative violations, taken from the Student Academic Integrity Policy, include:

a. Violations: Violations of the Code of Academic Conduct are activities (observed or reported) or materials whose character is deceitful and/or dishonest. All College employees, including full- and part-time faculty members, administrators, and Library, The Learning Center, Instructional Media Services, and Information Technology employees who are directly or indirectly involved in teaching or overseeing the academic work of students, are authorized—indeed, expected—to report violations of the Code of Academic Conduct. Students are also expected to report incidents of academic dishonesty that they witness to the appropriate faculty member, administrator, or other College employee and are encouraged to self-report any violations in which they have participated.
b. Abuse of Academic Materials: Destroying, stealing, or making inaccessible library, laboratory, or other academic resource material, or attempting to do so; stealing or otherwise obtaining advance copies of placement tests, examinations or other course materials or attempting to do so; duplicating copyrighted software without authorization or using such software on College computers; “hacking” on College computers or installing “virus” programs.
c. Bribes, Favors, Threats: Bribing or attempting to bribe, promising favors to, or making threats against any person, with the intention of affecting an evaluation of a student’s academic performance; conspire with another person who then performs one of these acts in one’s behalf.
d. Cheating: In any work submitted for evaluation (tests or assignments), copying or attempting to copy from another student’s work; using or attempting to use unauthorized information, notes, study aids, or other materials; any unauthorized collaboration with others, who may or may not be students, in work to be presented for a grade; altering graded work after it has been returned, then submitting the work to be re-graded; tampering with the academic work of other students.
e. Complicity in Academic Dishonesty: Helping another to commit an act of academic dishonesty, especially providing material or information to another person with knowledge that this material or information will be used deceitfully in an academic evaluation activity; permitting one’s own work to be submitted by another person as if it were that person’s original work.
f. Falsification and Fabrication: Altering transcripts, grade reports, or other documents affecting academic records; forging signature of authorization or falsifying information on any academic document, such as permission forms, petitions, or other documents.
g. Falsification of Records and Official Documents: Altering transcripts, grade reports, or other documents affecting academic records; forging signature of authorization or falsifying information on any academic document, such as permission forms, petitions, or other documents.
h. Personal Misrepresentation and Proxy: Taking another person’s place in an exam, placement test, or other academic activity, either before or after enrollment; having another person participate in an academic evaluation activity or evaluation in place of oneself.
i. Plagiarism: Presenting the work of another as one’s own (i.e., without proper acknowledgment of the source or sources) or submitting material that is not entirely one’s own work without attributing the unoriginal portions to their correct sources. The sole exception to the requirement of acknowledging sources occurs when ideas or information are common knowledge.

