01:160:307 Lecture Notes - Lecture 1: Lewis Structure, Nonmetal, Pi Bond
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ORGANIC CHEMISTRY 307
Fall 2017
Lecture Notes I
Intro and Chapter 1
R. Boikess
Welcome to Chemistry 307, Organic Chemistry:
Be sure you understand the organizational and administrative aspects
of the course. Refer to the Sakai course site for the Syllabus, the Course
Information Document, and other documents that explain the use of the i-
clicker, the online instructional support (OWL, eBook) and Chem Draw.
These documents may be found in the Miscellaneous folder in Resources.
How to Succeed in Organic Chemistry
Much of the emphasis in General Chemistry is on numerical problem
solving. To a large extent your results in that course were determined by
your problem solving skills.
The emphasis in Organic Chemistry is on different active skills. Because the
exams are not multiple choice to any significant extent, you will need to be
able to do things to succeed.
1. The first few weeks are the key to success. So start immediately Learn
to understand and write [active skill] the different representations of organic
compounds [almost by reflex]. How? Practice
2. Develop a method for systematic memorization [flash cards or whatever
you are comfortable with]
3. Here is a recommended strategy. The lecture notes should be your first
point of attack. They tell you what is important and what approach we are
going to use. They won’t always parallel your textbooks. Read them before
you read the textbooks. Do not read the book until after you have read the
relevant lecture notes. Then read the assignments in the textbooks before the
lectures, focusing on the things that are emphasized in the lecture notes.
Come to lectures, then reread the textbooks and the notes, do the homework,
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much of which is on line, and do not look at the solutions in the solutions
manual or in CP until you have given it your all. Remember, it’s not enough
to understand the answer. You must also master the skills that lead to the
answer. Looking at a structure and “understanding” it, is not the same thing
as being able to draw the structure.
4. In addition to the assigned homework, you will find some explanations
and a large number of additional problems (some with solutions, all with
answers) in a folder called “How to Solve” in the Resources section of the
Sakai site. This material covers primarily the early part of the course and is
from a manuscript for a possible book called “How to Solve Organic
Chemistry Problems.” There are likely still some errors in this material. If
you find one, please bring it to my attention. Your help will be appreciated
and noted.
5. Make sure your knowledge is active; success depends on skills such as
drawing structures, assigning names, writing reaction mechanisms,
formulating synthetic routes, interpreting spectra, etc. Exams will have
questions that require hand written answers. Typical questions will start with
“Draw the structures of…” or “Give the names of…” or “Write the
mechanism of …” or “ Propose a synthesis of ….” There will be a very
small number of multiple guess questions. The Sakai site has the exams from
the six previous years posted. You will notice that the exams are similar
from year to year. They are an extremely valuable study tool. You can use
them most effectively by taking an exam under testing conditions (90
minutes in a quiet room) and then using the key to grade your paper.
6. Use recitations, review sessions, office hours, email, Facebook, etc. to
get help and answers to your questions. We are committed to providing you
as much help as possible.
7. Before exams, solve the large number of practice problems that we will
send you, work out the exams from previous years, focus on and review the
material covered in the lecture notes.
Introduction
A. What is Organic Chemistry and why do we spend at least a whole year
studying it? Think about all the different substances you encounter every
day. Almost every single one is an organic substance. Look around.
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1. Organic chemistry is often defined as the chemistry of compounds of
carbon, [oversimplified all organic compounds contain carbon, but not all
compounds that contain carbon are organic.] To some extent definitions such
as these are arbitrary or historical. We shall use this one: Organic
compounds all have at least one C-H bond, except for a very few that have
only a C-C bond or a C-X bond(X conventionally means halogen). So
compounds such as sodium bicarbonate or calcium carbonate are not defined
as organic compounds. But compounds such as carbon tetrachloride CCl4 (4
–Cl bonds) or oxalic acid, C2O4H2 (1 C-C bond) are.
Most of the organic compounds we will consider in this course consist of
only nonmetals. There is, however, a large important branch of organic
called organometallic chemistry, in which the organic compounds also
contain at least one metal atom. We shall briefly look at some
organometallic compound because of their importance in the synthesis of
other organic compounds.
2. To some laypersons, organic chemistry has a different connotation,
related to “organism” or life. This connotation is mostly historical and
comes from the fact that virtually every chemical of life is organic, one
reason why Organic Chemistry is required for majors in the life sciences.
3. Historical: The Vital Force Theory, which postulated that any substance
from a living thing had a special, almost magical ingredient called Vital
Force, was abandoned in the 19th century. The first in a series of key
experiments that led to its abandonment was the preparation of urea from
apparent inorganic sources. This urea was indistinguishable from urea from
animals, as far as Wohler (who did the experiment) could tell. But the
difficulty of proving that something doesn’t exist is the reason that it took
many more experiments and many years before everyone was finally
convinced that there was no magical, mysterious substance associated with
living things. Therefore all samples of a given pure organic substance are
the same regardless of their origin. A pure synthetic vitamin is the same as a
pure natural one.
4. Most known chemical compounds are organic. There are more than 100
million chemical substances known, most of them organic. That number is
increasing every day. (50 years ago there were fewer than 1 million) In
addition there are over 66 million genetic sequences known. Technically,
each one is a different organic compound.
B. What’s so special about Carbon? Why are there so many compounds of
Carbon? Review the material on the Periodic Table, the electronic
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Document Summary
Be sure you understand the organizational and administrative aspects. Welcome to chemistry 307, organic chemistry: of the course. Refer to the sakai course site for the syllabus, the course. Information document, and other documents that explain the use of the i- clicker, the online instructional support (owl, ebook) and chem draw. These documents may be found in the miscellaneous folder in resources. Much of the emphasis in general chemistry is on numerical problem solving. To a large extent your results in that course were determined by your problem solving skills. The emphasis in organic chemistry is on different active skills. Because the exams are not multiple choice to any significant extent, you will need to be able to do things to succeed: the first few weeks are the key to success. So start immediately learn to understand and write [active skill] the different representations of organic compounds [almost by reflex].
