•  What is Organic Chemistry?
❏ 
Wikipedia definition: "Organic chemistry is a discipline within chemistry which
involves the scientific study of the structure, properties, composition, reactions,
and preparation (by synthesis or by other means) of chemical compounds that
contain carbon.”
❏  Carbon
is the third most abundant element in the universe
after hydrogen and oxygen respectively.
❏  Pure carbon is an allotrope, i.e., in its crystalline state it can
exist in different forms with different atomic arrangements and
different physical/chemical properties.
❏  Some of the allotropic forms of carbon are: graphite,
graphene, fullerene and diamond.
Carbon Allotropes: Graphite
Carbon Allotropes: Graphene
Graphite is layered. In each layer, the carbon
atoms are arranged in a hexagonal lattice.
vs.
graphite
Graphite is commonly used in “lead” pencils,
which is a misnomer.
http://wikipedia.org
Carbon Allotropes: Buckminsterfullerene
(IUPAC name (C60-Ih)[5,6]fullerene)
• Truncated icosahedron
• Twenty hexagons and twelve pentagons
• The 6:6 ring bonds (between two hexagons) can be
considered "double bonds" and are shorter than the 6:5
bonds (between a hexagon and a pentagon). Their
average bond length is ≅ 0.148 nm.
http://wikipedia.org
• Graphene is a one-atom-thick planar sheet of sp2-bonded
carbon atoms that are in a hexagonal arrangement in a
honeycomb crystal lattice.
• The bond length in graphene is ≅ 0.142 nm. • It behaves as a semi-metal and semiconductor.
• It is presently one of the most expensive materials on
Earth. A sample the size of a cross section of a human hair
has a cost of more than $1,000. http://wikipedia.org
Carbon Allotropes: Diamond
• Transparent crystal of tetrahedral sp3 hybridized
carbon atoms with bond lengths > 0.148 nm
• Crystal lattice is a variation of a face centered cubic
structure
• Formed at high-pressure and high-temperature
• Hardest material known, slows light traveling in a
vacuum by ≅ 40% http://wikipedia.org
1
Organic Chemistry
❏  …….. is a discipline within chemistry which involves the
scientific study of the structure, properties, composition,
reactions, and preparation (by synthesis or by other means) of
chemical compounds that contain carbon.
2. 
How many different arrangements of carbon &
hydrogen atoms (framework patterns/structural
backbones/ shapes) are found in the published
organic molecules?
http://www.chm.bris.ac.uk/sillymolecules/sillymols.htm
1. Approximately how many compounds that contain carbon
have been published in the scientific literature to date?
A. 100,000
B. 1,000,000
C. 10,000,000
D. 100,000,000
E. 1,000,000,000
3. How many different single and multi-step reactions
have been published?
A. 100
B. 1,000
C. 10,000
D. 100,000
E. 1,000,000
A. 100
B. 1,000
C. 10,000
D. 100,000
E. 1,000,000
The names of many
organic molecules tend to
be unique.
4. What is the general stoichiometry (mole ratios of a
and b respectively) of the reactants A & B in > 95%
of all organic reactions?
aA + bB → product(s)
A. 2:1
B. 3:2
C. 1:1
D. No idea.
How old is organic chemistry as a science?
5. How old is organic chemistry as a science?
A.  5,000 years old
B.  1,000 years old
C.  500 years old
D.  200 years old
E.  50 years old
❏  Separation
& Purification: distillation, recrystallization,
chromatography (3000 B.C. to present)
❏  Ancient view: "Living = Organic" vs. Inanimate = Inorganic
❏  Urea, Vitalism & Friedrich Wohler, Ann. Physik: 122, 253
(1828)
❏  Formulas & "Functionality", Wurtz (1849)
❏  Synthesis: Kolbe [alcohols], Williamson [ethers], Baeyer
[aspirin], (1850)
❏  Kekule's Snake (1857-58) ❏  Graphic Formulas (Couper, Butlerov; 1861)
❏  Lewis Structures /G.N. Lewis, J. Amer. Chem. Soc., 38, 762
(1916)
❏  Spectroscopy: IR, UV, NMR, MS, (1920 to present)
2
6. Which undergraduate majors other than chemistry and chemical
engineering require undergraduate courses in O-Chem?
❏ 
❏ 
❏ 
Pre-med, biological, plant, animal, life, forensics, and some environmental
& “non-science” majors.
Any of you psychology majors?
Middle/ secondary education majors?
7. Where does Organic Chemistry fit in your career plans, and how
can you usefully apply the knowledge that you develop?
❏ 
Only you can answer these questions.
8. What do you plan to do in this course to meet your goals and
expectations?
❏ 
❏ 
Only you can answer this question.
Memorize, memorize, memorize….??
~24,000,000 compounds
~800,000 different shapes
~14,000,000 reactions
Not a good idea?
