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This packet contains the course syllabus, chapter objectives and terms, study suggestions, and guidelines for writing the laboratory notebook. Please bring this with you to each class meeting.
Table of Contents
Course Syllabus . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2 Study Suggestions for Organic Chemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8 Guidelines for Writing the Laboratory Notebook . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9 Chapter 15: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15 Chapter 16: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17 Chapter 12: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 19 Chapter 13: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21 Chapter 17: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23 Chapter 18: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 25 Chapter 19: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 27 Chapter 20: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 29 Chapter 21: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30 Chapter 22: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 32 Chapter 23: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 34 Chapter 24: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35 Chapter 25: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 37 Chapter 26: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39 Chapter 27: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41 Chapter 28: Objectives and Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43 JOHNSON COUNTY COMMUNITY COLLEGE COURSE SYLLABUS Organic Chemistry II: CHEM 221
INSTRUCTOR INFORMATION:
Refer to the Instructor Information Sheet distributed at the first class meeting COURSE INFORMATION:
Credit Hours: 5
Contact Hours: 9
Lecture: 3
Prerequisites: CHEM 220
Required
John McMurry, Organic Chemistry, 4th ed., Brooks/Cole (1996).
Textbooks:
D. L. Pavia, G. M. Lampman, G. S. Kriz, and R. G. Engel,
Introduction To Organic Laboratory Techniques, A Microscale
Approach, 2nd ed., Saunders (1995).
Supplies: Safety goggles and lab coats required for laboratory.
Description:
Organic Chemistry II is a continuation of Organic Chemistry I, the nomenclature, principles and theories of organic chemistry with emphasis on electronic theories and reaction mechanisms. Laboratory issupportive in nature with emphasis on developing laboratory techniques and preparation of representativecompounds. Organic Chemistry II completes the study of organic chemistry designed to prepare the studentfor continued work in chemistry and related fields.
Objectives:
After completing this course, the student should be able to: 1. Develop an understanding of organic chemistry which will be useful in the studies of chemistry and related fields such as medicine, engineering, nursing and pharmacy.
2. Use the IUPAC system of nomenclature and parts of the common naming system.
3. Interpret reactions using appropriate mechanisms.
4. Interpret infrared spectra, mass spectra, and nuclear magnetic resonance spectra as a result of lecture and/or laboratory study. The student's ability will be demonstrated by the identification of unknownstructures with the use of spectra.
5. Write chemical reactions as demonstrated by the use of synthesis problems.
COURSE REQUIREMENTS, EVALUATION and GRADING SCALE:
1. EXAMS: A comprehensive final exam will be required. In addition, four hour exams will be given
2. QUIZZES/HOMEWORK: There will be 6 - 12 short quizzes given during the semester. Homework
may be assigned and graded. The quiz and/or homework grades will be combined and weighted so thatthey are worth the same as a hour exam.
3. LABORATORY: A bound laboratory notebook will be kept by each student and evaluated with
respect to completeness, organization, quality of results, and writing style.
4. EVALUATION METHOD: The semester grade will be determined as shown below:
Grading Scale:
TESTING POLICY:
1. Students are required to take all exams on the day, at the time, and in the room in which they are scheduled. Arrangements must be made with your instructor to take an examination early if you haveprior knowledge of a valid excused absence.
2. Makeup examinations may be taken until the exam has been returned to any of the classes. In case of a holiday immediately following an exam day, a makeup exam may not be possible.
3. The student is responsible for notifying the instructor if he or she missed an exam. The instructor will determine whether or not the student is eligible for a makeup exam.
4. If a student is unable to take an exam at the regularly scheduled time for reasons justifiable to the instructor, the section of the final exam corresponding to the missed exam will be used to determine thegrade for the missed exam.
a. The student is only allowed one make-up exam a semester.
b. NO EXAM SCORES WILL BE DROPPED. Once an exam has been taken, the score on that exam stands as the earned score. Scores from the final will not replace unit exam scores.
ATTENDANCE POLICY:
Regular class attendance is essential to doing well in this course. It is important that you keep absences to a minimum. The student is responsible for getting materials and notes for a missed lecture from aclassmate.
WITHDRAWAL DATE: The last day to withdraw from a class with a "W" is April 15.
