PELLISSIPPI STATE TECHNICAL COMMUNITY COLLEGE 
MASTER SYLLABUS
APPLIED ORGANIC CHEMISTRY W/ LAB
CHT 2210
Class Hours:  3.0   Credit Hours:  4.0  
Laboratory Hours:  3.0   Date Revised:  Fall 2001  
NOTE:    This course is not designed for transfer credit.
       
Catalog Course Description:    
  A study of  the physical and chemical properties of organic compounds with strong emphasis on understanding organic reaction mechanisms.  Memorization will be subordinated and strong emphasis placed on understanding the conditions that affect the initiation and rate of organic reactions.  Organic chemical nomenclature will be studied, and the use and production of organic chemicals in local industries will be surveyed.  Course includes three hours of lecture and three hours of laboratory applications each week.
Entry Level Standards:    
  Entering students should have a grasp of general chemistry.
Prerequisite:    
  CHT 1120
Textbook(s) and Other Reference Materials Basic to the Course:  
  Hart, Crane, and Hart. Organic Chemistry - A Short Course. 10th ed. Houghton Mifflin Co. 
Laboratory Manual: Hart, Crane, and Hart.  Organic Chemistry - A Short Course. 10th ed. Houghton Mifflin Co.
I. Week/Unit/Topic Basis:    
  Week  Topic
  1 Lecture: History of organic chemistry 
Lab: Recrystallization of acetanilide - Objective:  demonstrate the methods used to recrystallize materials and measure melting point.
  2 Lecture: Alkanes (free radical reactions) 
Lab: Polymerization of styrene - Objective:  demonstrate a free radical reaction and estimate molecular weight by measuring toluene solution viscosity.
  3 Lecture: Alkanes (free radical reactions) 
Lab: Preparation of cyclohexene from cyclohaxanol - Objective:  demonstrate the removal of an unsymmetrical product thru the reverse of an electrophillic addition reaction across a double bond.
  4 Lecture: Alkenes (Markovnikov's rule)(orbital symmetry) 
Lab: Friedel Crafts alkylation of toluene - Objective:  demonstrate the aromatic electrophillic substitution reaction.
  5 Lecture: Alkenes (Markovnikov's rule)(orbital symmetry) 
Lab: Synthesis of  t-butylchloride - Objective:  demonstrate an SN1reaction.
  6 Lecture: Aromatic compounds(aromatic substitutions) 
Lab: Synthesis of n-butylbromide - Objective:  demonstrate an SN2 reaction.
  7 Lecture: Aromatic compounds(aromatic substitutions) 
Lab: Synthesis of a benzoic acid by the oxidation of toluene - Objective: demonstrate the oxidation of an aromatic side chain.
  8 Lecture: Halogens (Nucleophilic substitution and elimination) Solubility of organic compounds 
Lab: Cannizaro reaction using benzaldehyde - Objective:  demonstrate a hydride ion transfer reaction.
  9 Lecture: Halogens (Nucleophilic substitution and elimination) Solubility of organic compounds 
Lab: Aldol condensation
  10 Lecture: Alcohols, Phenols and Thiols 
Lab: Esterification
  11 Lecture: Ethers and epoxides (Grignard reaction) Carbocation rearrangement 
Lab: Grignard reaction
  12 Lecture: Aldehydes and ketones (hydride transfer reactions) Ionic elimination and addition reactions 
Lab: Cis-trans isomerization
  13 Lecture: Carboxyllic acids (esterification) 
Lab: Nylon rope trick
  14 Lecture: Amines and other nitrogen compounds. Heterocyclic compounds. 
Lab: Diels-Alder reaction
  15 Lecture: Polymers 
Lab: Chromatography
  16 Lecture: Final Exam 
Lab: No lab
II. Course Objectives*:    
  A. Learn the relationship between molecular bonding and organic chemical structure. I, II
  B. Learn the nomenclature rules for simple organic compounds. II, IV
  C. Sketch structures for simple organic compounds.  II, IV
  D. Learn the methods for describing stereoisomers. II, IV
  E. Understand the common reaction mechanisms in organic reactions. I, II, III
  F. Understand the basis for organic chemical solubility. I, II, III
*Roman numerals after course objectives reference goals of the Chemical/Environmental Engineering Technology program.
III. Instructional Processes*:     
Students will:      
  1. Attend lectures and discuss concepts.  Communication Outcome, Problem Solving and Decision Making Outcome, Information Literacy Outcome, Active Learning Strategy
  2. Solve assigned problems out of class and be prepared to discuss the problem solutions.  Communication Outcome, Problem Solving and Decision Making Outcome, Numerical Literacy Outcome, Information Literacy Outcome, Active Learning Strategy
  3. Do library research on assigned topics.  Communication Outcome, Problem Solving and Decision Making Outcome, Technological Literacy Outcome, Information Literacy Outcome
  4. Participate in laboratory experiments which are direct applications of the concepts studied.  Communication Outcome, Problem Solving and Decision Making Outcome, Technological Literacy Outcome, Information Literacy Outcome, Active Learning Strategy, Transitional Strategy
  5. Perform laboratory experiments, collect data and keep a research style lab notebook.  Communication Outcome, Problem Solving and Decision Making Outcome, 4 Cultural Diversity and Social Adaptation Outcome, Technological Literacy Outcome, Information Literacy Outcome, Active Learning Strategy
  6. Use a computer program for naming organic compounds and drawing structures.  Communication Outcome, Problem Solving and Decision Making Outcome, Technological Literacy Outcome, Information Literacy Outcome, Active Learning Strategy
  7. Use models to visualize organic chemical structures.  Problem Solving and Decision Making Outcome
*Strategies and outcomes listed after instructional processes reference Pellissippi State’s goals for strengthening general education knowledge and skills, connecting coursework to experiences beyond the classroom, and encouraging students to take active and responsible roles in the educational process.