Pre-class / In-class / Tests:
1.  Prepare before each class by consulting the on-line presentation
links from the course calendar Web page, preview the
corresponding sections in the Carey textbook, prepare answers to
the embedded questions. (These will be used with your i-clicker
during each class.) Come to every class.
2.  Practice using the key concepts as soon as possible after the
material is covered by working on the Webassign questions
(individually), Worksheets (collaboratively), and ACS questions
(individually and collaboratively); stay current with new
information and concepts with practice on a daily basis.
3.  Keep information simple and memorization to a minimum; trust
your logic; find useful metaphors; focus on molecular patterns.
Your understanding & confidence will build, and it will be easier
than cramming before test day. Learn to take tests.
General Chemistry Topics: (To be expanded and thoroughly covered.)
Atomic & Molecular Structure
•  Empirical & Molecular Formulas
•  Structural Formulas
•  Lewis or Bond Line
•  Condensed
•  Line or Line-Angle or Skeletal or Stick or Wire
•  3-dimensional (VSEPR)
What do you need to do in this course to meet Dr. R.’s
expectations? (Are his different than mine?)
Dr. R.’s: Have a clear understanding of and be able to apply
fundamental concepts./ Master hands-on skills. / Score well in
tests.
Laboratory:
1.  Develop safe, efficient, and hygienic operational skills;
2.  Provide unambiguous, succinct, and clear records (lab notebook)
and personal communications (written & oral reports)
3.  Deliver products (compounds in vials: synthetic, isolated,
purified);
4.  Demonstrate an understanding of the relationship of the “real”
world of hands-on chemical handling & reactions to theoretical
notions of molecules, structures. (A most important bridge with
class lectures.)
• 
• 
• 
• 
• 
• 
• 
• 
Important General Chemistry Topics:
(Many of these MUST be mastered.)
Atomic & Molecular Structure
Carbon, Hydrogen, Nitrogen, Oxygen (Sulfur, Phosphorus and
the Halogens)
Electron Configurations / Atomic s and p Orbitals
Octets, Expanded Octets
Molecular Orbitals
Hybridization/ Molecular Shape
Forces between atoms / Ionic & Covalent Bonding / Lewis
Structures (Bonded / Non-bonded electrons)
Using the Periodic Table / Atomic Size, electronegativity, valence,
& other properties
Bond Types / Covalent; Ionic; Hydrogen; Others
General Chemistry Topics: (To be expanded and thoroughly covered.)
Acids & Bases
• 
Definitions: Arrhenius, Brønsted, Lewis
• 
Organic Acids & Bases
• 
Strength, pH, pKa, pKb / Relative Strengths
• 
Reactivity
http://chemconnections.org/COT/organic1/VSEPR/
• 
Resonance
• 
Polarity & Formal Charge
Organic Functions
• 
3
http://chemconnections.org/organic/Movies%20Organic/Representations.mov
http://chemconnections.org/COT/organic1/VSEPR/2B-jmol.html
1930 - 1996
1920
What is bombykol’s molar mass?
1920
1920
http://upload.wikimedia.org/wikipedia/commons/7/73/TwinPeaksDepthAdjusted.jpg
http://www.3dchem.com/molecules.asp?ID=34
http://www.3dchem.com/molecules.asp?ID=305
http://www.senseofsmell.org/scientific-articles-pheromones.php
4
http://www.3dchem.com/molecules.asp?ID=305
Taxotere (docetaxel)
Taxus baccata
Cancer chemotherapy (~$2bn/yr)
Protein Shape: Forces, Bonds, Self Assembly,
Folding
10-40kJ/mol
Molecular Shapes?
http://www.personal.kent.edu/~cearley/PChem/jmol/collagen.htm
150-1000kJ/mol
700-4,000kJ/mol
Ion-dipole
(Dissolving)
40-600kJ/mol
0.05-40kJ/mol
Streptococcus pyogenes
96,000 x
Vincent A. Fischetti Ph.D., Rockefeller University
http://chemconnections.org/Presentations/Columbia/slide8-3.html
5
Returning to a very important question.
What do you plan to do in this course to meet your goals and
expectations? (Self Perceived Abilities)
A) not that much; I'm very "smart" with an IQ > 140; chemistry & science
come easily to me.
B) lots and lots since I'm not as "smart" as I would like to be, and chemistry is a
real challenge to me.
C) enough to develop solid skills by practicing everyday.
D) cram, cram, cram before each quiz, exam, and the final.
E) more than one of the above.
Self-perceived abilities (SPA), motivation and self-confidence ~50% nature ~50%
nuture: Psychological Science (May 2009)
Practice is more important than natural abilities: Intelligence (September 2007)
Ritalin
β-Blocker
Pain Relief
Provigil
12719419112001
MDMA
Learning styles and study approaches to Organic Chemistry:
http://chemconnections.org/organic/chem226/Labs/learning.html
Syllabus/Course Homepage:
http://chemconnections.org/organic/chem226/
6