ACADEMIC DISHONESTY POLICY:
Academic dishonesty will not be tolerated and will be dealt with severely. All persons that knowingly participate in dishonest behavior are equally guilty and may be dealt with in the same manner. In additionto zero scores on the assignments, papers, and tests, the student(s) can be dismissed from class, the college,and/or prosecuted.
DISABILITIES IDENTIFICATION:
If you are a student with a disability, and if you will be requesting accommodations, it is your responsibility to contact Special Services. Special Services will recommend any appropriateaccommodations to your instructor and his/her director. The instructor and director will identify for youwhich accommodations will be arranged.
COMPUTER AIDED INSTRUCTION:
To assist you in learning some basic concepts of organic chemistry, there are number of computer-aided instructional programs available for student use in the CASE classroom, CLB 112.
These programs do not require any prior computer knowledge (a lab monitor will be on hand to assist
you should you need help). Some of the programs you may use are listed below:
GENERAL COMMENTS:
Organic chemistry is a difficult subject for many people. To a great extent it must be self-taught. It requires a lot of listening, reading, studying, and problem solving. As you read the text, work through the
examples as you read. Coming to class, listening and actively taking notes will also help you learn the
concepts and reactions of organic chemistry. To succeed in this course, the student must take the
responsibility to learn the material through hard work and practice.
As you study, strive to understand the causes of chemical change as opposed to memorizing as many reactions as you can. In most cases, an understanding of the reaction mechanism will allow you to predict
the outcome of a given reaction. To test your understanding of a given topic, you should attempt to do as
many problems from the textbook as possible. Homework problems should be approached as tests.
Work each problem on your own before consulting the study guide.
This course will be time consuming. You should plan to spend a minimum of 2 hours of outside work
for each hour of lecture. In addition, you should spend a minimum of 1-2 hours preparing for each
laboratory experiment (carefully reading the experiment and preparing your notebook). To be successful
in this course, you must arrange your schedule to find this time.
Finally, please use your instructor as a resource. One major benefit of attending J.C.C.C. is the opportunity of working directly with your instructors. Feel free to drop by during my office hours for extrahelp or to voice concerns regarding the course. If my office hours do not fit your schedule, you may makean appointment with me for additional help.
EVALUATION OBJECTIVES:
Factual knowledgeProfessional skills and viewpointsThinking and problem solvingPrinciples and theories CAVEATS:
The schedule and procedures for this course are subject to change in the event of extenuatingcircumstances.
Students entering physical science classes should be aware that they may be in close contact withpotentially hazardous chemicals and equipment. The student must assume responsibility in conductingthemselves in a manner to minimize such hazards.
Chemical hazards dictate that goggles, shoes and protective covering (lab coats or approved substitute)will be worn whenever chemicals are used in the laboratory. Students will not be allowed to performlaboratory experiments without proper attire and lab coats (shorts and sandals will not be allowed). Inthe laboratory, consumption of food, beverages or tobacco is strictly prohibited and will not be tolerated.
Unauthorized experiments are prohibited. Students will not be allowed in the laboratory unless aninstructor is present at all times.
Lecture Schedule: Spring 1997
Chapter No.
Chemistry of Benzene: Electrophilic Aromatic Substitution Chemistry of Benzene: Electrophilic Aromatic Substitution E.A.S. of Arylamines. The Sandmeyer Reaction Exam #1: Chapters 15 and 16, IR spectroscopy and Mass Spectrometry Aldehydes and Ketones: Nucleophilic Addition Reactions Aldehydes and Ketones: Nucleophilic Addition Reactions Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Amino Acids and Proteins (time permitting) During the week of May 12-15 (see the JCCC Spring 1997 Credit Class Schedule for thetime and date for your section) Caveat: The schedule above is subject to change in the event of extenuating circumstances.
Laboratory and Examination Schedule: Organic Chemistry II
Experiment No.
Assigned Questions
Introduction to Mass Spectrometry (lecture and CASE) Exp. 34: Relative Reactivities of Aromatic Compounds ( EXAM #1: Chapters 15-16 and sections 26.2-26.3
Instrument Lab: NMR (meet in CASE classroom) Exp. 60: Isolation of Essential Oils (IR and NMR) Exp. 25: Triphenylmethanol and Benzoic Acid Exp. 24: Chromic Acid Oxidation of Alcohols ( EXAM #2: Chapters 17-19
Exp. 26: Coenzyme Syn. (save product for Exp. 27) ( Exp. 27: Benzil (save product for Dilantin expt.) ( Exp. 51: Esterification Reactions of Vanillin (NMR) EXAM #3: Chapters 20-23
Exp. 31: Enamine Reactions: 2-Acetylcyclohexanone Organic Qualitative Analysis (meet in the CASE classroom) EXAM #4: Chapters 24-27
( indicates that the experiment may be written up as "short report" (see lab notebook guidelines) Caveat: The schedule above is subject to change in the event of extenuating circumstances.
