Home > Academics > Academic Programs > Chemistry Home > Chemistry Academics > Current Courses > Chm 222, Section 1
The information on this page is for students in Section 1 of CHM 222, Chemistry II: Organic Chemistry. This is the second course in a four semester sequence of introductory chemistry. In this course we will explore structure in organic compounds using simple bonding models and verify those structures through the use of tools such as nuclear magnetic resonance and infra-red spectroscopies. We will also use the structure and concepts of acidity to study the reactions and synthesis of compounds of carbon. Our focus will be mainly on addition to double bonded compounds, both C=O and C=C. For more detail, click on the syllabus link in the menu on the right.
Robert Linck
Office, Sabin-Reed 429
Phone, X3836
Email, rlinck(at)email.smith.edu
Reviews: CHREM Sessions, M, W, F, 0800; T, 1600; F, 1400.
Office Hours, Tu, 8-11; Th 10-12; 1-3; F, 1-2; or by appointment.
| Lecture date | Objective of lecture: In all cases insert the words "Be able to" before the expression. |
|---|---|
| Part I. Preliminaries | |
| Jan 26 |
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. predict polarity of bonds. draw line structures. |
| Jan 28 |
make simple (angular) atomic orbital drawings. understand the constructive and destructive overlap of atomic wave functions. distinguish between a σ and π bond. understand hybridization of atomic orbitals. |
| Jan 30 |
use hybrids to predict the presence of a π bond. use nomenclature to communicate. |
| Feb 2 |
use concept of ihd. understand an epwa approach to the reaction of Br2 with an alkene. draw a zig-zag structure and a Newman projection. |
| Feb 4 |
appreciate why BH4- reacts with a carbonyl compound. use a Grignard or an alkyl lithium reagent to make a new C-C bond. |
| Part II. Spectroscopy | |
| Feb 6 |
answer the question 'How would you make ...?' use the M+ peak in mass spectroscopy. understand four points about IR spectroscopy. |
| Feb 9 |
use IR to discern the functional group. explain the basic aspects of 1H nmr. predict the chemical shift of various kinds of protons. |
| Feb 11 |
use integration of 1H signals effectively. explain the anisotopic shielding in benzene and acetylene. |
| Feb 13 | use the n+1 rule of spin coupling to predict the number of neighbors. |
| Feb 16 | use the advanced spin rule 1, the n+n'+1 rule. |
| Feb 20 |
express the five advanced spin rules. solve 1H structure problems. understand the chemical shifts in 13C spectra. |
| Feb 23 | solve structural problems with spectral data. |
| Part III. Addition to carbonyls and related reactions | |
| Feb 25 |
express a Ka in terms of concentrations. know the relative Ka and pKa of a pair of acids. state the most important factor in relative acidity. |
| Feb 27 |
understand the effect of acidity on a Grignard reaction. state the second factor important in relative acidity. distinguish between Grignard and alkyl lithium reagents. show how a Wittig reagent is formed and reacts. work with the sulfur analogue of a Wittig. synthesize an epoxide. |
| Mar 2 | Classes are canceled |
| Mar 4 |
understand the third factor in relative acidity. use acetylide anions as a C(-) reagent for three classes of compounds. see why resonance structures affect relative acidity. order carbocations in terms of relative stability. |
| Mar 6 |
write a mechanism for the formation of alkenes during Grignard synthesis workup. write mechanisms for a Grignard reaction in which alkene formation is enhanced or avoided. use thermodynamic data to determine relative stability of alkenes. list alkenes in terms of relative stability. |
| Mar 9 |
determine the 'carbon level'. synthesize an alcohol in three ways. argue that hydration of an alkene is reversible whereas a Grignard reaction is not. |
| Mar 11 |
show that epoxides can be opened regioselectively. synthesize an alkene. prepare a carbonyl compound by oxidation of an alcohol. synthesize compounds based on reactions to date. |
| Mar 13 |
differentiate between those nucleophiles that add to a carbonyl group reversibly and those that add irreversibly. use epwa to write the mechanism of addition of CN-, OH-, and water in the presence of H+. write the mechanism for oxidation of an aldehyde. |
| Mar 23 |
show the mechanism of hemiacetal (hemiketal) and acetal (ketal) formation. predict cases where the equilibrium lies toward products. use acetals and ketals as protecting groups. |
| Mar 25 |
use epwa to write the mechanism of nitrogen derivative addition to the carbonyl group. carry out reductive animation of a carbonyl group. understand the rearrangement of oximes to amides. synthesize nitriles from aldehydic oximes. use the Wolff-Kishner conditions to prepare alkanes. |
| Part IV. Addition to Carboxylic Acid Derivatives and related reactions | |
| Mar 27 |
use carboxylic acid derivative (CAD) nomenclature. account for subtle features of carbonyl stretch energy. understand the nmr of amides. use acid/base chemistry to predict CAD substitution chemistry. |
