Syllabus for Chemistry 201

Organic Chemistry 201 Section 4275                               Fall 2006

 

Instructor: Dr. Nadene Houser-Archield

Office: Chesapeake Hall 310J

Phone: 301 386 7593

E-Mail: nhouser_archield@pgcc.edu (note: the space between nhouser and archield is an underscore _)

Office hours:  T 9:00-9:50am and 5:00-5:50pm                         Th 9:00-9:50am and 3:30 – 6:30pm                 

 

Class Meeting Times:   Lab  T  6:00 - 9:30 pm   CH 320

                         

Final Exam:  Tuesday, December 12, 2006, 6:00 – 9:30pm   CH 320

 

Course Materials:                    

Blackboard notes, exercises and handouts.  For directions go to http://www.pgcconline.com ; select Announcements for Students.

Textbook:         Organic Chemistry, 6th Edition by John McMurry

            Lab manual:      Experiments and Activities in Organic Chemistry by

                                    Nadene Houser-Archield

            Molecular Model kit: Not mandatory but strongly suggested. The University of Maryland, College Park bookstore sells several varieties.

            Supplemental    Practical Spectroscopy: The Rapid Interpretation of Spectral Data for

            Manual:            McMurry’s Organic Chemistry, 5e. ISBN 0-534-37230-9

Safety Goggles (these are provided free of charge, in the lab)

 

Welcome to Chemistry 201!

            This course is designed to immerse you in the basic tenets of organic chemistry. Laboratories, lectures, workshops and demonstrations will be the modes of information dispersal and skill acquisition. 

            In order to be successful, read the chapters (prior to lecture is best), attend each lab, lecture and workshop, do the suggested homework problems and join/form a regularly meeting study group. You will need approximately 20 hours of study per  week!!! I am available during office hours. Also, the College provides free tutoring services by appointment on the third floor of Accokeek Hall. Stop in or call 322-0748 for an appointment.  I strongly suggest forming study groups; those students who are strong in chemistry enhance their knowledge by teaching others; those who are weak in chemistry enhance their knowledge by being exposed to the way others view the course concepts.

            Quizzes, exams, workshops, labs and the final exam will not be made up.  Cheating on an assessment will result in a grade of zero for that assessment; the cheating will be reported to the office of records.

Bring your calculator with you to lab.

Visit the Department of Physical Sciences and Engineering website at http://academic.pgcc.edu/psc


Objectives for Chemistry 201

 

Upon completion of this course a student will be able to:

 

1) Categorize bonds according to polarity [ionic or covalent (polar covalent or nonpolar covalent, also coordinate covalent)], composition (sigma or pi), orbital character ( percentage s,p,d character), strength (% ionic character; % s,p,d character; single, double or triple; amount of overlap).

 

2) Apply principles of Valence Shell Electron Pair Repulsion theory to chemical formulas to determine Lewis dot structures, structural formulas, geometries and bond angles around central atoms, hybrid states of atoms, polarities of molecules and formal charges of atoms in molecules.

 

3) Employ structural formulas, classes, molar masses, polarities and/or types of interparticle forces and percentage hydrocarbon in compounds to predict states of matter, relative boiling and melting points, solubility properties, density, and flammability of compounds.

 

4) Employ resonance and/or inductive effects to determine electron richness or poorness of atoms.

 

5) Rank conformations according to stability/energy (steric hindrance, angle strain, bond strain, ring strain, eclipsing strain) using chair invertomers or Newman, sawhorse and Haworth projections.

 

6) Distinguish among structural isomers, stereoisomers [diastereomers (geometric and non-geometric), enantiomers (uses Fischer projections) and applies cis/trans, E/Z, R/S labels.

 

7) Name compounds and/or draws structural formulas for acyclic and cyclic hydrocarbons [alkanes, alkenes, and alkynes; substituted benzenes (benzoic acid, styrene, phenol, toluene, aniline, and 1,2-disubstituted benzenes], organic halides, nitro compounds, amines, alcohols, thiols, disulfides, ethers, aldehydes, ketones, carboxylic acids, anhydrides, esters, amides.