Study Suggestions for Organic Chemistry
1. Lecture: Come to every class meeting and take careful notes. To get the most out of lecture, you
should read the assigned materials before coming to class. Some students like to recopy their lecture
notes after class; this can be an effective tool if is done actively. Think about the material as you are
recopying; use the text to fill in any gaps in your lecture notes.
2. Reading the textbook: Chemistry is not a spectator sport. Reading the text should be done actively
with pencil and paper. Write out chemical reactions presented in the text, draw the structures, and usemolecular models. Mark anything that is confusing. Reread the assigned material after the lectures.
Work the sample problems and the problems within the chapter before beginning homework assignments.
3. Homework: Approach the homework assignments as tests. Try to work each problem on your own
before consulting the study guide. Do not simply copy the answers out of the study guide! To learnthe material you must actively engage your mind in recall and problem solving.
4. Molecular Models: Make frequent use of molecular models. The models will help you relate the two
dimensional, pencil-and-paper drawing of a structure to the true (three dimensional) molecular structure.
Proper 3-D visualization of molecular structure is essential in the study of stereochemistry. Severalmodel sets are on reserve in the library.
5. Study groups: Get together with two or three of your classmates on a regular basis to go over course
material and solve problems. Don't waste your time or the time of other group members: read theassigned material and attempt the problems before meeting with the group.
6. Chemical Reactions: One of the objectives of this course is to be able to predict the outcome of a
number of organic chemical reactions. In most cases, our analysis of a chemical reaction will be based
on a knowledge of the reaction mechanism. The following information should be noted about each
major type of reaction studied:
a. Name (class) of reaction.
b. General example of the reaction (use R groups) including all necessary reagents, solvents
c. Specific example(s); include cyclic cases where possible.
d. Step-by-step mechanism showing electron movement with small curved arrows.
e. Stereochemistry and regiochemistry of the reaction.
f.
Structural effects on the reaction.
Write down this information on a separate sheet of paper for each type of reaction studied (some peopleprefer to use large note cards to store this information for use as flash cards).
7. Exams: The exams will test your ability to recall factual information and to apply your knowledge and
understanding to new situations. Do not wait until the night before an exam to begin studying thematerial! It is important to develop an understanding of the material as opposed to memorizing as muchas you can.
Organic Chemistry Laboratory
Guidelines for Writing the Laboratory Notebook
General Information:
Each student is required to keep a bound (not spiral or loose-leaf) laboratory notebook that will be collected and graded at various times during the semester. For each experiment you will prepare a written
report. These reports do not need to be lengthy. Your aim should be to write reports that are both concise
and complete; do not "pad" your reports with unnecessary information. In addition to the following
guidelines, be sure to read pp. 22-29 in your lab text (Pavia, Lampman, Kriz, and Engel, Introduction to
Organic Laboratory Techniques, 2nd.ed.) and follow those suggestions as well.
Before Lab:
Advance preparation is very important in organic chemistry for the prevention of accidents and to promote understanding. Read the safety information in the lab text (pp. 5-21 in Pavia, et al.). Be aware
of potential chemical hazards that you may encounter as outlined in the experiment and those noted by the
instructor. "Cookbook" chemistry will not be tolerated. Sections 1-5 (and parts of 6) of the lab report are
to be done before lab; failure to prepare the notebook can result in a "point" deduction for that experiment
(!25% for that lab). Students will not be allowed to work in the laboratory without a properly
prepared notebook.
Notebook Format:
Leave a few blank pages at the beginning of the notebook for a Table of Contents and keep it up to date.
Number the pages of your notebook in the upper right-hand corner of each page. Use an ink pen
exclusively for writing in the notebook and record all observations and experimental data directly in
your notebook as you are doing the experiment. If you make a mistake, draw a single line through the
suspect entry. Do not erase or obliterate the entry. Some of the experiments will be selected by the
instructor to be written up in the "short report" format (see the list on page 14), but the majority of the labs
are to be written in the "long report" format described below:
L Each long report must contain the following 8 sections in the following order: 1. Experiment Number, Title of Experiment, Reference, Date, and Lab Partners Name. Ordinarily,
the reference will be your lab text. If the reference is a handout, attach the handout to your report.
