YOU MUST PURCHASE
WILEYPLUS FOR THIS
COURSE
see SDSMT Bookstore
• Turn off cell phones before each class.
• No textmessaging in class. No headphones. If you wish to use a laptop in
this class for purposes of note taking, that’s great, but if you are caught
playing games or browsing web sites or other non-organic activities you
will be asked to leave, or dropped from the course. During classtime
screens must be locked in the down position if you use your tablet during
class.
• No talking during class is tolerated. You will be dropped from the course.
• Tablets or laptops will be used for the class. It is the student’s
responsibility to ensure working technology at all times. The instructor will
not provide any tech support nor give exceptions for any computer
problems.
Organic Chemistry I
Chem 326
3 Credits
South Dakota School of Mines and Technology
Fall 2011
MWF 10:00-10:50
Dr. David A. Boyles
Room 319 Chemistry Bldg
Prerequisites:
Chem 112
Chem 112L
Chem 114
YOU WILL BE REQUIRED TO DRAW ON THIS MATERIAL!
GEN CHEM SUBJECT MATTER YOU MUST KNOW IN
ADVANCE OF THIS CLASS:
1. Periodic Table: Trends, common elements, spelling and
abbreviations of elements
2. Electron configurations of H, B, Al, C, N, O, S, X
3. Lewis dot configurations of elements, compounds, ions
with geometries by VSEPR
4. Nomenclature of inorganic compounds
5. Defined: Chemical structure versus chemical formula
6. Chemical structure and chemical formulae of six strong
acids
7. Chemical reactions of acids and bases when dissolved in
water
Organic Chemistry = the chemistry of carbon compounds
Chemistry = study at the molecular level of the
(1) classification,
(2) synthesis,
(3) reactions,
(4) nomenclature
(5) properties
At least 7 million organic compared with 1 million inorganic compounds.
Fuels: gasoline, kerosene, jet fuel
The foundation for further study in
Plastics and elastomers:
Chemistry
polyethylene
Biochemistry,
polypropylene
Polymer chemistry,
polystyrene
Pharmaceutical chemistry
poly(vinyl chloride)
Chemical Engineering
polycarbonates
Industrial chemistry
poly(ethylene terephthalates)
Medicine (Paracelsus, 1493polyurethanes
1591)
rubbers
Fibers:
wool, silk, leather
rayon nylon acrylates, PET
Dyes:
Pharmaceuticals:
antibacterials, antivirals, antifungals, anticancer, antiparasitic,
antifertility, antiinflammatory, antidepressants,
anticonvulsants…
Agriculture:
insecticides, fungicides, herbicides
Detergents: soaps, surfactants
Food: oils, fats, proteins, carbohydrates
Perfumes and Flavors
Organic chemistry is
pervasive in the global
economy and is a major
source of GDP of
developed nations
Chemistry is an experimental science (Robert Boyle, The Sceptical
Chemist, 1661)
Unlike philosophy which works with ideas alone to try to
understand the world,
what is under discussion in science is what actually is known to
occur in the physical world
We are not concerned with what doesn’t happen
Organic chemistry is not just a “paper exercise” but is a formal system
of knowledge grounded in what is experimentally known to occur
This two semester course concerns WHAT happens; in other words,
this course is descriptive of the world of carbon chemistry, it
DESCRIBES the world of carbon compounds
How do we describe such a world?
1. ORGANIC CHEMISTRY IS HIGHLY SYSTEMATIZED: A FORMAL
SYSTEM OF KNOWLEDGE = EVERYTHING IS ORGANIZED BY RULES
2.
To learn organic chemistry is to learn not only what can
and does happen in the world of carbon compounds,
but to learn how to represent and predict what happens
Organic chemistry uses symbolic representations of that world
you must learn:
A representation is not the reality
A map is not the territory
Representations must be learned and maps must be created; reality
does not come with labels
LOW-GRADE
BEHAVIOR =
non-thinking
behavior….
ANY DOG CAN CHASE A FRISBEE…
LOOK PASSIVELY
GAWK
▸ verb: look with amazement; look stupidly
LISTEN PASSIVELY
also known as
“zoning out” for
a reason…
….which IN CLASSROOMS is
known as…
ARE TALKED TO =
STUDENT
PASSIVITY
“IN ONE EAR AND OUT
THE OTHER”
THE TROUBLE WITH LECTURE….
THE MORE I LECTURE…THE MORE YOU WATCH and LISTEN…
THE MORE YOU ARE PASSIVE, THE MORE YOU FOOL
YOURSELF INTO THINKING YOU UNDERSTAND…SO….
THE LESS YOU STUDY…
THE LESS YOU COME TO CLASS PREPARED….
THE LESS YOU LEARN AND REMEMBER….