Course Policies

a. Academic Dishonesty: All violations of The Code of Academic Conduct will be addressed according to the Student Academic Integrity Policy.
b. Lecture Attendance: Students are expected to attend every lecture on-time. On-time is 2-5 minutes early. Attendance is recorded each time the i>clicker is used in class. There will not be opportunities to makeup i>clicker points that are lost due to absences. Lecture attendance will also be used at the end of the semester to evaluate students on the borderline of the course curves.
c. Laboratory Attendance: Attendance at all laboratory sessions is mandatory. Failure to attend a laboratory session will result in a score of zero for that lab's worksheet score. No laboratory experiments can be made up. Students with approved, extenuating circumstances (e.g., severe illness, death in the family) may be allowed to complete a supplementary assignment or worksheet pertaining to the missed experiment.
d. Laboratory Tardiness: Students who are more than 5 minutes late for a laboratory will not be allowed to participate and will receive a score of zero for that lab's worksheet score.
e. Missed Quizzes: Failure to take a quiz due to absence will result in a score of zero. No quizzes will be made up. At least 12 quizzes will be administered. Only the top ten scores will be counted.
f. Missed Exams: Failure to take an exam due to absence will result in a score of zero. No makeup exams will be given. If a student misses an exam and has an approved, and documented, extenuating circumstance, the final exam percentage will be used in place of the missing exam with a 5% deduction. (Missing exam % = Final Exam % - 5%)
g. Incompletes: Incompletes will not be given for students who have taken the final exam. Also, incompletes will only be granted for students showing proof of extenuating circumstances that prevented them from completing the course. Incompletes will not be given for students who are simply dissatisfied with their progress in the course or who are unable to handle their course load. When an incomplete is assigned, the work already completed and its respective scores will be used for evaluation (i.e., no work may be redone).
h. Exam/Quiz Errors: Students that suspect a grading or adding error on any exam or quiz must bring the original to my office for review within one week after the exam or quiz was returned.  A letter must accompany the exam that describes in detail what errors are suspected.  Exams and quizzes that have been written on or manipulated may not be submitted for review. Exams and quizzes submitted for review will not be returned; students should make a copy for their records.
i. Official Scores: Dr. Landrie maintains the official scores, point total and grades for each student.  The D2L course website is updated often, but may not reflect the official, current record. Students may see Dr. Landrie anytime during office hours to obtain a grade report with their current, official scores and estimated course grade.
j. Written Homework: Assignments and their due dates can be found on the class schedule. Two points will be deducted from the score for each day an assignment is late, including weekends. Extensions to these deadlines will only be granted when there are extenuating circumstances that can be documented. Students are expected to complete homework individually. While some amount of group work is expected and encouraged, blatantly copying answers from a peer is considered plagiarism and will be addressed according to the Student Academic Integrity Policy. Accept in the case of theft, all involved parties will be held responsible for plagiarism.
k. OWL Homework: OWL in an online homework platform. Assignments are organized by lecture. OWL assignments are available one day before the lecture and due one day after the lecture by 11:55 pm. For example, the OWL assignment for a Tuesday lecture is available at 12:05 am on Monday and due by 11:55 pm on Wednesday. Late submissions incur a penalty of 50%.
l. Laboratory Worksheets: Laboratory worksheets must be completed individually. Students will work in groups during the laboratory; however, all laboratory worksheets must be completed individually. Copying any part of a peer's worksheet will be considered plagiarism and will be addressed according to the Student Academic Integrity Policy. Accept in the case of theft, all involved parties will be held responsible for plagiarism.
m. Worksheet Deadlines: All worksheets are due the following class period regardless of whether a lab is completed that day. Late worksheets will be assessed a 2 point penalty per day.
n. i>Clicker Cheating: Under no circumstances may a student cast votes for another student. Students caught with more than one i>clicker during lecture will have the i>clickers in their possession confiscated. Users of all clickers confiscated will receive a zero for the i>clicker portion of the course.
o. Assigned Reading: Students are responsible for reading the textbook sections listed in the class schedule prior to the lecture covering those sections. Quizzes may cover assigned reading before the material is presented in lecture.
p. Laboratory Safety Procedures: Students must follow all laboratory policies and procedures outlined in this syllabus and in Appendix A of the laboratory manual. Failure to follow these safety protocols may result in a loss of laboratory notebook points (2 points per violation) or earned grade of zero for that laboratory and dismissal from the laboratory for severe violations (e.g. eating or drinking in the lab). Additionally, students are expected to read all hazard and safety information for the chemicals they will be using during the laboratory. These details can be found online at http:\\stockroom.chadlandrie.com.
q. Goggles: All students must wear goggles in the lab at all times when chemicals, glassware or instruments are being used or when instructed by the Professor. Students not wearing goggles will be warned once; subsequent violations will result in the loss of two points for each violation.
r. Email Communication: Dr. Landrie will send class announcements to students’ Oakton email address. Students are responsible for checking their D2L News feed and email at least once daily.

