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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, Ford Hall 311
Phone, X3836
Email, rlinck(at)email.smith.edu
Reviews: CHREM Sessions, M, W, F, 0800; Also, T, 1600;
Office Hours, Tu, 8-12; 1-3; Th 10-11; F, 10-12; or by appointment.
Tutor's Hours:
Kelly: Su, 2-4; M, 4-6; T, 6-8;
Caitlin: Su, 4-6; W, 4-6, Th, 7-9
| Lecture date | Objective of lecture: In all cases insert the words "Be able to" before the expression. |
|---|---|
| Part I. Preliminaries | |
| Jan 27 |
give electronic configuration of Li through F and Na through Cl. know the number of valence electrons in each of those elements. draw simple Lewis structures. predict polarity of bonds. draw line structures. |
| Jan 30 |
make simple (angular) atomic orbital drawings. understand the constructive and destructive overlap of atomic wave functions. |
| Feb 01 |
distinguish between a σ and π bond. understand hybridization of atomic orbitals. use hybrids to predict the presence of a π bond. build a simple m.o. diagram. |
| Feb 03 |
use nomenclature to communicate. use the three tools: (1) epwa, (2) ihd (called 'hydrogen deficiency index' by Klein and 'element of unsaturation' by Wade) and (3) carbon level. |
| Feb 06 |
understand an epwa approach to the reaction of Br2 with an alkene. draw a zig-zag structure and a Newman projection. 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 08 |
answer the question 'How would you make ...?' use the M+ peak in mass spectroscopy. use M+1 and M+2 mass spectral information. |
| Feb 10 |
understand four points about IR spectroscopy. use IR to discern the functional group. |
| Feb 13 |
explain the basic aspects of 1H nmr. predict the chemical shift of various kinds of protons. use integration of 1H signals effectively. |
| Feb 15 |
explain the anisotopic shielding in benzene and acetylene. solve simple nmr problems from integration and chemical shifts. |
| Feb 17 |
use the n+1 rule of spin coupling to predict the number of neighbors. use the advanced spin rule 1, the n+n'+1 rule. |
| Feb 20 |
express the five advanced spin rules. solve 1H structure problems. |
| Feb 22 |
understand the chemical shifts in 13C spectra. solve spectral problems. |
| Part III. Addition to carbonyls and related reactions | |
| Feb 24 |
express a Ka in terms of concentrations. know the relative Ka and pKa of a pair of acids. |
| Feb 27 |
state the most important factor in relative acidity. 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. |
| Feb 29 |
work with the sulfur analogue of a Wittig. synthesize an epoxide. understand the third factor in relative acidity. use acetylide anions as a C(-) reagent for three classes of compounds. |
| Mar 02 |
see why resonance structures affect relative acidity. order carbocations in terms of relative stability. |
| Mar 05 |
write a mechanism for the formation of alkenes during Grignard synthesis workup. understand the rotation of plane polarized light. 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 07 |
use 'carbon level' to organize material. synthesize an alcohol in three ways. argue that hydration of an alkene is reversible whereas a Grignard reaction is not. synthesize an alkene. |
| Mar 09 |
show that epoxides can be opened regioselectively. prepare a carbonyl compound by oxidation of an alcohol.synthesize compounds based on reactions to date. differentiate between those nucleophiles that add to a carbonyl group reversibly and those that add irreversibly. |
| Mar 12 |
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. show the mechanism of gem-DIN formation (hemiacetal (hemiketal) and acetal (ketal) formation). predict cases where the equilibrium lies toward products. |
| Mar 14 |
use acetals and ketals as protecting groups. use epwa to write the mechanism of nitrogen derivative addition to the carbonyl group. carry out reductive animation of a carbonyl group. |
| Part IV. Addition to Carboxylic Acid Derivatives and related reactions | |
| Mar 16 |
understand the rearrangement of oximes to amides. synthesize nitriles from aldehydic oximes. use the Wolff-Kishner conditions to prepare alkanes. use carboxylic acid derivative (CAD) nomenclature. |
| Mar 26 |
