Preliminary! CHEMISTRY 350 SPRING 2011 (Sec 1; CRN 25088)
Professor: John Bartmess
Office: BU 601 | Phone: 974-6578 | Email: bartmess@utk.edu
Class time and location: BU 555, TR 2:10-3:25 PM
NOTE: I have a very aggressive junk mail filter. If you email me, please include "Chem 350" in the
subject, so my junk mail filter doesn't kill it.
Blackboard: I will use both the email function and links to documents in the Blackboard system this
semester. It is your responsibility to either routinely read your "formal" @utk.edu/@tennessee.edu email
account, or to have it forwarded to an account that you do check. Because providers like Yahoo/ Hotmail/
Gmail do not generate bounce messages when mailboxes are full, I have no idea if you are getting things
or not if your email is set up that way. You are responsible for email sent to your @utk address.
Office Hours: 1:30-2:30 PM Mon; 11:00AM-12:00 R. I'm also glad to make appointments at the end of
the lecture period, or by email, for discussions at whatever time. However, the 30 minutes before the
lecture are NEVER available times, due to my reviewing for the lecture. I reserve Wed. for research.
Hour Exams: 22 Feb (Tues){class 12}, 12 Apr (Tues){class 26}
Note that these are evening exams (7:00-8:30 PM) due to room size. These times are mandatory;
no exceptions will be made. Those times were stated in the timetable when you registered for the class,
and you have thus agreed to them. Your worst one of these two (relative to the class average on that
exam) counts 25%, and the other counts 35% , of the course points. Answer keys will be posted in the
glass-front cabinets outside the rear door to BU 415. I will have a Question & Answer session at the
nominal class time that day before each exam.
Final Exam: Mon May 9, 12:30-2:30 PM. 40% of total points. Cumulative in content.
Text: “Organic Chemistry,” 8th. Ed., Carey. Required.
“Student Solutions Manual,” Atkins and Carey (recommended)
This is not just the answers to problems, but a wealth of material that will help you learn. Read!
“Proteus Organic Model Kit" (recommended, though splitting one set with another student is okay) available from Student Affiliates of the American Chemical Society, outside BU 415, 1st full week of
classes. "Framework Molecular Models" are also acceptable.
Chapters 1-11 will be covered this semester, with a few sections omitted (see below). The selected
problems will not be collected or graded, but will be considered fair game for exams (though not
exclusively so).
Background: I expect you to have a reasonable knowledge of certain topics (see below) from General
Chemistry, including equilibrium, acidity (pKa and pH), reaction coordinates, etc. I will announce when I
am assuming some such knowledge and will refer you to certain sections of the General Chemistry text, so
that you can review it if you need to. See below for a further list.
Rules for missed exams: If you miss an exam, you must have a valid, verifiable excuse, presented to me
within 24 hours. For an hour exam, if the excuse is accepted, your grade for that exam will be assigned
based on your performance on the other hour exam, relative to the class average. If the excuse is not
accepted, you will be assigned a zero on that exam. You cannot miss both hour exams and get credit for
the course. If you are failing the course coming into the final, and you miss the final (even with a valid
excuse), a grade of "F" will be assigned.
Exam Regrading: Arithmetic mistakes of addition or transferring points to the front page will be
corrected anytime. For regrading of an answer's content, the exam must be submitted no later than three
class meetings after the exam date, with the number of the question(s) to be regraded clearly marked on
the front. Also, you need the feedback from how you did on a previous exam, to help you study for the
next exam. If you don't pick up your previous exam by three class meetings after the exam, I will deduct
five points from that exam grade.
Class Attendance. This is not a course that you can pass solely by reading the book. I expect attendance
at all classes, though I do assume that you are responsible adults, and thus I will not take attendance. I will
sometimes make announcements in class regarding material to be covered, or exam content, or so forth,
that you will be responsible for knowing. An excuse of “I didn’t know” is not acceptable. Pop quizzes to
verify attendance are also possible.
Snow policy: If UTK is officially closed due to weather at the hour of an exam, the exam will be given at
the next class meeting. If UTK is open, but weather keeps you from attending, contact me within 24 hours
to explain your problem.
University Rules (Undergraduate Catalog, p. 44)
- A passing grade in both Chem 120 and Chem 130 is a pre-requisite for taking Chem 350. If you have not
done this, there's no point in taking 350; I'll have you adminstratively dropped from the class.
- You are not allowed to take a course more than three times. If you have taken Chem 350 three times
already and received an assigned grade (including WP/WF), you cannot take it again for credit at UTK.
- You cannot repeat a course for credit in which you have received a grade of "C" or better.
- I will use minus grades, as well as plus ones.
Disability Services Statement: Students who have a disability that require accommodation(s) should
make an appointment with the Office of Disability Services (974-6087) to schedule an appointment to
discuss their specific needs.
WP/WF Rules: At the time you apply for a WP/WF withdrawal, if the sum of your exam points is less
than 2/3 of the summed class average on the exams given up to that time, the grade will be WF. This
cutoff is not negotiable.