2. Purpose. Provide a short statement of the purpose(s) of the experiment in your own words. Often the
experiments have more than one purpose.
3. Chemical Reaction(s). Use structural formulas to write balanced chemical equations for the main
chemical reaction(s). Do not write mechanisms here. Write the reaction conditions (solvent,
temperature, catalysts, etc.) over the arrows. Then calculate the theoretical yield of the desired product
in millimoles and milligrams (or grams). Clearly identify the limiting reagent.
CH CH CH CH OH + Br )))))))< CH CH CH CH Br + OH Theoretical yield: In the example above, 7.65 mmoles of CH CH CH CH Br can be formed, so,
Some experiments do not call for the preparation of a compound. In those cases, you can skip to thenext section.
4. Separation Scheme: Separation (purification) schemes are discussed in p. 24 of the Pavia lab text.
Show, by means of a flow chart, how the desired product is to be separated from the reaction mixture
(i.e. solvents, excess starting materials, and unwanted side products). Be specific, but not overly
detailed - see the example at the end of these guidelines (note: separation schemes are not required
for "short reports").
5. Procedure: Write a concise version of the experimental procedure in your lab book. Do not copy
verbatim from the text. Include sketches of any apparatus that is being used for the first time. Do notspend too much time here. Keep it as short and simple as possible.
During the experiment: write down any relevant observations that you make and any changes to thepublished material. 6. Data: Record all data directly in the notebook in tables or on labeled, underlined blanks
Prepare a two-column Data Table that includes those physical properties of the major reactants and
products that are relevant to the experiment (e.g., molar mass, mp or bp, density, or index of
refraction). Leave blank spaces to record the actual yield (in grams or milligrams) and the percent
yield of the desired product(s). Clearly show how you calculated the percent yield.
Prepare the table of literature values before class.
Neatly attach any graphs or spectra that you obtain to your notebook as part of this section.
7. Conclusions: Refer to the discussion on the next page.
8. Questions: Answer the assigned questions (check the lab schedule for specific question numbers) at
Conclusions:
Write a brief, coherent conclusion that focuses on the chemical and physical principles involved in the experiment. Think of the purpose(s) of the experiment; was the experiment a success? Provide a briefexplanation for any disagreement between your results and the accepted (i.e., literature) values. In someexperiments, you may want to suggest ways the procedure could be improved.
This is the one area of the report that you should strive to write in complete, grammatically
correct sentences. Make a rough draft on scratch paper and then copy a revised version into your
notebook. It is probably best to do the questions first, they will often give you ideas for the conclusion.
Consult your lecture textbook or other references for additional information as needed.
Example: (Experiment 1: Isolation of the Active Ingredient of an Analgesic Drug)
The following is an example of a poorly written conclusion.
"Basically, you could say the expt. was a sucess. Our melting point was 115EC. This wasn't real good but that wasn't my fault because we had to rush thru the experimet and couldn't find all our suplies at first.
But I did learn lots of good lab techniques that we can use again." L Worse than the obvious misspellings and rambling nature of the comments above, is the fact that nothing of substance was mentioned. For example, the experimental melting point was mentioned, butno comparison was made to accepted values - only a vague statement was made about the quality of theresult ("This wasn't real good but.").
The following is an example of a well-written conclusion.
"In this experiment, we isolated acetylsalicylic acid, ASA (the active ingredient in aspirin), from a commercially prepared aspirin tablet. The ASA was extracted from the crushed aspirin tablet withmethanol. The methanol solution was filtered to remove insoluble impurities and then most of the methanolwas evaporated in the hood. After cooling the remaining solution, the ASA crystallized from the solutionand the solid ASA was collected by vacuum filtration. The percent recovery of acetylsalicylic acid from theaspirin tablet was low (42.6%). This low yield may be a result of a combination of factors: Decompositionof the product in methanol, transfer losses in the vacuum filtration step, and retention of some product onthe alumina column. In addition, some of the acetylsalicylic acid may not have dissolved in the methanolused in the initial extraction. Our experimental melting point of 123 - 127EC was about 11E lower than the accepted value of 135 - 137EC stated in the laboratory textbook. This low value, coupled with the fact that the product melted overa relatively wide range of temperatures, suggests that our product was contaminated with impurities (e.g.,unreacted salicylic acid or other decomposition products). The presence of dissolved impurities in a solid(solvent) lowers the melting point relative to that of the pure solid. This phenomenon is known as freezingpoint depression. To a first approximation, the extent to which the freezing point is lowered depends onlyon the number (concentration) of dissolved impurities (solute) and not their specific chemical properties1." References
1.