account for subtle features of carbonyl stretch energy. understand the nmr of amides. use acid/base chemistry to predict CAD substitution chemistry. determine when excess reagent is required in CAD substitution. synthesize acyl chlorides from acids. |
| Mar 28 |
appreciate subtle aspects of CAD substitution. synthesize amides from acids. understand why nitriles should be discussed as CAD.embrace the cl3 to cl2 or cl1 concept. intelligently choose BH4- or AlH4- as a reagent. |
| Mar 30 |
appreciate the role of aluminum oxophilicity in AlH4- reactions. use H- reagents to achieve desired goals. 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. |
| Apr 02 |
use organo copper reagents. use epwa to show reduction of nitriles. |
| Apr 04 |
show how α,β-unsaturated ketones can be attacked remotely. 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. |
| Apr 06 | use appropriate C- and H- reagents for effective synthesis. |
| Part V. Stereochemistry | |
| Apr 09 |
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 11 |
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. |
| Apr 13 | use the R/S nomenclature system. |
| Apr 16 |
deal with compounds with multiple chiral centers. draw the structure of an enantiomer, given its name. outline how to separate enantiomers. classify compounds as constitutional isomers, conformers, diastereomers, or enantiomers. |
| Part VI. Alkene and Alkyne Nucleophiles | |
| Apr 18 |
name alkenes. use epwa to show how an alkene attacks Br2. understand the stereochemistry of the addition of bromine to an alkene. |
| Apr 20 |
extrapolate your knowledge to show formation of bromohydrins and bromoethers. understand the stereochemistry of hydration of alkenes. appreciate the range of rearrangements in hydration and hydrobromonation reactions. |
| Apr 23 |
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. |
| Apr 25 |
describe the synthsis of a peracid. make an epoxide from an alkene. understand the stereochemistry of opening of an epoxide. use OsO4 to create diols. |
| Apr 27 |
show the mechanism of the formation of a molozonide and a ozonide. understand the oxidative and reductive products of an ozonide. use HBr with peroxide to get addition to alkenes. produce alkanes from alkenes. prepare alkynes. add HBr or H2O to alkynes. |
| Lecture date | Readings (before lecture) in Klein | Readings (before lecture) in Wade | Daily Problems due before lecture on the date indicated |
|---|---|---|---|
| Jan 27 | 1-12,49-56 | 1-18 | |
| Jan 30 | 13-18 | 40-46 | 1, 2.0, 3.5, 4, 5, 8 |
| Feb 01 | 18-30 | 46-57 | 12, 13, 16, 18.0.1. |
| Feb 03 | 137-147,566-570,917-920 | 85-90, 423-426, 808-811 | 14, 17.0, 17.1, 17.2, 18.0, 19 |
| Feb 06 | 155-163 | 96-102 | 21, 23, 23.0., 24.0, 24.0.1.1-24.0.1.3., 25, 30.0. |
| Feb 08 | 695-705, 672-694 | 539-545, 510-539 | 27, 31, 36, 42, 44.0, 51, 55 |
| Feb 10 | None (or finish last assignment) | None (or finish last assignment) | 57, 57.0, 58.0, |
| Feb 13 | 718-734 | 561-569 | 58, 59.0, 59 |
| Feb 15 | 734-739 | 569-577 | 60.0, 64.0, 69, 69.0, 70, 72, 74 |
| Feb 17 | 739-754 | 578-590 | 77.0, 79.0, 80, 81, 88 |
| Feb 20 | None | None | 88.0, 89, 89.0, 91.0 |
| Feb 22 | 754-759 | 601-611 | 92, 93, 94.0.3-94.0.6 |
| Item | Link |
|---|---|
| Daily Exercises, Set One, Version 1.1. | 1-56 |
| Hints and answers to some daily exercises | 1-115, 27/xii/11 version |
| Daily Exercises, Set Two, Version 1.2. | 57-115 |
| Practice | Quiz |
| Answers to Practice | Quiz |
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 aims are several: We will explore this chemistry on the basis of a few unifying principles so that we can find order in what seems to be 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 sweet; it is both rich and varied. At the same time, 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. It is not my goal in this course to force you to memorize a bunch of stuff, but rather to be able to use certain relationships to understand, to make logical predictions about the solution to a problem. That is not to say that there are not things to know, but if I can know them--as filmsy as my memory is--so can you. Nevertheless, as much as anything else, organic chemistry is a vehicle to show you how to think logically about the unknown.