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VI. Outline of Course Topics

Lecture Topics

  1. Alcohols and Phenols
    1. Nomenclature and physical properties of alcohols
    2. Redox reactions of alcohols, ketones and aldehydes
      1. Swern and Dess-Martin; modern methods
      2. Chromium oxidations
      3. Periodic acid cleavage of diols
      4. Hydride reductions of aldehydes and ketones
    3. Silyl and benzyl protecting groups for alcohols
    4. Grignard addition to ketones and aldehydes
      1. Basicity of Grignards
      2. Protecting group strategies
    5. Extraction of phenols, carboxylic acids and amines in aqueous solutions
    6. Electrophilic aromatic substitution of phenols (O vs. C-acylation and alkylation)
  2. Ethers and Thioethers
    1. Nomenclature and physical properties of ethers
    2. Crown ethers and ethers as solvents (e.g., role in Grigard reagents)
    3. Conformational analysis of pyran rings
    4. Crown ethers; role in nucleophilic substitution
    5. Preparation of Ethers
      1. Williamson ether synthesis
      2. Alcohol condensation
      3. Epoxidation by peroxyacids
      4. Biological oxidation of arenes; NIH shift
      5. Claisen rearrangement
      6. Alkylation of thiols; S-adenosylmethionine
    6. Reactions of ethers
      1. Acidic cleavage
      2. Ring opening of epoxides (acidic and alkaline)
  3. Nucleophilic Addition Reactions to Aldehydes and Ketones
    1. Nomenclature and physical properties of aldehydes and ketones
      1. Carbonyl bond strength
      2. Carbonyl polarity and its influence on boiling point and solubility
    2. Reactions of Ketones and Aldehydes
      1. Hydration equilibrium; rationalize Keq of various substrates
      2. Hyperconjugation and inductive effect on ground state carbonyl stability
      3. Cyanohydrin formation equilibrium
      4. Benzoin condensation; Umpolung
      5. Condensation with amines: imines and enamines
      6. Acetal and hemiacetal formation
      7. Wittig olefination
  4. Carboxylic Acids
    1. Nomenclature and physical properties
    2. Acidity of carboxylic acids
      1. Substituent effects on pKa
      2. Substituent effects through benzene (Hammett plot)
    3. Synthesis of Carboxylic acids
      1. Oxidation of alcohols and aldehydes
      2. Nitrile synthesis
    4. Reactions of Carboxylic acids
      1. Fisher esterification
      2. Lactonization
      3. Decarboxylation of diacids and ketoacids
      4. Biological decarboxylations
  5. Carboxylic acid derivatives
    1. Nomenclature and physical properties
    2. Addition/elimination mechanism; tetrahedral intermediate
    3. Relative reactivity of derivatives
    4. Interconveresion of derivatives
    5. Thionyl chloride in synthesis
    6. DCC and mixed anhydride methods for preparing amides
    7. Amine chemoselectivity vs. alcohol
    8. Saponification and transesterification; soap and biodiesel
    9. Grignard addition to esters and nitriles
    10. Biological reactions of thioesters; rationalizing nature’s choice
  6. Enols and Enolates
    1. Mechanism of enolation
    2. Relative acidity of carbonyl compounds
    3. Kinetic vs. thermodynamic enolates
    4. Reactions of enols and enolates
      1. Aldol, Claisen, Dieckman, acylation, alkylation
      2. Malonic ester synthesis
      3. Conjugate additions: cuprates vs. Grignards
      4. Michael addition, Robinson annulation
      5. Hell-Volhard-Zelinski monohalogenation of enols
      6. Haloform reaction of enolates
    5. Enolization and enol content (equilibrium)
  7. Amines
    1. Classification, nomenclature and physical properites
    2. Basicity of alkyl amines, aryl amines and amidines (imidazole and DBU)
    3. Amines at physiological pH (Henderson-Hasselbalch)
    4. Solubility and extraction of amines
    5. Synthesis of amines
      1. Lithium aluminum hydride reduction of amides and azides
      2. Amine alkylation; quaternary salts
      3. Gabriel amine synthesis
      4. Curtius rearrangement
      5. Hoffmann elimination rule/transition states
      6. Role as electron donating group in electrophilic aromatic substitution
      7. Formation of diazonium ions; Sandmeyer reactions
  8. Carbohydrates
    1. Classification and nomenclature
    2. Fisher projections; D and L monosaccharides
    3. Anomers of pyranoses and furanoses
    4. Mutarotation, optical rotation and the anomeric effect
    5. Redox reactions of carbohydrates
    6. Chain extension through cyanohydrins
    7. Chain shortening through Wohl degradation
    8. Glycoside synthesis by Koenigs-Knorr
    9. 1,4 and 1,6-disaccharides
  9. Amino Acids
    1. Classification
    2. Using Henderson-Hasselbalch to determine the major form at specific pH
    3. Calculate isoelectric point (pI)
    4. Synthesis of amino acids
      1. Hell-Volhard-Zelinski
      2. Reductive amination
      3. Acetamidomalonate synthesis
  10. Peptides and Proteins
    1. Classification
    2. Sequencing
      1. Sanger’s reagent
      2. Ninhydrin staining
      3. Edman degradation
      4. Enzyme hydrolysis
    3. Synthesis
    4. Amino acid protecting groups strategies
    5. DCC coupling
  11. 11. Lipids
    1. Definition and classification
    2. Prostaglandins, steroids, triglycerides, waxes, phospholipids, fats and terpenes
  12. Chemistry of metabolic pathyways
    1. NIH shift
    2. ATP
      1. Structural basis for phosphorylation potential
      2. Phosphorylation mechanism
      3. Role in coupled reactions; shift Keq b 10^8
    3. Fatty-acid biosynthesis
    4. Prostaglandin biosynthesis
    5. Monoterpene biosynthesis
    6. Glycolysis
    7. Citric acid cycle
  13. Polymers