S. Zumdahl, Chapter 11 in Chemistry, 3rd. ed., D.C. Heath, Lexington, MA. (1993).
L Note that the second conclusion is not too long - only two paragraphs were written. The discussion in the first paragraph about the low percent recovery was prompted by answering question #1 at the endof the Exp. #1. In paragraph number two, the idea to discuss freezing point depression came fromreading the background information about Exp. 1 in your lab book. Notice the use of a freshmanchemistry text as an additional reference in the discussion of freezing point depression.
Sample Separation Scheme for Experiment #2
A separation scheme uses a "flow chart" to show how the desired product is to be separated from the reaction mixture (i.e., solvents, excess starting materials, and unwanted side products). The separationscheme should be detailed, but it should not include each step of the experimental procedure. Note: the separation scheme starts "after" the reaction has been completed.
Grading:
The lab reports will be collected and graded at various times in the semester as decided by your instructor. The books will be graded on either a "point" or a "percentage basis" (consult your instructor for
details). Extensive corrections will not be made in each lab book. Mistakes and omissions will be
marked in your lab book and a score will be assigned to your lab book in each of the four broad categories
listed below.
Your laboratory grade will be determined largely from your laboratory notebook and your laboratory technique. You should strive to obtain good results in lab, but, in general, you will not be unduly penalizedfor low yields and poor results early in the semester.
Report the results that you obtained, not the results that you thought you should have obtained.
Keep in mind that a poorly organized, overly sloppy, or incomplete report will receive a lower grade than an "equivalent" notebook that is well organized, neat, and complete. The ability to write clear andeffective technical reports is one of the most important goals of this laboratory class. Sloppy andincomplete work is not acceptable in an industrial, clinical, or business setting, and it is not acceptable here.
Each lab exercise and report will be evaluated in each of the following categories: *Breakdown of Prelab category (30% of overall score) 3. Chemical Reaction and Theoretical Yield Writing Center:
A sample laboratory report is available for you to examine in the J.C.C.C. Writing Center, EMC 308.
You are encouraged to make use of the writing center. If the conclusion section of your lab report is poorlywritten, your instructor may require that you go to the writing center and get help in making the necessarycorrections. If you are sent to the writing center, you must get your lab book initialized by a writing centertutor.
Repeating an Experiment:
Early in the semester, if you have an experiment that fails due to some blunder, you might be allowed to repeat the experiment, with only a minor point deduction (!10%). A common pitfall early in the organiclab is "throwing out the wrong layer." Do not carelessly discard a layer in an extraction process, test it tosee if it is "organic" or "aqueous" before disposing of it.
"Repeat experiments" are completely at the discretion of the instructor. If your instructor agrees
to let you repeat an experiment it must be done in the next lab period while you are working on the nextexperiment.
As the semester progresses, you will be expected to show improvement in your laboratory technique.
By midsemester, no experiments will be repeated. At that point, the instructor will provide you with somedata from another group so that you can complete your report. The penalty for mid- to late-semesterblunders is !20% for that lab.
Short Reports:
In the "short reports," a separation scheme is not required. The conclusion section of a short report should be brief and to the point. The conclusion should be limited to a concise analysis of your resultsincluding spectral interpretation (if IR or NMR spectra were obtained). This semester, the followingexperiments are to be written up as "short reports:" Relative Reactivities of Several Aromatic Compounds Carbohydrates (use the data tables provided by the instructor; do not write up aprocedure) You are still required to answer the assigned questions (see the lab schedule for a list) for the short reports.
Upon completion of this chapter the student should be capable of the following tasks: 2. Name (by IUPAC) and draw structures for aromatic compounds. Know the names and structures for: toluene, phenol, aniline, acetophenone, benzaldehyde, and benzoic acid.