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 do all three of these things: If you attend class, without exception. If you put time into studying the material--that means doing more than just doing problem, more than just reading your notes-- and, although you need to do more, you do need to do the problems. This course will be difficult for those of you that don't attend class; to those of you that don't have time to study, or who study ineffectively; and to those of you that don't do practice problems.
Adjacent is a plot of points on daily problems versus score on the final from an earlier 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 to do well. It has been said that "Organic Chemistry must be read with a pencil." [quoted from 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 exhort 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. This does not mean coming to CHREM--see below--and copying my answers down on the paper and then handing it in. It requires you working on the problem. Daily problems sets will be graded on a scale of checks: you can expect a check for nominal effort, but it will require a real show of effort to get a check plus, or hopefully, a check double plus. On the other hand, a lackadaisical effort will earn you a check minus; not turning in the work will net a zero. We will also spend time during lecture periods individually or in small groups discussing problems. I am planning on using rf response device technology--see below--to allow you to participate in classroom discussions. You can probably do this course without the text book if you take effective notes (don't just copy what I write) and study them, but you are responsible for the material in the indicated portions of the text. You should try to spend time on organic chemistry at least six days a week. That time should be
Students are strongly encouraged to establish study groups to work on problems. Study groups are also a very good way to review material: ask each other questions, critique answers until they are correct, ask "what if" questions of each other.
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, in Stoddard G2, and once a week in laboratory (several sections available, see laboratory below, and four times a week in optional, but highly recommended, review sessions.
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 officially is Klein, Organic Chemistry, Wiley, 2012. It will be available in the book store (or as an ebook on the Wiley website). However, I will post reading as well in the book we used last year: Wade, Organic Chemistry, Seventh Edition, Prentice Hall, 2010. You can use any text you want if you simply find in the index the topic we are covering and read about that subject. Clearly the Klein text is not absolutely necessary for the course (no problems will be assigned directly from the text), but unless you are a practiced and efficient note taker, it is a little hard to imagine doing the course without some book, although others have done so. A set of molecular models is often useful for students who have some difficulty picturing three dimensional structures (which are important for organic chemistry). Model sets are available in the chemistry stockroom, Ford Hall 026. You will need exact change ($48 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! We will have another review session on Tuesday afternoon, but there is nothing like daily (well almost) immersion to help you through organic. In 2009 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 reviewing your notes (with a pencil in hand), doing problems, and coming to review sessions.
We will use radio frequency (rf technology) devices, "clickers", in this class. I will often ask a question and offer you a set of answers. I expect you to give me the answer through the clicker. These are useful for me to see how the class is responding and to identify those students that are not getting the material, as well as those that are not participating in class. You should check out a clicker within the first week of classes and be sure that I have the clicker number.
Problem SetsYou will be provided with a large number of problems to do. Some of these will be assigned as daily problems and will be collected and effort assessed. The rest are problems you should do; they will also serve as a starting point for the 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 and Participation | 150 points |
| Quiz | 50 points |
| Exams | 450 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 | >75% of points |
| B | >60% of points |
| C | >45% 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 material in this course, by its very nature, is comulative. This has advantages for you: The second and third exams, and the final, will contain problems that come from earlier in the course. If you did poorly on a certain problem earlier, and do well on the later exam, your grade on the earlier exam will be raised to reflect your achievement.
The schedule of quiz and examinations is given below. Permission to postpone an examination or quiz will not be given except in exceptional circumstances. Students should let me know in advance of the need to postpone an examination.
| First Day of THIS Class | 27 Jan |
| Quiz Due | 13 Feb |
| Rally Day | 23 Feb |
| Drop a Course | 29 Feb |
| Exam One | 2-4 Mar |
| Spring Break | 17-25 Mar |
| Exam Two | 30 Mar-1 Apr |
| Exam Three | 27-30 Apr |
| Last Day of Class | 2 May |
| Finals | 8-11 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 quiz, 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.