 

8) Employ qualitative analysis (litmus, Fehlings, Tollens, bisulfite, bicarbonate, KMnO4, K2Cr2O7, flame, solubility, FeCl3, Br2, and TLC), instrumental analysis/spectroscopy (IR, mass spectroscopy, UV, 13C-NMR, 1H-NMR), elemental analysis, index of hydrogen deficiency to determine structures of molecules.

 

9) Rank organic acids, organic bases (and conjugate bases) according to strength

 

10) Analyze/evaluate/assess reactants, reaction conditions (solvent, temperature) to predict products for the following types of reactions: combustion, free radical substitution (optional), oxidation (of alkenes, alkynes, alcohols, aldehydes and thiols), reduction [of alkenes, alkynes (poisoned catalyst too), disulfides] and acid-base reactions (of carboxylic acids, carboxylate salts, amines and ammonium salts).

 

11) Analyze/evaluate/assess SN1,  SN2, E1 and E2 reaction conditions (nucleophile/base, leaving group, solvent, steric hindrance, carbocation stability, base size) to predict products, reaction mechanisms, rearrangement, stereochemistry, regiochemistry, energetics (thermodynamic versus kinetic pathways and products), rate equations, molecularity and rate determining steps.

 

12) Analyze/evaluate/assess reaction conditions (carbocation stability, polarity of the addend, presence or absence of peroxides, temperature) to predict the products and regiochemistry of addition to alkenes and alkynes. 



Grading Scale: 

                                    A = 90-100%

                                    B = 80-89%                

                                    C = 70-79%               

                                    D = 60-69%               

                                    F = 59% and below or insufficient labs or final exam not taken

 

Note 1:      All labs are required!  If you perform fewer than 90% of the labs you will receive a grade of F in the course.

Note 2:      If you do not take the final exam, you will receive a grade of F in the course.

Note 3:      Assignments are due during the first minute of class.  Late assignments, if accepted, will be heavily penalized. If an assignment has already been graded and returned to the rest of the class, you can not turn it in for a late grade.

 

Assessment                                     Percentage of grade

Exams                                                              40%

Labs                                                                20%

Activities                                                          10%

Quizzes                                                            10%

Final Exam                                                       20%

Exams, quizzes, and labs will not be made up without official documentation such as emergency doctors’ notes, tow truck receipts timed and dated during the assessment period or funeral programs. If you are more than two minutes late for a quiz, you will not be allowed to take it or to make it up.

 

  Tentative Course Schedule

Week 1
8/28

Lab: Molecular Structure Activity (will be completed during the lab) and CHIME Activity (due at the beginning of the Week 5 lab; it counts as 1/2 lab)

Lecture: Review activities: Orbitals and Electron Configurations, The Periodic Table, Periodic Trends in Electronegativity.
Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.
Text ReadingChapters: 1.1-1.5  , 2.1-2.3, 2.12-2.13, 6.2

 

Week 2
9/4

Lab: Properties of Organic compounds and Melting points lab (due at the beginning of the Week 4 lab) and ChemSketch Activity (due at the beginning of the Week 4 lab; it counts as 1/2 lab)  

Lecture: Review Activities: formula mass and molar mass calculations, the octet rule, balancing equations and other review topics. 
Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.
Text Reading, Chapters 1.1-1.6, 2.3 , 2.1-2.3, 2.12-2.13, 15.3, 17.2

 

Week 3
9/11

Lab: 13 Unknowns (Part 1, qualitative analysis)

Lecture: Oxidation and Reduction, Quantitating Bond Polarity, Stoichiometry Review. Review reactions from 13 Unknowns lab.
Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.

Text Reading, Chapters: 1.1-1.6, 2.12, 2.13, 3.1-3.3, 3.5, 3.6, 6.1,  8.1, 10.10, 15.1, 17.2, 17.4, 18.2, p672-674, 19.3, p960

 


Week 4
9/18

Properties of Organic Compounds lab and ChemSketch Activity are due at the beginning of today’s lab.
Lab:  
1) Exam 1 (1 hour; see course objectives button on BlackBoard for the topics)
2)
13 Unknowns (Part 2, infrared spectroscopy): 13 Unknowns lab is due at the beginning of the Week 9 lab; it counts as 2 labs.

Lecture: Valence Shell Electron Pair Repulsion (VSEPR) Theory. Review reactions from the 13 Unknowns lab.

Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.

