Addition Organic Chemistry Reading from the
Web
for Organic Chemistry, Brown and Foote, Third Edition
Maintained by Steven
A. Hardinger, Department of Chemistry & Biochemistry,
University
of California Los Angeles
Read
the guest book. Sign
the guest book.
This list of selected web site links may help you with your study of
organic chemistry, expand your knowledge, and may be just plain fun to
read.
Each chapter features a "Student Favorite" web site. This site
has been nominated by students as the most useful, most instructive of
just plain most fun site for this chapter. The site with the most
votes for each chapter is listed as the Student Favorite. To
nominate
a site, send
an e-mail to Dr Hardinger, and be sure to include the chapter
number
and the URL of the site that you are nominating. The site you
nominate
may be one currently listed on this page, or can be a site not listed
here.
Some features of these web sites require the presence of various
browser
plug-ins, which may be downloaded for free by clicking on the plug-in
name:
Acrobat
Reader | Chime
| Shockwave
| Quicktime
(Mac)
To report a broken link or if you know of a good organic chemistry
web
site that is not on this list but should be please send
an e-mail to Dr. Hardinger.
Click on a chapter number to access the related url
list.
Chapter
1: Covalent Bonding and the Shapes of Molecules
Student Favorite
Featured Sites
Concept Focus Questions and Practice Problems
Tutorials
Other Sites
- Periodic Table
- Lewis Structures
- Functional Groups
- Bonding and VSEPR
- Quantum Mechanics and Orbitals
Chapter
2: Alkanes and Cycloalkanes
Student Favorite
Featured Sites
- Molecular shape is dynamic, not static. Animations can
emphasize
this concept. Examine these molecular movies of ethane and butane
carbon-carbon bond rotation. http://www.molecules.org/movies.html
- Conformation is now widely recognized as having significant
influence
on
the chemical, physical and biological properties of organic
compounds.
The 1969 Nobel Prize in Chemistry was awarded to Derek H. R. Barton and
Odd Hassel "for their contributions to the development of the concept
of
conformation and its application in chemistry." http://www.nobel.se/chemistry/laureates/1969/index.html
Concept Focus Questions and Practice Problems
Molecular
Dynamics
Other Sites
Chapter 3:
Chirality
Student Favorite
Featured Sites
- Around 1874, Joseph LeBel and Jacobus van’t Hoff independently
proposed
that carbon with four attachments assumes a tetrahedral geometry, and
that
if these four attachments were different, the compound should have two
isomers. Read LeBel’s paper in which he outlines these ideas. http://www.dbhs.wvusd.k12.ca.us/Chem-History/LeBel-1874.html
Concept Focus Questions and Practice Problems
Stereochemistry
Tutorials
Other Sites
- Theory and Tutorials
- Vocabulary
- Louis Pasteur
- Chirality, Drugs and Biology
Chapter 4:
Acids and Bases
Student Favorite
Featured Sites
- Acid-base chemistry is fundamental to understanding many aspects
of
organic
reactivity. Tables of pKa values are thus
valuable
to anyone studying organic chemistry. There are many such tables
available, such as this table from the excellent organic chemistry
hypertext
of William Reusch (Michigan State University). http://www.cem.msu.edu/~reusch/OrgPage/acidity2.htm
- Carbocations were proposed as intermediates in organic reactions
in the
early part of the 20th century, but their existence was not
definitively
shown until the 1960’s by George Olah (University of Southern
California).
This work was recognized with the 1994 Nobel Prize in Chemistry. http://www.nobel.se/chemistry/laureates/1994/press.html
Concept Focus Questions and Practice Problems
Organic
Acids and Bases
Tutorials
Acids
and Bases
Carbocations
Other Sites
Chapter 5:
Alkenes
I
Student Favorite
Featured Sites
Other Sites
Chapter 6:
Alkenes
II
Student Favorite
Featured Sites
- Transition state define many aspects of chemical reactions, yet
their
extremely
short lifetimes (one femtosecond, the duration of a single bond
vibration)
makes them exceptionally difficult to observe. Ahmed Zewail
(CalTech)
was awarded the 1999 Nobel Prize in Chemistry for "his studies of the
transition
states of chemical reactions using femtosecond spectroscopy." http://www.nobel.se/chemistry/laureates/1999/
- A typical bromonium ion is reactive and has but a fleeting
existence.