3. Explain how Kekulé accounted for the unusual properties of benzene.
4. Compare the reactivity of benzene to cyclohexene.
5. Use thermodynamic data to show that benzene is more stable than the hypothetical compound 1,3,5- 6. List the four postulates of resonance theory.
7. Use Hückel's rule to determine if a given compound is aromatic.
8. Use M.O. theory to describe the bonding in benzene and other aromatic compounds.
9. Describe the bonding in polycyclic aromatic hydrocarbons.
Work the following problems: 1-5, 8, 9, 10(resonance only), 11-20, 22, 24, 32, 33,37, 40, 46.
! The following problems involve 1H NMR spectroscopy, and should be done at the appropriate Upon completion of this chapter the student should be capable of the following tasks: 2. Draw and explain the general mechanism for electrophilic aromatic substitution.
3. Predict the products and/or write mechanisms for the following types of electrophilic aromatic a. halogenationb. nitrationc. sulfonationd. Friedel-Crafts Alkylatione. Friedel-Crafts Acylation 4. Explain how substituents affect the reactivity of an aromatic ring 5. Discuss ortho-para and meta directors and give some characteristics and examples of each.
6. Predict the orientation of incoming groups in disubstituted benzene rings.
7. Recognize the conditions necessary for nucleophilic aromatic substitution to occur. 8. Draw and explain the addition-elimination mechanism and the elimination-addition mechanism in nucleophilic aromatic substitution reactions.
9. Compare and contrast the way the ring and the side-chain react.
Read sections 25.2 - 25.3, "Preparation and Reactions of Arylamines" (pp. 977-985).
b. Be familiar with the replacement reactions of arenediazonium salts.
c. Show how diazonium salts can be used in coupling reactions.
Use the reactions learned in the chapter to work synthesis problems.
Work the following problems: 1, 3-16, 18-31, 41, 43, 45, 47, 48, 50, 51, 57, 58, 65,67.
work the following problems from chapter 25: 3-5, 7, 9, 11, 18a, 27a, 34 ! This chapter is assigned as a reading chapter to provide a theoretical background for the use of mass spectroscopy and infrared spectroscopy in organic chemistry. Sections 12.4 - 12.8 should beconsidered as review (infrared spectroscopy was covered in Organic Chemistry I). Make sure thatyou can do the assigned problems. Emphasis will be placed on spectral interpretation.
Upon completion of this chapter the student should be capable of the following tasks: 2. Write molecular formulas corresponding to a given molecular ion.
3. Use mass spectra to determine molecular weights and base peaks, and to distinguish between 4. Be familiar with the regions of the electromagnetic spectrum used in organic spectroscopy.
5. Know how energy, frequency, and wavelength are related for electromagnetic radiation.
6. Know what type of molecular absorptions give rise to IR spectra.
7. Interpret IR spectra of organic compounds.
8. Work the following IR problems: 6-13, 26-34, 36-39.
9. Work the following MS problems: 1, 4, 5, 19, 20, 22, (23b) , 24, 42, 43 L The following tutorial programs are available in the CASE classroom: Introduction to Mass Spectroscopy (Clough)Introduction to IR Spectroscopy (Clough)IR Tutor (Abrams) ! This chapter is assigned as a reading chapter to provide a theoretical background for the use of nuclear magnetic resonance spectroscopy in organic chemistry. NMR spectroscopy will beintroduced in the laboratory portion of the course. Emphasis will be placed on interpretation of 1HNMR spectra.
Upon completion of this chapter the student should be capable of the following tasks: 3. Understand basic NMR concepts (e.g., shielding and deshielding, chemical shifts, spin-spin 4. Interpret first-order 1H NMR spectra (chemical shifts and splitting patterns) of organic compounds.
5. Describe the advantages of 13C NMR spectroscopy over 1H NMR spectroscopy.
6. Interpret broadband decoupled 13C NMR spectra.
7. Work the following H NMR problems: 1-4, 7-13, 15, 33-35, 39-42, 44, 48 8. Work the following C NMR problems: 16-18, 46, 47 Upon completion of this chapter the student should be capable of the following tasks: 2. Name (by IUPAC) and draw structures for alcohols.