Laboratory Experiments

The laboratory activities and experiments can be found in the laboratory manual for the course.

Check-in & Safety
Exp. 32: Fermentation of Sucrose

Exp. 33: Properties and ID of Alcohols

Exp. 31: Gringard Addition

Exp. 34: Preparation of Benzoin

Exp. 35: Preparation of Benzil

Exp. 37: Hydrolysis of Benzonitrile

Exp. 38: Nomenclature of Acid Derivatives Drill

Exp. 39: Preparation of Benzocaine

Exp. 41: Preparation of DEET

Exp. 42: Aldol Condensation Reaction

Exp. 44B: Reduction of 3-Nitroacetophenone with Sn and HCl

Exp. 46: Identification of an Unknown Sugar

Exp. 47: Isolation of Casein from Milk

Exp. 48: Properties and Identification of Amino Acids

Exp. 49: Preparation of Soap

Exp. 50: Electrophoresis

Exp. 51: Polymers

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VII. Methods of Instruction

a. Lectures: Lectures will be presented using digital presentation software and an overhead projector. The lecture topics will be taken from the current course textbook as well as from outside sources at the instructor’s discretion. Following class, lecture will be posted on the course website for students to download.
b. i>Clicker: i>Clicker questions will be asked during each lecture; students will vote on the correct multiple choice answer using their i>clickers. These questions will also serve to initiate discussion and to measure whether concepts are being understood as they are taught.
c. Skill Builder Exercises: Several times throughout the semester, the lecture period will be used to complete activities designed to help students master problem solving in organic chemistry. The activities will be completed in groups and as a class to give students the opportunity to observe how others, including the instructor, solve organic chemistry problems.
d. Homework: The instructor will develop written homework assignments that compliment the lecture and textbook material. Since all questions are not graded for correctness, it is the student's responsibility to ensure each question is mastered by studying solutions to similar problems, working with colleagues and seeking assistance from the instructor.

e. Laboratory Experiments: Students will conduct several experiments in organic chemistry designed to connect the concepts learned in lecture to practical experiences. These experiments will include learning analytical techniques, such as melting point determination, thin-layer chromatography, gas chromatography, NMR spectroscopy, infrared spectroscopy and gas chromatography. Students will also synthesize organic compounds using classical and contemporary chemical reactions in organic synthesis.
f. D2L Multimedia Multimedia such as practice worksheets, handounts, instructional videos and practice quizzes will be posted to D2L.

