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Reading Assignments:
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- Readings and objectives will get perturbed forward or back often because it is more important to me that we reach understanding of a topic than it is that we cover material just to be covering it. Therefore rather than putting dates on this table I will move a rose colored marker down the table as we finish each topic. You should be reading the topic after the rose colored marker. The problems associated with the readings are indicated. The problem due at the beginning of class on the following day will be indicated in class
Reading Assignments, Objectives, and Daily Problems
| Readings |
Objective. (In each case these start with "Be able to". The rose colored (well, it WOULD make a good color for a rose) indicator shows you where we are in class.) |
Daily Problems Due |
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Part I. Preliminaries |
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| 1-20 |
Review:
give electronic configuration of Li through F and Na through Cl.
know the number of valence electrons in each of those elements.
determine polarity in bonds.
draw simple Lewis structures. |
1-4 |
| 82-84 |
recognize ketones, aldehydes, acyl compounds, alkenes, and alkynes.
give the structure around carbon atoms using VSEPR.
draw skeletal structures. |
5-7 |
| 21-44 |
draw angular view of atomic orbitals.
determine constructive and destructive overlap between atomic orbitals.
determine the direction that hybrid orbitals point.
determine the hybridization used by a carbon atom in a given structure. |
8-13 |
| 71-82; 790-793; 85-91 |
name alkanes, ketones, aldehydes, alcohols, and compounds with other functional groups |
15-18 |
| 124-136 |
calculate ihd for various compounds.
name alkenes. |
19-21 |
| 101-106 |
draw and use Newman projections. |
22-24 |
mid 800-mid 801
796-797 |
use epwa to describe the reactions of BH4- with an aldehyde or ketone.
use epwa to describe the reaction of a Grignard reagent with an aldehyde or ketone.
devise a synthesis of an alcohol. |
25-32 |
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Part II. Spectroscopy |
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| 528-549 |
identify characteristic stretching vibrations. |
33-35 |
| 569-585 |
describe the basic phenomenon of nmr spectroscopy.
understand and predict chemical shifts.
find hydrogen atoms in the same environment and predict relative areas of nmr signals. |
36-41 |
| 586-602 |
understand the cause of spin-spin splitting.
use simple spin-spin splitting to identify compounds.
make sense of the nmr of compounds where one of the five advanced spin coupling rules hold.
describe circumstances where the spin rule is (a) (n+1)(n'+1), (b) (n+n'+1) or (c) garbage! |
42-45 |
| 610-615 |
use 13C nmr to determine the structure of molecules. |
46-48 |
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Part III. Reactions of Carbonyl Compounds0 |
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| 44-55 |
predict the relative strengths of acids that differ in the atom to which H is attached.
understand the role of hybridization in predicting acidity. |
49 |
| 800 |
use epwa to show the reaction of an alkyne anion with carbonyl compounds. |
50-51 |
287-305
312-315 |
draw resonance structures.
assess when resonance structures are very important and when they play a minor role.
see conjugated systems and appreciate the stability consequence. |
52-56 |
| 822-825 |
describe the mechanism of the Wittig reaction.
synthesize epoxides with sulfur reagents. |
57-58 |
| ---- |
to understand the nucleophilic opening of oxiranes.
to determine the product of the acid catalyzed opening of an oxirane.
use oxiranes in synthesis. |
59-60 |
| ---- |
determine the "carbon level" of a given compound. |
61-62 |
| 445-447 |
write the mechanism for the oxidation of an alcohol. |
63 |
| ---- |
use the reactions we have learned to date to synthesize compounds. |
64-65 |
814-816
805 |
demonstrate the mechanism of hydration of a ketone or aldehyde under acidic conditions.
show base catalyzed formation of a diol from an ketone or aldehyde.
sketch the formation of a cyanohydrin from an aldehyde or ketone. |
66 |
| 816-822 |
show the mechanism of formation of hemiacetals (hemiketals) and acetals (ketals).