3. Compare the physical properties of alcohols to alkanes and alkyl halides.
4. Show how to use acid-base reactions to prepare alkoxide ions.
5. Show how alcohols are prepared from alkenes, aldehydes, ketones, esters, and carboxylic acids.
6. Show how the Grignard reaction can be used to make 1E, 2E, or 3E alcohols.
7. List the limitations on the use of the Grignard reaction.
8. Show how alkenes, alkyl halides, and tosylates can be prepared from alcohols.
9. Show how alcohols may be oxidized to carbonyl compounds.
Discuss the use of protecting groups in organic synthesis.
Work the following problems: 1-14, 16, 17, 20-26, 29, 30(a,c,e), 31, 33, 34, 37, 39,40, 45(b,c), 46.
protecting group (use TMS ether as an example) Upon completion of this chapter the student should be capable of the following tasks: 2. Name (by IUPAC) and draw structures for ethers.
3. Compare the physical properties of ethers to alkanes of comparable molecular weights.
4. Show two methods for preparing ethers.
5. Predict the products formed in an acid-induced cleavage of an ether.
7. Show the mechanism and predict the product formed (with correct stereochemistry) in the acid- catalyzed and base-catalyzed ring opening reactions of epoxides.
8. Discuss the use of crown ethers in organic synthesis.
9. Work the following problems: 1-5, 7-14, 19, 20, 22, 24(a,c,e), 26, 27, 30, 48(a,b) ! To master the material from this chapter, the student should understand and be able to apply the nucleophilic addition mechanism to a number of different reactions. Do not attempt to justmemorize the reactions without understanding the mechanism.
Upon completion of this chapter the student should be capable of the following tasks: 2. Name (by IUPAC) and draw structures for aldehydes and ketones. Be familiar with the following common names: formaldehyde, acetaldehyde, benzaldehyde, acetone, acetophenone, benzophenone.
3. Compare the physical properties of aldehydes and ketones to alkanes and alcohols of comparable 4. Show by equations at least three methods for preparing aldehydes and at least five for preparing 5. Show the general mechanism for nucleophilic addition at the carbonyl group.
6. Show by equation the addition of water or alcohols to the carbonyl group.
7. Show by equation the reaction of HCN with carbonyl groups.
8. Compare and contrast the reactions of aldehydes and ketones with oxidizing and reducing agents.
9. Show by equation how ammonia and its derivatives add to the carbonyl group.
Show a mechanism for the Wittig reaction.
Know the types of reagents and conditions required for addition to ",$-unsaturated carbonyls.
Work the following problems: 1-9, 11, 12, 14, 15, 20(list C=O peaks only), 21,23(evens), 24-28, 30-32, 34, 37, 39, 40(skip a,c), 41, 42, 45, 52, 53, 57 Upon completion of this chapter the student should be capable of the following tasks: 2. Name (by IUPAC) and draw structures for both mono and dicarboxylic acids. Be familiar with the following common names: formic acid, acetic acid, benzoic acid, oxalic acid.
3. Discuss the physical properties of carboxylic acids.
4. Discuss the acidity of carboxylic acids and the factors that affect the stability of carboxylate anions.
5. Discuss substituent effects on acidity.
6. Explain the acidity of phenols in terms of their structures (see chapter 25).
7. Be able to demonstrate various methods of preparing acids.
8. List and discuss four types of general reactions of carboxylic acids.
9. Show by equation how carboxylic acids are reduced to primary alcohols.
10. Work the following problems: 1-17, 19-25, 27, 30-34, 40, 43 ! To master the material from this chapter, the student should understand and be able to apply the nucleophilic acyl substitution mechanism to a number of different reactions. Do not attempt to justmemorize the reactions without understanding the mechanism.
Upon completion of this chapter the student should be capable of the following tasks: 2. Name (by IUPAC) and draw structures for acid halides, acid anhydrides, amides, esters, and nitriles. Be familiar with the following common names: acetyl chloride, acetic anhydride, acetamide, andacetonitrile.
3. Show the general mechanism for nucleophilic acyl substitution.
4. Be familiar with the common chemical reactions of the acid derivatives that occur by the nucleo- 5. Be able to draw and explain the following mechanisms: a. hydrolysis of acid halides.
b. acid-catalyzed esterification.
c. acid-catalyzed hydrolysis of esters.
d. base-induced hydrolysis of esters.
e. acidic hydrolysis of amides and nitriles.