| Mar 30 |
determine when excess reagent is required in CAD substitution. synthesize acyl chlorides from acids. appreciate subtle aspects of CAD substitution. synthesize amides from acids. understand why nitriles should be discussed as CAD. |
| Apr 1 |
embrace the cl3 to cl2 or cl1 concept. intelligently choose BH4- or AlH4- as a reagent. appreciate the role of aluminum oxophilicity in AlH4- reactions. use H- reagents to achieve desired goals. |
| Apr 3 |
write the general mechanism of a C- reagent attacking a CAD. deal with special cases: Grignards on acids and amides. write the mechanism of reduction of acids/amides with alkyl lithium reagents. use organo copper reagents. use epwa to show reduction of nitriles. show how α,β-unsaturated ketones can be attacked remotely. |
| Apr 6 |
understand potential energy curves showing kinetic/thermodynamic control. predict which carbonyl compounds will give kinetic products. use a table of soft reagents to predict thermodynamic control. use appropriate C- reagents for either pathway. |
| Part V. Stereochemistry | |
| Apr 8 |
discuss reasons for instability of alkane rings. use thermochemical measurements to assess stability. draw a cyclohexane ring showing axial and equatorial hydrogen atoms. show that a cyclohexane ring flip interchanges axial and equatorial positions. |
| Apr 10 |
understand cis and trans isomers in ring compounds. see how handedness occurs in tetrahedral carbon compounds. use the terms enantiomers and chiral. predict the occurrence of enantiomers using symmetry. deal with compounds with multiple chiral centers. |
| Apr 13 |
Classify compounds as constitutional isomers, conformers, diastereomers, or enantiomers. draw the structure of an enantiomer, given its name. outline how to separate enantiomers. |
| Part VI. Alkene and Alkyne Nucleophiles | |
| Apr 15 |
name alkenes. |
| Apr 17 |
use epwa to show how an alkene attacks Br2. understand the stereochemistry of the addition of bromine to an alkene.extrapolate your knowledge to show formation of bromohydrins and bromoethers. understand the stereochemistry of hydration of alkenes. |
| Apr 20 | appreciate the range of rearrangements in hydration and hydrobromonation reactions. |
| Apr 22 |
show the oxymercuration/demercuration mechanism for alcohol formation. use BH3.THF to accomplish hydrations with the reverse regioselectivity. use BH3.THF to form amines. recognize the usefulness of BBN. describe the synthsis of a peracid. make an epoxide from an alkene. |
| Apr 24 |
understand the stereochemistry of opening of an epoxide. show the mechanism of the formation of a molozonide and a ozonide. understand the oxidative and reductive products of an ozonide. |
| Apr 27 |
use OsO4 to create diols. use HBr with peroxide to get addition to alkenes. produce alkanes from alkenes. prepare alkynes. add HBr or H2O to alkynes.add water to alkynes to make ketones. form aldehydes from alkynes. synthesize cis alkenes from alkynes. |
| Apr 29 | Review |
| May 1 | Review |
| Lecture date | Readings (before lecture) | Daily Problems due before lecture | Other Problems |
|---|---|---|---|
| Jan 26 | 1-11; 35-43 | ||
| Jan 28 | 49-59 | 1-6 | 1-4 |
| Jan 30 | 12-23 | 7-10 | 5-6 |
| Feb 2 | 77-82; 448-449 | 11-15 | 7-11 |
| Feb 4 | 611-614 | 16-19 | 12-20 |
| Feb 6 | 445-469 | 20-28 | 21-27 |
| Feb 9 | 397-406 | 29-30 | None |
| Feb 11 | 406-408 | 31-36 | 28-31 |
| Feb 13 | 408-425 | 37-43 | 32-36 |
| Feb 16 | None | 44-45 | None |
| Feb 20 | 426-434 | 46-48 | 37-38 |
| Feb 23 | None | 49-51 | 39-45 |
| Feb 25 | 137-153 | None | 46-49 |
| Feb 27 | 497-498, 684-691 | 52-54 | 50-53 |
| Mar 2 | None | None | None |
| Mar 4 | 186-191 | 55-60 | 54-59 |
| Mar 6 | None | 61-62 | None |
| Mar 9 | None | 63-65 | 60-63 |
| Mar 11 | 331-333, 622-623 | 66-69 | 64-70 |
| Mar 13 | 348-350, 608-610 | 70-77 | 71-74 |
| Mar 23 | 635-643 | 78-80 | 75-76 |
| Mar 25 | 669-683 | 81&85 | 77-90 |
| Mar 27 | 701-705 | 82-87&90 | 91-106 |
| Mar 30 | 706-725 | 91-95 | 107-114 |
| Apr 1 | 728-730 | 96-101 | 115-125 |
| Apr 3 | 725-728 | 102-106 | 126-131 |
| Apr 6 | 314-315, 838-844 | 107-111 | 132-140 |
| Apr 8 | 82-96 | 112-121 | 141-168 |
| Apr 10 | 87-96, 110-115 | 122-123.3 | 169-182 |
| Apr 13 | 116-127 | 123.4-127 | 183-186 |
| Apr 15 | 107-110, 270-273 | 128-1/2 of 129 | 187-189 |
| Apr 17 | 248-269 | 129-139 | 190-195 |
| Apr 20 | 194-195, 274-276 | 140-145 | 196-204 |
| Apr 22 | 338-341, 344-345 | 146-152 | 205-212 |
| Apr 24 | 331-337, 341-342, 378-379 | 146,147,151-155 | 213-221 |
| Apr 27 | 276-277 | None | None |
| Apr 29 | None | 157-162 | 222-243 |
| Item | Link |
|---|---|
| Daily Problems, Other Problems | Set One |
| Daily Problems, Other Problems | Set Two |
| Answers to Problem Set One Daily Problems: | 1-28 |
| Answers to Problem Set One Other Problems: | 1-27 |
| Answers to Quiz | One |
| Daily Problems, Other Problems | Set Three |
| Answers to Problem Set Two Daily Problems: | 29-51 |
| Answers to Problem Set Two Other Problems: | 28-49 |
| Answers to Quiz | Two |
| Answers to Problem Set Three Daily Problems: | 52-90 |