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VIII. Course Practices Required

a. Writing Skills: Students are expected to write at the college level on homework, exams and written assignments. College level writing includes adherence to rules of grammar, the ability to organize thoughts into a logical order using cohesive paragraph structures, and legible handwriting for written assignments.
b. Communication Skills: Students are expected to communicate the language and ideas of organic chemistry orally as well through their writing. All students will be asked to answer questions during class and to participate in discussions and oral presentations. Students are also responsible for communicating with their peers and their instructor when they need help. Students are encouraged to ask questions and to seek out answers to help them master the course content.
c. Computer Skills: Students will require basic computer skills to complete homework assignments, to complete written assignments using a word processor, to search the academic literature using online databases, to access the course website and to view their course grades using the D2L online course management system and to communicate with the instructor through email. Students are required to check their email once daily to stay apprised of course announcements.
d. Organization and Time Management: Students are responsible for checking the class schedule to determine when assignments are due, what advanced reading is required prior to each lecture and when exams and quizzes will be given. Students are expected to read the listed sections in the schedule before they are covered in lecture. Students are responsible for using the class schedule to plan their studying activities prior to quizzes and exams. Students are responsible for determining when prelab entries must be completed in their lab notebooks.
e. Critical Thinking: Students are expected to solve problems in organic chemistry that require them to summarize, analyze, and apply concepts. While memorization is an important skill and needed in parts of the course, it is not the primary method of learning and success cannot be obtained solely through it.


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IX. Instructional Materials

Current textbook information for each course and section is available on Oakton’s Schedule of Classes. i>Clickers may also be purchased from third parties, new or used, or borrowed from friends not using the clicker during that particular semester.

1. Required: McMurray, J. Organic Chemistry, 9th ed.; Cengage: Boston, MA, 2016. ISBN: 978-1-305-08048-5 (hardcover) or McMurray, J. Organic Chemistry Loose Leaf with OWL, 9th ed.; Cengage: Boston, MA, 2016. ISBN: 978-1-305-70102-1 (loose-leaf) .

mcmurray9th

2. OWLv2. This is the Cengage online homework platform. An access code is bundled with the loose-leaf text sold by the Oakton Bookstore. It can also be purchased directly from Cengage. Follow instructions within D2L. Access code required after 14-day trial period.


3. Required: CHM 222/224 – Organic Chemistry II Laboratory Experiments.

223cover

4. Student Lab Notebook, Hayden-McNeil, ISBN: 978-1-930882-74-4 (Or similar; Must be spiral-bound and contain at least 50 pages)


5. Required: Chemical splash goggles (indirectly vented). The goggles must seal completely around the face. Shield-type or glasses-type are not allowed.

goggles

6. Recommended: i>Clicker (1 or 2); MacMillan (www.iclicker.com); ISBN: 1429280476. If students do not wish to purchase their own i>Clicker, one will be loaned to them at the beginning of each class.

iclicker

7. Recommended: Molecular model set. Preferred set is “MOLECULAR VISIONS Organic, Inorganic, Organometallic” in a green plastic box. Sold by Darling Models, INC. ISBN: 978-09648837-1-0.

models

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X. Methods of Evaluating Student Progress

Summary of Point Distribution

The course will be graded according to individual performance on each of the following assessment items:

  Course Activity Points   No.   Total Points Weight
a. i>Clicker 30 X 1 = 30 3% 
b. Homework - Written 4 X 10 = 40 4%
b. Homework - OWL 2 X 30 = 60 6%
c. Quizzes 10 X 10 = 100 10%
d. Skill Builder 5 X 10 = 50 5%
e. Semester Exams 100 X 3 = 300 30%
f. ACS Exam 70 X 1 = 70 7%
g. Final Exam 200 X 1 = 200 20%
h. Laboratory Worksheets 100 X 1 = 100 10%
h. Laboratory Exam 50 X 1 = 50 5%
  Total         1000 100%