Text Reading, Chapters: 1.1-1.6, 2.12, 2.13, 3.1-3.3, 3.5, 3.6, 6.1,  8.1, 10.10, 15.1, 12.5-12.9, 15.10, 17.12, 18.11, 19.16, 20.10, 24.10

 

Week 5
9/25

CHIME Activity is due at the beginning of today’s lab; it counts as 1/2 lab.

Lab:

1) Barriers to Rotation Stereochemistry and Isomers laboratory activity (Part 1)

2) Newman projection Internet Activity: due at the beginning of the Week 7 lab; it counts as 1/2 lab.

Lecture: Hybridization and Organic Nomenclature. Review reactions from the 13 Unknowns lab.

Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.
Text Reading, Chapters: 1.6 – 1.11, 2.12, 2.13, 3.1-3.3, 3.4, 3.7, 6.3, 8.2, 10.1, 15.2, 17.1, 18.1, 19.1, 20.1, 21.1, 24.1

 

Week 6
10/1

Lab: Barriers to Rotation Stereochemistry and Isomers laboratory activity (Part 2)

Lecture: 1H NMR and Elemental Analysis. Review reactions from the 13 Unknowns lab.

Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.
Text Reading, Chapters: 4.1-4.3, 13.1-13.3, 13.8-13.13, 15.10, 17.12, 18.11, 19.16, 20.10, 24.10

Week 7
10/8

Newman projection Internet Activity due at the beginning of today’s lab; it counts as 1/2 lab.

Lab: Organic Acids and Bases and Extraction; due at the beginning of the Week 10 lab

Lecture: 13C NMR and Mass Spectroscopy.

Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.
Text Reading, Chapters: 6.6, 9.1-9.11, 12.1-12.4, 13.4-13.5, 13.7, 15.10, 17.12, 18.11, 19.16, 20.10, 24.10, 25.2-25.4 

 

Week 8
10/15

Mid-term

Lab: Exam 2

Lecture: Ultraviolet spectroscopy and a Model Spectroscopy exercise. Review Organic acids and bases and extraction lab and notes.

Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.

Text Reading, Chapters: 2.7-2.11, 5.2, 14.8-14.11, 15.10, 17.12, 18.11, 19.16, 20.10, 20.2-20.5, 24.4-24.5, 24.10

 

Week 9
10/22

 

13 Unknowns lab is due at the beginning of today’s lab; counts as 2 labs.

Lecture: Resonance and Inductive Effects. Review Organic acids and bases and extraction lab and notes.

Lab: No Lab College Enrichment Day for Faculty and Staff

Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.
Text Reading, Chapters: 1.12, 2.1-2.2, 2.4-2.6, 15.3-15.4

 

Week 10
10/29

Extraction lab: due at the beginning of today’s lab

Lab: Nucleophilic Substitution: due at the beginning of the Week 13 lab.

VSEPR Practical Practice

Lecture: Alkanes

Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.

Text Reading, Chapters: 3 and 4, 5.1 -5.3

 

Week 11
11/6

Lab: Elimination: due at the beginning of the Week 14 lab

Lecture: Nucleophilic Substitution and Free Radical Substitution. Solubility tests for the 2nd Extraction lab.

Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.

Text Reading, Chapters: 3.5, 5.1-5.4, 5.6, 6.7, 6.10-6.12, 10.4-10.7, 11-11.9, 18.3, p 904

 

 

Week 12

11/13

Nucleophilic Substitution lab due at the beginning of today’s lab.

Lab: Addition: due at the beginning of the Week 15 lab

Lecture: Elimination

Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.
Text Reading, Chapters: 5.1, 5.7-5.10, 6.4, 6.7, 8.3, 11.10-11.16 , 17.7-17.8

 

Week 13
11/20

Elimination lab: due at the beginning of today’s lab.

Lab: 2nd Acid-Base Extraction to be completed in lab

Lecture: Addition Reactions and Reactions of Alcohols

Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.
Text Reading, Chapters: 5.1,5.5, 6.8-6.12, 7.1-7.6, 7.7-7.8, 8.4, 8.6, 14.5-14.6, 18.4, 18.7, 18.10

 

Week 14
11/27

Addition lab: due at the beginning of today’s lab

Lab: Lab Practical; will be completed in the lab; counts as two labs

Lecture: Review

Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.