IV. Expectations for Student Performance*: 
Upon successful completion of this course, the student should be able to:
1. Describe the types of bonds in organic compounds.  A
2. Name simple alkanes.  B
3. Name branched alkanes.  B
4. Name simple alkenes and alkynes.  B
5. Name substituted benzene compounds.  B
6. Name substituted naphthalene compounds.  B
7. Name cyclic alkanes and alkenes.  B
8. Name simple alcohol compounds.  B
9. Name simple aldehyde compounds.  B
10. Name simple ketone  compounds.  B
11. Name simple carboxylic acid compounds.  B
12. Name simple amines.  B
13. Name simple amides.  B
14. Name simple nitro compounds.  B
15. Name simple amino acids.  B
16. Name heterogeneous ring compounds.  B
17. Illustrate the various methods used to depict molecular structures.  C
18. Draw structural diagrams for alkenes and alkanes.  C
19. Draw structural diagrams for cyclic compounds, including ortho, meta and para compounds.  C
20. Draw structural diagrams for cis-trans isomers.  C
21. Draw structural diagrams for enantiomers.  C
22. Draw structural diagrams illustrating the RS convention.  D
23. Draw structural diagrams illustrating the EZ convention.  D
24. Draw diagrams illustrating multiple chiral centers in sugars and polysaccharides.  D
25. Show-using structural diagrams- why materials may be racemic mixtures.  D
26. Describe the rotation of polarized light by compounds.  D
27. Describe the free radical reaction mechanism.  E
28. Show possible free radical reaction steps in forming a chlorinated alkane.  E
29. Give examples of initiation, propagation, transfer and termination reactions.  E
30. Describe free radical polymerization of monomers.  E
31. Describe the reaction mechanism for electrophillic addition to alkenes.  E
32. Explain the distinction between primary ,secondary ,and tertiary carbocations.  E
33. Explain why Markovnikov's rule works.  E
34. Describe the first order nucleophilic substitution reaction mechanism.  E
35. Describe the second order nucleophilic substitution reaction mechanism.  E
36. Explain the differences between first order and second order nucleophilic reactions.  E
37. Describe hydrogen bonding.  E
38. Describe the common ion effect.  E
39. Explain the difference between protic and aprotic solvents.  E
40. Describe the electrophillic aromatic substitution reaction mechanism.  E
41. Describe the carbanion rearrangement reaction mechanism.  E
42. Describe the hydride transfer reaction mechanism.  E
43. Explain the reason for selectivity of isomers in no-mechanism reactions.  E
44. Explain why thermal and light initiation of reactions give different reaction products.  E
45. Explain the how polarity and dielectric constant can be used to predict solubility of organic compounds.  F
*Letters after performance expectations reference the course objectives listed above.
V. Evaluation:
A. Testing Procedures: 65%of grade
25% of the course grade will be determined by the laboratory and 75% by the classroom.  Evaluation of classroom work will be based on 3 or more exams, homework assignments, and comprehensive final exam.   Exams and papers will comprise 35% of the course grade and the final will comprise 30% of the course grade. There is no provision for missing an exam because of lack of preparedness. 
B. Laboratory Expectations: 25% of grade
Evaluation of laboratory work will be based on the laboratory notebook.  The notebook will be maintained in the style of an  industrial notebook used for patent purposes. Products and reactants will be analyzed in each experiment by each student using the Fourier transform infrared spectrometer (FAIR) and the gas chromatography with mass spectrometer detector (GCMS) where appropriate and as limited by machine availability. 
C. Field Work: 10% of grade
To encourage homework completion, all homework turned in will be given a grade of A up to 10% of the course grade (see formula below). Outside readings and library research will be required in this course.
D. Grading Scale:
The course grade will be calculated using the formula below: 
G=10*H/HM + (.35*(T (1) + T(2) +...T(N))/N + .30* F)/(.9 + .1*H/HM) + .25*L 
            where  G  = the numerical grade 
                        H  = the homework grade 
                     HM = the maximum homework grade attainable 
                     T( i )= the grade on exam number i (Research  papers are included in  
                                       this category.) 
                        N  = number of exams and research papers  (excluding the final exam) 
                         F  = the grade on the final exam 
                         L  = the laboratory grade. 

Letter grades will be awarded based on the following schedule: 
90 – 100       A 
87 – 89         B+ 
80 – 86         B 
77 – 79         C+ 
70 – 76         C 
60 – 70         D 
below 60      F
VI. Policies:
A. Attendance Policy:
Pellissippi State Technical Community College expects students to attend all scheduled instructional activities.  As a minimum, students in all courses must be present for at least 75 percent of their scheduled class and laboratory meetings in order to receive credit for the course (Pellissippi State Catalog).  Individual departments/programs/disciplines, with the approval of the vice president of Academic and Student Affairs, may have requirements that are more stringent. 
Chemical/Environmental Engineering Technology Program: 
Regular attendance in this course is required.  Students who miss the equivalent of 10% of either classroom hours or laboratory may, at the discretion of the instructor, have their course grade dropped by one letter.  Students who arrive late for a class after the roll as been called have the responsibility of seeing the instructor after class the change their status from A (absent) to T (tardy).
B. Academic Dishonesty:
In keeping with college-wide policies, the student is expected to adhere to the general rules and regulations relevant to academic and classroom misconduct as outline in the catalog.