Description of Graded Course Activities

a. i>Clicker The i>clicker will be used in most of the lectures this semester. Generally, 5-10 questions will be asked during each lecture to reinforce a concept just covered or to determine if I have done a sufficient job of explaining a topic.  These questions will appear on the projector screen as part of the lecture slides.  One point will be awarded to each student that answers the question; one additional point will be given for the correct answer.  The questions may be reviewed later by downloading the lecture slides or by viewing the i>clicker page within the course website.  At the end of the semester, the accrued number of i>clicker points will be converted to a scale with a total of 30 course points (3%).
b. Written Homework Homework will be assigned that covers the material presented in the lecture and textbook readings. Each homework assignment is worth 10 points. Students will receive a maximum of six points for completion. One point will be subtracted for each incomplete or missing question for a maximum of a six-point deduction. A random set of questions will be graded out of four points for correctness.
c. OWL Homework OWL is an online homework platform. Many of the problems are the same as those found in the textbook. There is approximately one assignment for each lecture in the course. Problems will encourage student mastery by allowing multiple attempts, providing hints and embedding links to the Ebook and other resources.
d. Quizzes Quizzes will be given on the dates listed in the class schedule. At least ten quizzes, each worth 10 points will be assigned. The top ten scores will count toward the final grade. Quizzes will test mastery of topics presented in previous lectures as well as the assigned reading that should be completed prior to each lecture.
e. Skill Builder Five times during the semester, the lecture period will be used to complete activities designed to help students master problem solving in organic chemistry. The activities will be completed in groups and as a class to give students the opportunity to observe how others, including the instructor, solve organic chemistry problems. Each Skill Builder is worth 10 points and is graded primarily on participation and completion. Some elements of the Skill Builder may be graded on correctness, depending on the activity.
f. Semester Exams Exams will cover material presented during lecture as well as assigned readings. Question formats will include drawing reactants or products in reaction schemes, multiple choice, short answer, essay, drawing reaction mechanisms and ranking. Skill builders, quizzes, homework and i>Clicker should be used as examples of each question type. A study guide listing the topics, questions types and approximate point distribution will be distributed one week prior to each exam.
g. ACS Exam The American Chemical Society exam is multiple choice. A study guide developed by the ACS will be distributed one week prior to the exam. The exam will be used mainly to ensure that all sections are meeting minimum standards for proficiency in organic chemistry.
h. Final Exam The final exam is cummulative. The format of the exam will be similar to the three semester exams. A study guide will be distributed one week prior to the exam.
i. Laboratory Worksheets For each experiment, students will complete a laboratory worksheet in which they will summarize hazard and safety information for the chemicals used, record data and observations during the experiment and answer questions pertaining to the experiment. These worksheets should be used to prepare for the lab exam. Lab notebook entries (e.g, procedure and observations) will be included.
j. Laboratory Exam A laboratory exam will be administered at the end of the term. It will cover the theory, techniques and results of the experiments performed.

Course Evaluation, “The Curve"

The word “curve” means many different things to many different people. This course is not graded on a traditional Bell curve. In other words, there is no set number of As, Bs, Cs and Ds that must be earned. However, I will determine the minimum point values required to earn a letter grade for each component of the course. These limits will not be determined in advance since I cannot predict the difficulty of exams and quizzes and do take into account how well I’ve taught a topic or explained an assignment. Students may gauge their progress by viewing the limits on the course website for each course component as well as the course total. These limits vary slightly each semester since variations in exam difficulty, teaching quality and grading styles cannot be avoided. Students may also see me during office hours for an up-to-date grade report. Having said that, the anticipated cutoffs for the final course grade is:

80%, 800 pts, A
70%, 700 pts, B
55%, 550 pts, C
45%, 450 pts, D

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XI. Other Course Information

Students with Disabilities

If you have a documented learning, psychological or physical disability, you may be entitled to reasonable accommodations or services. To request accommodations or services, contact the Access and Disability Resource Center at the Des Plaines or Skokie campus. All students are expected to fulfill essential course requirements. The College will not waive any essential skill or requirement of a course or degree program. For more information or to request accommodations, contact the ADRC at:

URL: http://www.oakton.edu/studentservices/disability_services/index.php
Location: Rm 2400 Des Plaines Bldg
Phone: 847-635-1667