Future letters of reference: I do not do "cold" letters of reference, based on a single future meeting with
someone. If I don't get to know you somewhat, through your visiting me in my office with questions this
semester, I will decline to write a medical/dental/pharmacy reference letter in the future.
Problems in the Text: There are two kinds of problems in the text.
- "Study Problems" have the answers right after the problem. It is to your considerable advantage to cover
that answer and work the problem in writing first.
- There are "regular" problems throughout each Chapter and continuing at the end. The answers to these
are in the Solutions manual. The assigned problems listed below come from these "regular" problems.
Assigned Chapters and Sections, and Practice Problems, “Organic Chemistry," 8th Ed., Carey.
Note: All dates are approximate. You must keep up in class to know where we are, and what will be
covered on exams. I could either be ahead of or behind this schedule.
Jan 13,18
Chapter 1 "structure": all
Problems: 1-24, 27-35, 37-59, 63-65, 67-71
Jan 20,25
Chapter 2 “Hydrocarbons” omit 2.16
Problems: 1-5, 7-11, 17-23, 26, 27, 31, 37, 39, 42, 49
Jan 27, Feb 1,3
Chapter 3 "Conformation": omit 3-14-3.15
Problems: 1-3, 5-7, 9-10, 14-26, 29-31, 34, 36, 39
Feb 8,10,15
Chapter 4 "alcohols & haloalkanes” Feb 22(Tues) Exam 1 7:00 PM
Problems: 1-5, 7-15, 17-18, 20-22(not 22g), 25-29, 31-32, 34, 36-44, 46-48, 50, 52, 54-61
Feb 17,22
Chapter 5 "elimination": all
Problems: 1-29, 33-38, 40-49
Feb 24, Mar 1,3
Chapter 6 "alkenes: additions”: omit 6.22
Problems: 1,3-13, 15-20, 22-24, 26-28, 30-39, 41-43, 47-50, 52-64
Mar 8,10,22,24
Chapter 7 "stereochemistry":
Problems: 1-3, 6-12, 14, 17-41, 43-47a, 48-50
Mar 29,31,Apr 5,7
Chapter 8 "substitution":
Problems: 1-36,38-44,46-47
Apr 12,14
Problems: 2-35
Chapter 9 "alkynes": omit 9.1
Apr 12(Tues) Exam 2 7:00 PM
Apr 19,21
Chapter 10 "conjugation":
Problems: 1-2, 4-10, 12-18, 21-24, 26-31, 33-35, 39-41, 43
Apr 26,28
Chapter 11 “aromatics": omit 11.8-11.10, 11.16-11.18
Problems: 1-3,6-11,14-16,20-21,23-25,27-29,31-34, 35(not e), 36(not f),37-38,40-46,48-53
Final Exam: Mon May 9, 12:30-2:30 PM.
Prerequisites for Chemistry 350:
Successful completion of General Chemistry 120+130 or their equivalents. In our 120+130 sequence we
cover the topics and terms listed below. It is expected that you will come to Chem 350 with a working
knowledge of these topics and terms. If you are not familiar with any of these, you should review them in
a general chemistry text. Chapter references below are to Brown, Lemay, Bursten, Murphy, 11th Ed.
A Atomic Structure{Ch. 6}
(1) Protons (2) Electrons (3) Neutrons (4) Isotopes
B Divisions of the Periodic Table{Ch. 7}
(1) Metals, nonmetals, and metalloids; (2) Main group elements (13-18), transition series elements(3-12),
and inner transition series elements (the lanthanides and actinides)
(3) Trends in atomic properties (ionization energies, size, electronegativity, etc.)
C Electron Configurations of Atoms and Ions{Ch. 6}
D Electron-dot (Lewis) Structures{Ch. 8}
(1) For atoms and ions, monatomic and polyatomic; (2) For covalent molecules that follow the octet rule
(3) For covalent molecules that do not follow the octet rule
E Geometries of Molecules and Ions Based on VSEPR Theory{Ch. 9}
F Formal Charge{Ch. 8}
G Theories of the Covalent Bond{Ch. 8, 9}
(1) Hybridization; (2) Resonance and resonance structures; (3) Sigma and Pi Bonds
H Thermochemistry and Thermodynamics{Ch. 5, 8.8, 15}
(1) Enthalpy changes for reactions, ΔrxnH; (2) Enthalpies of formation, ΔfH
(3) Bond energies; (4) Difference between enthalpy ΔH, and free energy, ΔG
I Chemical Kinetics{Ch. 14}
(1) Reaction rates (2) Reaction orders (3) Catalysts (4) Activation energies (5) Transitions states (6)
Reaction profile or coördinate
J Chemical Equilibria and Equilibrium Constants{Ch. 15}
K Hydrogen Bonding{Ch. 11.2}
L Acids and Bases{Ch. 16}
(1) Brønsted-Lowery concept; (2) Lewis concept; (3) Relative strengths of acids and bases
(4) Conjugate acid-base pairs; (5) Acid and base ionization constants, Ka and Kb
(6) pH, pKa
The Skills Needed for Success in Organic Chemistry
This is not a course where you can get an A by simply regurgitating what you are told in lecture. Your
grade depends on solving problems, while using the information that you have learned in class. There are
certain skills that are very important in this:
Learning to visualize structures in 3D: The "Mind's Eye”
Recognition and comprehension of a 3D structure from a 2D representation
Use of model kits as a training tool.