THE LESS COMPETITIVE YOU ARE WITH STUDENTS
ELSEWHERE….INCLUDING HERE
THE LESS EDUCATION YOU GET FOR YOUR MONEY
Make no mistake!
ORGANIC
CHEMISTRY
IS AN…
QUESTION:
HOW DO YOU EAT AN
ENTIRE ELEPHANT?
ANSWER…
ONE BITE AT A TIME
Inch by inch…anything’s a cinch!
TO COUNTERACT THE TENDENCY TO STUPID, YOU MUST
ENGAGE WITH THE TEXT OUTSIDE EVERY CLASS
PERIOD = “HOMEWORK”
DISCOVER YOUR WEAKNESSES AND THE MENTAL
HURDLES TO LEARNING ORGANIC EARLY IN THE GAME
The sooner you begin to make your first 10,000 mistakes,
The sooner you may begin to correct them. --Nicolaides
Learning formal knowledge systems takes work, intellectual work.
Intellectual work is the counterpart of manual labor.
STUDY—A NOBLE PATH TO WISDOM
L. studium "study, application,"
originally "eagerness," from
studere "to be diligent"
Diligence = Industrious
"characterized by energy,
effort, attention" (1552)
“Do, or do not. THERE IS NO ‘TRY.’
--Jedi Master Yoda
“The academic norm is that each class
period involves one hour of work in class
and two hours outside of class for every
hour in class” ---Regent Policy Manual
YOUR MILEAGE MAY VARY…
THE SOONER YOU MAKE YOUR FIRST 10,000 MISTAKES….
THE SOONER YOU MAY BEGIN TO CORRECT THEM…
Types of thinking involved in this course
1. Verbal
multisyllabic terminology
highly standardized terminology
2. Logical
chemical structures have names based on molecular features
3. Memory
organic chemistry has its alphabet(s) that MUST be committed
to memory
4. Analogical
a reaction that occurs for one compound will similarly occur for
similar compounds—allows us to predict reactions without
doing every one of them in the laboratory
LOOK FOR SIMILARITIES AMONG REACTIONS, COMPOUNDS
5. Symbolic
organic chemistry has unique symbols to describe reality
6. Abstract
Upper classmen
Take responsibility for your own learning
This course is structured to promote becoming independent
as a learner.
Active learning—not passive: work with the text
Text in 10th edition with solutions manual
Time out of class
Two hours undistracted time out of class for each hour in
class
Read and digest
17 pages each class period
Mountain reflected in lake
Concept: Knowledge comes in chunks, not bytes
Example: “Lewis Acid”—definition, examples, other types of
acids
Formal knowledge systems do not come to us on our terms
I do not give the grade, the requirements of the course
knowledge do
Organic chemistry is a rule-based system
hyphens, commas, spelling: must be done according to the
rules or it is wrong
Not about you, not about me
You are the easiest one for yourself to fool –Richard Feynman
RULES OF THE GAME
SYLLABUS
WRITE DOWN THIS LINK NOW NOW NOW:
http://boyles.sdsmt.edu/SyllabiFall2012/Chem326.htm
CONTAINS THE ANSWER TO EVERY
QUESTION I AM ASKED WHEN I REPLY
‘READ THE SYLLABUS’
EXPECT A QUIZ ON THE SYLLABUS
Attendance
Required. Period.
Makeups for school sponsored activities ONLY as per
university policy. Period.
•
No exams or quizzes given other than at scheduled
time. Period.
IF YOU WANT SOMETHING
I EXPECT THAT…
YOU REGISTER YOUR REQUEST IN PERSON AT THE
APPROPRIATE TIME
THIS IS NOT A DISTANCE CLASS, THEREFORE
1. I do not play telephone tag with students
2. I do not answer student email
3. I am not on Facebook, LinkedIN, Twitter or other
cutsey venues
4. I ABHOR handheld devices of EVERY sort
BE WHERE YOU ARE NOW, NOT SOMEWHERE
ELSE YOU AREN’T
Kant’s Categorical Imperative
"Act only according to that maxim whereby you can, at the same time, will that
it should become a universal law.“
Emmanual Kant , Grounding for the Metaphysics of Morals 1785
In other words ask yourself “What if EVERYONE did what I am now doing?”
-texted while driving
-emailed Dr. Boyles constant updates to your changing schedule
-talked out of turn
-walked on the wrong side of the hall
-went in the left door instead of the right
-ignored the speed limit
-got up out of their seat during an exam
OFFICE HOURS
BY DEFINITION ARE THE HOURS WHEN YOU MAY SEE ME
FOR PROLONGED QUESTIONS ONLY
DON’T ANNOY ME AND ASK IF YOU MAY SEE ME
DURING MY OFFICE HOURS, OKAY?? THAT’S WHAT
THE HOURS ARE FOR!