Religious Holidays

Oakton Community College recognizes the broad diversity of religious beliefs of its constituencies. The college has embraced a practice of shared responsibility in the event a religious observance interferes with class work or assignments. Students who inform instructors in advance of an intended absence for a major religious observance will not be penalized. The instructor will make reasonable accommodation for students, which may include providing a make-up test, altering assignment dates, permitting a student to attend another section of the same course for a class period or similar remedies. Instructors are not responsible for teaching material again. Instructors should inform students of this practice at the beginning of the semester so that arrangements can be made accordingly. Similar consideration is accorded to faculty, staff and administrators and is provided for in their respective contracts.

Title IX

Oakton Community College is committed to maintaining a safe campus environment emphasizing the dignity and worth of all members of the community and complies with all Title IX requirements.

Resources and support for
  • • pregnancy-related and parenting accommodations; and
  • • victims of sexual misconduct
can be found at http://www.oakton.edu/title9

Change of Health Status

Students who have a change of health status need to contact me as soon as possible. For accommodations specifically related to pregnancy or post-pregnancy-related parenting, contact me and consult the Title IX policy at http://www.oakton.edu/title9. If you are pregnant or become pregnant during the semester, you have the option to meet with me to discuss reasonable accommodations that may be necessary. It may not be possible to grant accommodations after the fact, so it is better to prepare in advance for any possible scenarios.

Students First

Oakton has implemented an academic intervention program, and I am a participating faculty member. I am committed to your success in this course and at this college. I may, therefore, refer you to other individuals and/or services available to help you achieve academic success. Please understand that these referrals are intended to supplement, not replace, interactions you may have with me during office hours or in class. They are intended to provide a support network for your academic and personal success at the College. As such, please help us help you by responding promptly and appropriately to these referrals. If you have any questions regarding this program, please don’t hesitate to ask.

Emergency Building Closures

When an Oakton building is closed due to an emergency (e.g., weather-related closings), that doesn't mean instruction stops. Students should check for communications from their instructor via D2L, other learning environments such as myMathlab, or via email or text. If you don't receive communication from your instructor within 24 hours of building closure, please contact them.

Recording Policy

Electronic video and/or audio recording is not permitted during class unless the student obtains written permission from the instructor. In cases where recordings are allowed, such content is restricted to personal use only. Any distribution of such recordings is strictly prohibited. Personal use is defined as use by an individual student for the purpose of studying or completing course assignments.

For students who have been approved for audio and/or video recording of lectures and other classroom activities as a reasonable accommodation by Oakton’s Access Disabilities Resource Center (ADRC), applicable federal law requires instructors to permit those recordings. Such recordings are also limited to personal use. Any distribution of such recordings is strictly prohibited.

Failure to abide by this policy will result in disciplinary action through the Code of Student Conduct.


Lecture and Laboratory Schedules

The lecture and laboratory schedules can be found here. They will be updated weekly as changes are made. Student will also receive notifications in class and through the D2L News items when changes are made to the schedule.

Important Dates

All of the dates below can be found in the College’s Academic Calendar.

Date Item
1/13/2020
Faculty Return
1/21/2020
Spring 2018 Classes Begin
2/18/2020
Last day to withdraw from 16-week courses and have course dropped from record
2/18/2020
Last day to to change to audit for 16-week courses.
2/21/2020
Last day for filing graduation petitions
2/17/2020
Presidents Day Holiday, College Closed
3/1/2020
Incomplete (I) grades from summer 2013 semester for which faculty have not submitted final grades will become an "F" after this date.
3/16-3/22/2020
Spring Break
3/30/2020
Last day to withdraw with a "W" from 16-week courses.
3/23/2020
Classes Resume
3/25/2020
Registration opens for summer 2020 semester.
4/8/2020
Registration opens for fall 2020 semester.
5/15/2020
Last day of student attendance
5/18/2020
Grading day. Faculty on campus and available to students at designated times.
5/19/2020
Faculty grading due.
5/18/2020
Commencement
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