 

Week 15
12/3

Lab: Exam 3 and a VSEPR-Stereochemistry Practical

Lecture: Review

Objectives, Notes, Lab procedure(s) and Homework are on BlackBoard.

 

Week 16
12/10

December 12th 6:00 -9:30 am CH 320

Final Exam (2.5 hours, cumulative all topics, 40% synthesis)

Have a Wonderful Holiday!

 

 

 

 

My Philosophy

 

The numbers of students majoring in STEM (Science, Technology, Engineering and Math) disciplines is declining as nationwide the dropout/failure rate in STEM  courses, particularly in large lecture courses, averages 50% or higher. This trend must be reversed or it will harm our society, as we will have a shortage of qualified STEM professionals.

 

I combine elements of Piaget, Arlin, Hebb, Bloom and Bruner’s theories with some of my own reflections. I believe there are four domains of learning in order of increasing importance:

1) the physical = 2) the cognitive = 3) the emotional < 4) the spiritual.

It is important to guard against sacrificing development in some domains in order to excel in other domains; when such is done, the result is imbalanced people.

 

Although not everyone will be a chemist, I want ours to be a literate and well educated society in which everyone has a helpful understanding of chemistry. I’d also like ours to be a progressive society in which one generation makes it easier for the next to progress.

 

Because of the separation of church and state, teachers in public institutions do not address the spiritual; however, teachers must cultivate student development in the physical, cognitive and emotional domains.  If it is taught well, most undergraduate chemistry students have the ability to flourish at Benjamin Bloom’s knowledge, comprehension, application and analysis levels.

 

 Vision:

Students will emerge from this course with

a) Critical thinking skills that allow them to confidently assess, develop approaches to, and solve unfamiliar and familiar problems

b) A sense of belonging and community at PGCC and in society

c) Motivation to higher educational achievement (derived from successful experiences in my course)

 

 Mission:

Students will engage in hands-on/active/discovery and real learning problem solving experiences, many of which involve collaboration with their peers.

 

Goals and objectives:

Goal 1:  Develop Critical Thinking Skills

Critical Thinking objectives:

 Pertaining to a problem, students will

a) Employ hands-on active learning and discovery exercises involving real models* that are familiar parts of their life’s experience, to solve problems and subsequently

            b) Construct their own knowledge/ arrive at their own conclusions

c) Gather/research already known facts/information/data pertaining to a problem

            d) Define/describe/label/list/outline/state known terms/facts/methods/procedures/concepts and principles associated with the problem

           

e) Break problems/questions/situations down into component smaller problems/questions/situations

f) Generate/devise/formulate/design/organize/create and carry out schemes/experiments/approaches/methods/procedures/tasks for generating data/gathering information needed to solve problems/answer questions/assess situations

 

            g) Compile/organize/categorize/outline gathered data/information/facts and

            h) Analyze it by diagramming/ comparing/relating/differentiating/contrasting/discriminating/separating/sub-dividing it in order to

            i) Discover/recognize/identify/interpret patterns/relationships among narrative/listed/charted/graphed data/facts/information, then

j) Draw mental/narrative/verbal conclusions:  formulate or develop generalizations/rules/principles/methods/procedures and/or

            k) Convert/translate them into mathematical formulas (and vice versa)

            l) Evaluate/test conclusions/ generalizations/rules/principles/methods/procedures and mathematical formulas

            m) Use valid conclusions/ generalizations/rules/principles/methods/procedures and mathematical formulas to

n) Compute/calculate/determine/demonstrate/predict outcomes in familiar and unfamiliar situations

 

Goal 2: Develop a Sense of Community

            Objectives:      

During and as a result of collaborative work, students will

a) Obtain a sense of community/belonging/connectedness with lab and/or activity partners subsequently/ultimately this will

b) Promote their sense of community/belonging/connectedness at the college

                        c) Value collaborative exchange/brainstorming

            d) Bounce their perceptions and ideas off of others without fear of being ridiculed

 

Goal 3:  Motivation

            Objectives:

            Students will

a) Have repeated successful experiences solving challenging problems.

b) Acquire confidence from their successes.

c) Take on other challenging courses with confidence in their acquired problem solving skills

 

* Real learning activities incorporate familiar models (models that are a part of each student’s life’s experience), as in the teaching of concepts.