use protecting groups for aldehydes and ketones |
67 |
| 806-810 |
use epwa to show the formation of imines and related compounds. |
68 |
| 811-813 |
understand key reactions of imines, hydrazones, and oximes |
69-73 |
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Part IV. Substitution Reactions of Acyl Compounds |
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722-731
660-665 |
name acyl compounds.
guess relative positions of the C=O peak.
understand amide nmr spectra |
74 |
| 733-738 |
appreciate the role of acidity in acyl substitution.
understand the importance of resonance in acidity. |
75-80 |
738-752
757-765 |
write mechanisms for substitution of acyl compounds. |
81-88 |
| 796-804 |
show how carbon level 3 compounds are converted to carbon level 2 or 1 compounds by "C- or H-" compounds. |
89-98 |
| ---- |
know the difference between kinetic and thermodynamic control. |
99-101 |
| 830-834 |
understand reactions of α,β-unsaturated systems. |
102-104 |
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Part V. The Last Pillar: Stereochemistry |
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| 104-110 |
understand the stability of various size ring alkanes.
differentiate between torsional strain and angle strain.
make a careful drawing of the conformer of cyclohexane. |
105 |
| 110-116 |
distinguish between axial and equatorial positions in cyclohexanes.
understand the energy difference between the two conformers of monosubstitued cyclohexanes. |
106-109 |
| 200-205 |
see the "handedness" of certain molecules.
use the concept of a chiral (aymmetric) center to find enantiomers.
use the concept of a plane of symmetry (or center of inversion) to find enantiomers. |
110 |
| 206-211 |
name enantiomers. |
111-112 |
| 212-234 |
appreciate that two enantiomers rotate plane polarized light in different directions.
use the flow chart to determine the type of isomer.
find meso compounds.
find diastereomers. |
113-115 |
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Part VI. Reactions of the C-C π bond. |
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| 124-136 |
use the E,Z nomenclature system for alkenes. |
116-117 |
| 188-192 |
predict the relative stability of various alkenes. |
118-121 |
176-178
242-246 |
use epwa to show the addition of Br2 to an alkene.
account for the stereochemistry of this addition.
extrapolate your knowledge to deal with halohydrin and haloether formation. |
122-125 |
169-172
172-175 |
write the mechanism for the hydration of an alkene.
predict rearrangements of carbocation intermediates. |
126-129 |
| 180-181 |
use oxymercuration/reduction to produce alcohols from alkenes. |
130-132 |
184-188
241 |
show how hydroboration occurs.
use epwa to show the mechanism of oxidation of a trialkylboron compound.
predict the stereochemistry of addition of BH3
use BH3 chemistry to synthesize amines. |
133-136 |
182-184
240 |
prepare epoxides directly from alkenes. |
137-138 |
923-924
926-928 |
determine the product of reaction of an alkene with OsO4.
predict the products of ozonolysis of alkenes with subsequent treatment with either reductive or oxidative reagents. |
141-142 |
| 188-189 |
reduce alkenes to carbon level 0 with H2. |
139-140 |
| 264-274 |
carry out reactions of alkynes. |
143-147 |
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Instructor:
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Robert Linck
Office, Sabin-Reed 429
Phone, X3836
Email, rlinck(at)science.smith.edu
Office Hours, M, 1-3; Tu, 9-11; Fri, 1-2:30; or by appointment
Problem Sessions, M, W, F, 0800-0830; Friday, 2:30 until done.
Laboratory:
Maria Bickar, Coordinator,
Office, Sabin-Reed 335
Phone, X3960
email, mbickar(at)science.smith.edu
Office Hours, TBA
Becky Thomas,
Office, Sabin-Reed 228
Phone, X4422
email, rthomas(at)science.smith.edu
Office Hours, TBA
Smita Jadhav
Office, Sabin-Reed 431
Phone, X3843
email, sjadhav(at)email.smith.edu
Office Hours, TBA
Fagan, Maureen
Office, Sabin-Reed 230
Phone, X3839
email, mfagan(at)email.smith.edu
Office Hours, TBA
Linck, Robert
Office, Sabin-Reed 429
Phone, X3836
email, rlinck(at)science.smith.edu
Office Hours, See above.