| Answers to Problem Set Three Other Problems: | 50-106 |
| Daily Problems, Other Problems | Set Four |
| Special Challenge Problems (These are VERY hard--often pursue side reactions--and are meant to be done only if you find little challenge in the daily and other problems): | 1-7 |
| Answers to Exam | One |
| Typical Problems for Exam | Two |
| Daily Problems, Other Problems | Special Set Four |
| Daily Problems, Other Problems | Set Five |
| Daily Problems, Other Problems | Set Five |
| Daily Problems, Other Problems | Set Six |
| Answers to Practice Exam | Two |
| Answers to Exam | Two |
| Answers to Problem Set Four Daily Problems: | 91-117 |
| Answers to Problem Set Four Other Problems: | 107-162 |
| Answers to Problem Set Four B Daily Problems: | 118-121 |
| Answers to Problem Set Four B Other Problems: | 163-168 |
| Answers to Problem Set Five Daily Problems: | 122-133 |
| Answers to Problem Set Five Other Problems: | 169-183 |
| Isomer Identification | Chart |
| Typical Problems for Exam | Three |
| Answers to Practice Exam | Three |
| Typical Problems for the | Final |
| Answers to Problem Set Six Daily Problems: | 134-167 |
| Answers to Problem Set Six Other Problems: | 190-243 |
| Answers to Problem Set Seven Problems: | 168-250 |
| Answers to Exam | Three |
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" group 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, will 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 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 problems.
Above is a plot of points on daily problems versus score on the final from last year's class. Although the plot shows lots of scatter, note that no one got more than 120/200 on the final without doing at least 60% of the daily problems. In organic chemistry, it is imperative that you keep up with the material. You must work problems to master the material; you must do problems do well. 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 prod you to stay current, we will have problems due every day in class. These will be collected as you enter the room, the effort will be assessed, and that effort will contribute to your grade. To assess that effort requires a lot of work on my part. That I am willing to do this work indicates how important I believe doing daily problems is. We will also spend time during lecture periods individually or in small groups discussing problems. I am planning on using rf response device technology to monitor your participation in classroom discussions. Students are expected either to read the indicated portions of the text or to study your lecture notes carefully every day. You should try to spend time on organic chemistry six days a week. That time should be
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 TextThe course meets three times a week (MWF 8:30-9:50) in lecture and discussion, probably in Stoddard (although that is not currently known for sure) 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, Second edition by Sorrell, University Science Books, 2006, 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 the course 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 InstructionClasses 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 or generate a effective way to study your lecture notes. 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 other review periods on Tuesday and Friday afternoons, but there is nothing like daily (well almost) immersion to help you through organic. Last year about 40% of the students regularly attended CHREM or the afternoon reviews; those students got nearly 70% of the A and A- grades in the course. The 40% of the students that attended reviews got more than 55% of the B and higher grades. Since there is no curve in this class, all of you can do well: Put the odds on your side by doing problems and coming to review sessions.
Problem SetsIn 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.
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:
| Daily Problems | 170 points |
| Quizzes (2) | 80 points |
| Exams | 400 points |
| Final Exam | 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:
| 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.
The schedule of examinations and quizzes is given below. Permission to postpone an examination or quiz will not be given except in exceptional circumstances.
| First Day of Class | 26 Jan |
| Quiz One Due | 9 Feb |
| Rally Day | 18 Feb |
| Quiz Two Due | 23 Feb |
| Exam One | 4-6 Mar |
| Spring Break | 14-22 Mar |
| Exam Two | 1-3 Apr |
| Exam Three | 27-29 Apr |
| Last Day of Classes | 1 May |
| Finals | 5-8 May |
Chemistry 222 is a Smith College course: the Honor Code applies. Any work that you submit for a grade must be your own work unless specifically indicated otherwise by the instructor. The individual quizzes, the three examinations, and the final examinations are work that you are expected to do on your own. Preparation of the daily problems may be the work of a group. You are STRONGLY encouraged to do problems with others.