6. Become familiar with the summary of reactions at the end of the chapter.
7. Work the following problems: 1-8, 11, 15-18, 20-22, 24-26, 30-33, 37, 38, 40, 42, Upon completion of this chapter the student should be capable of the following tasks: 2. Distinguish between tautomerism and resonance 3. Show the general mechanism for an alpha substitution reaction via an enol or enolate ion intermedi- 4. Show by equation the alpha halogenation of aldehydes and ketones.
5. Be familiar with the HVZ reaction.
6. Be familiar with the haloform reaction.
7. Be familiar with the malonic ester and acetoacetic ester syntheses.
8. Work the following problems: 1-6, 8-25, 28, 30, 32, 42, 44, 46 Upon completion of this chapter the student should be capable of the following tasks: In this chapter, emphasis will be placed on the aldol condensation reaction. The following carbonylcondensations may be covered to a lesser extent: a. Claisen reactionb. Dieckmann cyclizationc. Michael reactiond. Enamine reactione. Robinson annulation reaction 2. Show the general mechanism for a carbonyl condensation reaction.
3. Explain the aldol reaction using mechanisms as necessary.
4. Recognize the conditions under which aldol condensation (dehydration) occurs.
5. Use the aldol reaction in synthesis problems.
6. Work the following problems: 1-9, 11, 15, 24-29, 33 Upon completion of this chapter the student should be capable of the following tasks: 2. Name (by IUPAC) and draw structures for amines.
3. Discuss the physical properties of amines.
4. Discuss the basicity of amines in terms of their structure.
5. Compare the basicity of amines to amides.
6. Explain how an optically active amine can be used to resolve a racemic mixture.
7. Show methods for the preparation of amines.
Work the following problems: 1-9, 11-13, 16, 17, 19-25, 28, 31, 33, 35, 52.
Upon completion of this chapter the student should be capable of the following tasks: 2. Explain why alkyl amines are more basic than arylamines.
4. Be familiar with the replacement reactions of arenediazonium salts.
5. Show how diazonium salts can be used in coupling reactions.
6. Explain the acidity of phenols in terms of their structures.
7. Show two methods for the preparation of phenols.
8. Be familiar with the reactions of phenols listed in the chapter summary.
9. Work the following problems: 1-2, 12-14, 16-20, 24-26, 27b, 39, 44.
(problems 3-5, 7, 9, 11, 18a, 27a, 34 were assigned for UNIT I) Upon completion of this chapter the student should be capable of the following tasks: 2. Know how to classify carbohydrates by the number of carbons, presence and size of ring, type of 3. Explain how the (R)/(S) and D/L systems of nomenclature are alike and how the are different. Give some advantages and disadvantages of each.
4. Draw monosaccharides in the following representations and be able to convert from one representa- tion to another:a. Fischer projectionb. Haworth projectionc. Chair conformations 6. Explain why some sugars are reducing and why some are not.
7. Discuss the effect of various oxidizing agents (e.g., Br /H O, HNO , Tollens, Benedict's, and Fehling's solutions) on monosaccharides.
8. Discuss the importance of the Fischer-Kiliani synthesis and the Wohl degradation.
9. Explain (but don't memorize) the Fischer proof of the stereochemistry of glucose.
Discuss the similarities and differences between starches and cellulose.
Work the following problems: 1-6, 9-11, 13-14, 16-24, 26-35, 55, 56(a,b).
! This material may be covered on the UNIT IV exam (TIME PERMITTING) Upon completion of this chapter the student should be capable of the following tasks: 2. Given the structural formula for an amino acid, be able to classify it as an ionic (acidic or basic) or neutral (polar or nonpolar) amino acid.
3. Given the structural formula for an amino acid, be able to draw it with correct stereochemistry (as a Fischer projection) and draw the dipolar form.
4. Understand the acid-base behavior of amino acids.
5. Show several methods of preparing amino acids in the laboratory.
6. Draw the structures of simple peptides.
7. Compare and contrast primary, secondary, tertiary and quaternary structures of proteins.
8. Work the following problems: 3 - 9, (10-11), 15, 16, 28, 30, 32-34, 43a, 48, 53, 60, ! This material may be covered on the UNIT IV exam (TIME PERMITTING) Upon completion of this chapter the student should be capable of the following tasks: 2. Draw the structures of fats and oils.
3. Locate the isoprene units in a terpene.
4. Draw chair conformations of steroids from a planar representation.
5. Work the following problems: 1-5, 7, 8, 17, 26-30.

Source: http://staff.jccc.net/franklin/org2book.pdf