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Syllabus:
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- Purpose
Chemistry II: Organic Chemistry, is the second course in the four semester, Chemistry I-IV, sequence; it is a course focused on the structure and reactivity of organic compounds, especially those compounds that contain the "C double bond O" groups in its various forms and the "C double bond C" and "C triple bond C" groups. Our aim will be to explore this chemistry on the basis of a few unifying principles so that we can find order in the chaos. We will be especially concerned with the ability to use the reactions that we learn to synthesize (at least on paper) desired molecules. This chemistry is rich and varied, but the puzzles that are presented in terms of determination of structure, the prediction of reactivity, and the design of synthetic paths are easily approached given a set of rather simple tools. It is the joy of solving such puzzles that makes this course interesting to me; and, I hope, to you.
To get useful information from this course requires practice. It does not matter what your intent is: be it to prepare for MCATs, to give balance to your courses as a English major, or to continue your study of chemistry just "because it is there". The course, "Organic Chemistry," no matter where it is taught, has a reputation of being difficult. That need not be true for you if you attend class, you put time into studying the material, and that you do the problems. This course will be difficult for those of you that don't attend class, those that don't have time to study, those that don't practice. It is imperative that you keep up with the material in this class. You must work to master the material, you must do problems. It has been said that "Organic Chemistry must be read with a pencil." [quoted in Maitland Jones, Jr., 'Organic Chemistry', Third Edition, W. W. Norton and Company, NY.] That is very good advice. If you didn't learn to study effectively last semester, learn now; and learn quickly.
In an effort to force you to stay current, we will have problems due every day in class. These will be collected, the effort assessed, and will contribute to your grade. We will spend time during lecture periods in small group discussions on problems. Students are expected to read the assigned portions of the text before you come to class. Students are strongly encouraged to establish study groups to work on problems.
The laboratory portion of the course will cover the skills necessary to do organic chemistry, with some examples of syntheses.
The major topics covered in the lecture will be structure and bonding of organic compounds, the determination of structure, and several aspects of the reactivity of compounds containing the carbonyl, related functionalities, and doubly and triply bonded C-C compounds. A great deal of stress in lecture will be placed on the organization of the material, which is the most important single skill needed to do well in any organic chemistry course.
- Meetings and Text
The course meets three times a week (MWF 8:30-9:50) in lecture and discussion (Where is not currently known), once a week in laboratory (several sections available, see laboratory below, and twice a week in an optional, but highly recommended, review session.
I am required to attend all the lectures. So are you. To repeat: You are required to attend all the lecture and laboratory sessions. It is fairly easy to predict if a student is going to fail this class: simply look at her attendance record.
The text is Organic Chemistry, fifth edition by Bruice, Pearson Prentice Hall, 2007, which is available in the bookstore. The text is not absolutely necessary for the course (no problems will be assigned directly from the text), but it is a little hard to imagine doing without it. A set of molecular models is highly recommended; sets are available in the chemistry stockroom, Sabin-Reed, B-21. You will need exact change ($36 is change??) or a check made out to Smith College.
- Modes of Instruction
Classes will not be pure lecture, but will vary between lecture, problem solving, and question and answer sessions. You will be given reading assignments almost daily and should keep up with these assignments. At times during class periods we will break up into small groups and solve problems. Did I say that attendance in class is necessary?
CHREM is an acronym for "chemistry review in the early morning". This is a problem and review session that will start each morning before class (at 8:00) in the lecture room and last until class starts. I know it is early! And we will have another review period on Friday afternoons, but there is nothing like daily (well almost) immersion to help you through organic.
- Problem Sets
In addition to the daily problems, most of which will be quite easy, I will distribute other problem sets with questions more like those you might expect on exams. These will not be collected, but will serve as a starting point for discussions at weekly review sessions. You should put time and effort into the problem sets as doing problems, with a pencil, is the only way to learn organic chemistry.