Are two 2D structures the same (“superimposable”) or different, when drawn in a different orientation?
Do they have same connectivity?
Are they mirror images, or identical, or both?
Recognition of functional groups and special structural features: learning what’s important in a molecule
to a given problem, and what’s just there to hold the rest together.
Memorization of information: Visual vs. auditory learning
Mental organization of that memorized information, so as to find what's needed quickly.
Data sorting and selection for a given problem:
Judging whether a piece of information is needed or irrelevant to the problem at hand
Putting the information together in a form that allows answering the problem.
Checking: Is this the problem to that answer?
Flow charts for certain types of problems:
nomenclature
solution of nmr spectra
synthesis
recognition of substructures
Problem Solving Skills:
Read the problem twice; be sure you understand what is being asked.
Be sure you know what the structure of the molecule is.
Don't forget what the problem is halfway through your answer.
Plan an answer before you start writing.
Take a complex problem apart into simple pieces, and do them stepwise until it’s done.
You need to realize that Chem 360 is not a separate course, but a continuation of Chem 350. You must
know and be able to use the Chem 350 material, in order to succeed in Chem 360.
Exam skills: Because your grade in this course rests heavily on being able to solve complex nonmathematical problems, you need to be thinking clearly while taking the exam. You must plan your
studying so that you get at least 6 hours of sleep on the night before the exam, or you won’t be clearheaded enough to do well. This means you have to study (both memorize material and practice solving
problems) as you go, not put it off until the last minute. Generations of students have proven that this is a
course that CANNOT be “crammed” the night before the exams.
The “But I studied so hard…” syndrome.
Students who do poorly on an organic chemistry exam will often offer the above statement in frustration.
Although studying hard – memorizing the information – is necessary for this course, it is not the only
thing needed on a student’s part to succeed. Success here depends on your ability to use that information
in solving logical but non-numeric problems. There is a pattern to the processes needed to solve such
problems, and it is often a lack of following that pattern which is the reason for failure.
You cannot memorize every possible specific organic structure, plus how it reacts with all possible
reagents. Instead, students memorize generic structures, as arrangements of atoms called “functional
groups”. These tend to react the same way with a given set of reagents, regardless of the rest of the
structure that is more distant from the functional group. Nevertheless, in a test problem you will be
given a specific chemical structure, not a generic one. You must thus:
1. decide what generic functional groups are present in that specific reactant. (= simplify the problem!)
2. from your memory, retrieve the information on how that generic group reacts with the reagents given.
(= get the simple answer!)
3. apply that pattern of reactivity to the specific reactant, and work out what the product structure will be.
(= work out the more complex, real answer!)
4. now consider if there are any additional, secondary aspects to the structure of the reactant, that might
modify the outcome. For example, there are cases in some substitution reactions, when one functional
group normally simply replaces another exactly in its place, but if certain very specific structures are also
present, the whole carbon skeleton rearranges to a new structure. Likewise, which site of two possible
places a reaction can actually occur, or which of two sides of a molecule a reagent can attack, must be
considered. These secondary aspects will be introduced gradually over the course of Chem 350, often
requiring you to go back to “re-memorize” a prior generic reaction, with new information about it.
There are other kinds of problems (you are given the organic reactants and products, and need to
determine the reagents needed, or are given reagents and products, must figure out the reactants) that
require a slightly different pattern than stated above. It is still the same core steps however: figure out the
generic problem from the specific one, figure out what information you have that applies, then apply it to
the specific problem and work out the specific answer.
Practice Solving Problems
In order to learn to solve problems correctly, you must practice actually solving them. That’s why there
are so many problems in your text. However, to practice your skills with the given problems, you must use
them effectively. The first time you work a problem, it’s a good test of the skills you need on an exam.
The second and later times you re-work it, it is instead a test of your recall memory of your first try, and
thus is not effective in your mastering problem solving skills. Thus:
1. Do not attempt the problems before you memorize the facts. Some students will try to work the problem
without studying the material, assuming that if they are successful, then they don’t have to do the hard
work of memorizing. This will not help them on the exams, for two reasons: even if they get it right, they
have not learned the breadth of the material, so might not do well if a slightly different problem is asked
on the exam. Also, if they get it wrong, they’ve wasted that problem as a test of how they do in solving
problems. As noted above, the second time through solving a problem is not an effective test for how
you’ll do on an exam.
2. Don’t just work out the answer to a problem in your head; take the time to write down your answer
including some notes as to how you arrived at that answer. That way, when you find you’ve done it
wrong, you can’t just say “Oh I really knew that.” The evidence that you didn’t is there on paper. It’s more
work to write an answer down, but also much more effective in learning. The process of writing it down
helps you remember.
3. If you get the wrong answer to a problem, there are two things you need to do: not only learn the correct
answer, but also figure out where you went wrong in the process of getting your answer. The latter is the
principal way people learn how to solve problems of this type correctly.