FOR SHORT QUESTIONS ON MATERIAL SEE ME IMMEDIATELY
AFTER CLASS BEFORE I GO TO MY OFFICE
Jot down questions so you don’t forget them—unless indicated I
do not take random questions in a class this large
1.
When to see me:
Office hours without appointment; Office hours are MWF 11:00 to 11:50.
THE best time to see me is immediately after class while I am yet in class if
you have quick questions--don't put them off--there will be new material
tomorrow. I handle quick questions quickly and they usually do not need
office time.
By appointment made while I am yet in class after class but only if you cannot
follow above directions.
For BRIEF questions see me immediately after class while I am yet in the
classroom.
2.
When NOT to see me:
•
•
•
3.
Immediately before class.
When I am obviously in a hurry, or when I am clearly in serious
conversation with someone else--wait your turn.
When I am with chemicals or in the laboratory.
When you MUST see me in my office and not in public:
Private matters including grades issues, medical issues, personal matters—
yours, not mine.
NOTE WELL. ETHICS
1. I DO NOT DISCUSS WITH ANY INDIVIDUAL ANY MATTER OF
CONCERN TO THE ENTIRE CLASS
If your question is in the interest of
the entire class, ask before the entire
NO INSIDER SECRETS!!
class
2. I DO NOT REPEAT WHAT I HAVE ALREADY PUT IN WRITING AND WHAT
YOU ARE GIVEN ACCESS TO—SYLLABUS, ASSIGNMENTS, OFFICE
HOURS
….to do so fosters learned helplessness on your part
3. I DO NOT ANSWER QUESTIONS BEFORE OR DURING QUIZZES
AND EXAMS
…..I want to know what YOU know, and what sense you
make of the question and the material, even if there is a
typo OR ambiguity
Everyone has the same information including typos
GRADING
Quizzes
~20%
Exams
~60%
Comprehensive ~20%
There will be
1. Pre-lecture, daily quizzes: must be taken BEFORE class
2. Chapter quizzes
3. Examinations (~2 or 3)
4. A comprehensive final over the semester will be given 2-3:50 p.m.
December 14
Approximately in this class:
A = 10%
8 students
B = 20%
16 students
C = 40%
32 students
D = 20%
16 students
F = 10%
8 students
ASSIGNMENTS AT END OF EACH
PERIOD: 1.1 TO 1.8 FOR THIS
FRIDAY
APPROXIMATELY 10-11 CHAPTERS COVERED THIS
SEMESTER
~ 550 PAGES/ 35 PERIODS = 17 PAGES/ PERIOD
KEEP IT IN PERSPECTIVE—
1.
2.
3.
WIDE MARGINS
LOTZA PICTURES
YOU HAVE SOLUTIONS TO EVERY PROBLEM-USE SOLUTIONS MANUAL and WILEYPLUS
READING--GUESS WHAT?
YOU WON’T UNDERSTAND EVERYTHING YOU READ THE FIRST TIME—
PEOPLE OVERESTIMATE THEIR INTELLIGENCE AND ABILITY
YOU WILL NOT BE ALONE—Everyone is in the same boat and
faces the same assignment and quiz
YOUR COMPREHENSION WILL IMPROVE WITH TIME AND EFFORT—
AS LONG AS YOU DO NOT PASSIVELY “READ”
3R Method
This is intellectual work—to keep your mind active and not
going on automatic and passive pilot
1. READ—do not merely
highlight
2. RECITE—ask yourself to
summarize in points what
you have read
3. REVIEW—summarize your
study session before
leaving it
(The mind is a sieve---full of holes stuff leaks out of)
1 THE BASICS: Bonding and Molecular Structure 1
1.1 We Are Stardust 2
1.2 Atomic Structure 2
1.3 The Structural Theory of Organic Chemistry 5
1.4 Chemical Bonds: The Octet Rule 7
1.5 How to Write Lewis Structures 9
1.6 Exceptions to the Octet Rule 11
1.7 Formal Charges and How to Calculate Them 13
1.8 Resonance Theory 15
1.9 Quantum Mechanics and Atomic Structure 20
1.10 Atomic Orbitals and Electron Configuration 21
1.11 Molecular Orbitals 23
1.12 The Structure of Methane and Ethane: sp3 Hybridization 25
THE CHEMISTRY OF . . . Calculated Molecular Models:
Electron Density Surfaces 29
1.13 The Structure of Ethene (Ethylene): sp2 Hybridization 30
1.14 The Structure of Ethyne (Acetylene): sp Hybridization 34
1.15 A Summary of Important Concepts that Come from Quantum
Mechanics 36
1.16 Molecular Geometry: The Valence Shell Electron Pair Repulsion
Model 38
1.17 How to Interpret and Write Structural Formulas 41
REMEMBER….
Winners are simply those ….
Who do things losers don’t
want to do
http://boyles.sdsmt.edu/SyllabiFall2012/Chem326.htm