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Grading:
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The assignment of grades in this course is required by the College. Many of the assessments made are designed to help keep you up with your work in the course. Grading in this course is based on 1000 points, distributed among various assessment methods as follows:
Distribution of Points Among Various Assessment Tools
| Problem Sets |
100 points |
| Quizzes (2) |
100 points |
| Exams (3) |
450 points |
| Final |
200 points |
| Laboratory |
150 points |
Your letter grade in the course will depend on the number of points out of the thousand available that you obtain as follows
Letter Grades Assigned to Points in Course
| A |
>80% of points |
| B |
>65% of points |
| C |
>50% of points |
| D |
>40% of points |
(Plus and minus attachments to these letters will occur near the respective limits of the ranges.)
Please note also that several different faculty members will assign grades for the laboratory portion of the course; if necessary, I reserve the right to "normalize" these laboratory grades so that all sections are treated in a fair and equitable manner. In the past laboratory grades have seldom reduced a student's grade, and sometimes raise it. There is a reverse side to this: one very effective way to lower your grade significantly is to skip a laboratory. The laboratory is integral to the course; if a student misses an excessive number of laboratory sections she is subject to failure in the course.
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Schedule:
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The schedule of examinations is given below. Please note the dates now so that you may plan ahead for those weeks of the semester when you have several different
courses demanding work. Permission to postpone an examination will not be given except in exceptional circumstances.
Important Dates in CHM222 in Spring, 2008
| Classes Begin |
28 Jan |
| Take Home Quiz I |
15 Feb, due 18 Feb |
| Rally Day |
20 Feb |
| Take Home Quiz II |
29 Feb, due 3 Mar |
| Exam One |
10 to 12 Mar |
| Spring Break |
15 Mar |
| Exam Two |
7 and 8 Apr |
| Exam Three |
28 and 29 Apr |
| Finals |
6-9 May |
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Honor Code:
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Section 2 of Chemistry 222 is a Smith College course: the Honor Code applies. Unless otherwise indicated, any work that you submit for a grade must be your own work. Specifically, the take home quizzes, the examinations during the semester, the final examination, and laboratory reports must be solely your own work. During an examination period you may not discuss the examination in any way with other students. While taking an exam, the Honor Code requires that you keep your eyes on your own paper and that you take reasonable precautions to keep others from reading your paper. In this course you may work with others in the class on the problem sets; such a practice is encouraged. In classroom discussions, you will be encouraged (or required) to work with others and material collected in those sessions will clearly be the your work as well as that of others. If in the laboratory you do an experiment with someone else, your written report of that experiment must say with whom you did the experimental work, but the written work submitted for a grade must be your own unless the instructor indicates otherwise. Before you obtain data from someone else and use it in your own written report, you must ask for permission to do so from the instructor, and must state in the report from whom you obtained the data.
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Course Outline:
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- Introduction and preliminaries
- Spectroscopy
- Nucleophilic Addition to Ketones and Aldehydes
- Substitution Reactions of the Acyl Group
- Addition to Alkenes and Alkynes
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Laboratory Schedule:
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Laboratory Schedule
| 30 Jan to 1 Feb |
Solubility Tests |
| 4-8 Feb |
Purification of a solid by recrystallization |
| 11-15 Feb |
Thin Layer Chromotography |
| 18-22 Feb |
Molecular modeling |
| 25-29 Feb |
Identification of unknowns by IR and NMR |
| 3-7 Mar |
IR, NMR Workshop |
| 10-14 Mar |
Reactions of Grignard Reagents, Part I |
| 24-28 Mar |
Reactions of Grignard Reagents, Part II |
| 31 Mar-4 Apr |
Reactions of Grignard Reagents, Part III |
| 7-11 Apr |
Addition to an Alkene, I |
| 14-18 Apr |
Addition to an Alkene, II |
| 21-25 Apr |
Bromonation of Stilbene |
| 28 Apr-2 May |
TBA |
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The grading is finally finished. The Grade Query form is up to date for the entire course grade. Your PIN number is the 5th, 6th, 7th, and 8th digits of your "99" number. If you have trouble, let me know. 1544 19/v/08