An exception was found in the reaction of the sterically hindered
alkene
adamantylideneadamantane with Br2, providing a bromonium ion
that was isolated and characterized. http://www.pharmacy.purdue.edu/~mcmp204/MOW/week2/MOW.html
- Hydroboration is among the most important organic reactions for
both
laboratory
and industrial organic synthesis. The 1979 Nobel Prize in
Chemistry
was shared by Herbert Brown (Purdue University) for "development of the
use of boron....containing compounds into important reagents in organic
synthesis." http://www.nobel.se/chemistry/laureates/1979/press.html
- Carbocations were proposed as intermediates in organic reactions
in the
early part of the 20th century, but their existence was not
definitively
shown until the 1960’s by George Olah (University of Southern
California).
This work was recognized with the 1994 Nobel Prize in Chemistry. http://www.nobel.se/chemistry/laureates/1994/press.html
Concept Focus Questions and Practice Problems
Addition
to Carbon-Carbon p Bonds
Tutorials
Carbocations
Other Sites
- Alkene Reactions and Mechanisms
- Miscelleneous Topics
A
Conversation with... Carl Djerassi
Student Favorite
Featured Sites
Chapter
7: Haloalkanes, Alkenes and Arenes
Student Favorite
Featured Sites
- Halogenated hydrocarbons are common laboratory solvents, with a
variety
of chemical and physical properties. Solvent properties are
critical
in efficient isolation of pure organic compounds from biological
materials.
Read about how dichloromethane helped solve a mystery of aggressive
birds
and poisoned shellfish. http://antoine.frostburg.edu/chem/senese/101/features/domoic.shtml
- CFCs pose a significant threat to the ozone layer due to radical
chain
reactions. Learn more about ozone hole science at The Ozone Hole
Tour. http://www.atm.ch.cam.ac.uk/tour/
- Nitric oxide (NO) is a biological messenger molecule and free
radical.
The 1998 Nobel Prize in Physiology or Medicine was awarded to Robert
Furchgott
(SUNY, Brooklyn), Louis Ignarro (UCLA) and Ferid Murad (University of
Texas,
Dallas) "for their discoveries concerning nitric oxide as a signaling
molecule
in the cardiovascular system" http://www.nobel.se/medicine/laureates/1998/
Concept Focus Questions and Practice Problems
Radicals
Other Sites
- Reactions and Mechanisms
- Halocarbons and Radicals in the Environment
- Halocarbons and Radicals in Biology
- Applications of Halocarbons
Chapter
8: Nucleophilic Substitution and β-Elimination
Student Favorite
Featured Sites
Concept Focus Questions and Practice Problems
Tutorials
Other Sites
- Kinetics, Thermodynamics and Transition State Theory
- Ionic Substitution Reactions
- b-Elimination Reactions
- Carbocations
- Solvents
- Miscelleneous Topics
Chapter
9: Alcohols and Thiols
Student Favorite
Featured Sites
Concept Focus Questions and Practice Problems
Alcohols
and Ethers
Other Sites
Chapter 10:
Alkynes
Student Favorite
Featured Sites
- Elias J. Corey (Harvard), a pioneer in organic synthesis, is
credited
with
the concept of retrosynthesis. He was awarded the 1990 Nobel
Prize
in Chemistry for "his development of the theory and methodology of
organic
synthesis." http://www.nobel.se/chemistry/laureates/1990/
- Organic synthesis is as much art as science, but it need not be
overwhelming.
Approach it logically! To see one person’s thoughts on the
subject,
read "How to Tackle Organic Synthesis: A Beginner's Guide." http://orac.sunderland.ac.uk/~hs0bcl/org1.htm
Concept Focus Questions and Practice Problems
Addition
to Carbon-Carbon p Bonds
Chapter
11: Ethers, Sufides and Epoxides
Student Favorite
Featured Sites
- Technetium is useful for medical imaging, and is present in spent
nuclear
reactor fuel rods and other radioactive waste, but is not present in
any
natural ores. Read about a novel process which employs crown
ethers
for removing technetium from radioactive wastes. http://www.ornl.gov/divisions/casd/csg/highlights/srtalk.html
- Valinomycin in a polypeptide ionophore antibiotic that forms a
potassium
cation complex. This complex can then move across a cell
membrane,
killing the bacterium. Visit this web site to see an interactive
model of the valinomycin-potassium complex. http://www.soils.wisc.edu/virtual_museum/valinomycin/
Concept Focus Questions and Practice Problems
Alcohols
and Ethers
Other Sites
Chapter
12: Infrared Spectroscopy
Student Favorite
Featured Sites
- Absorption and reflection of solar infrared radiation is the
cause of
global
warming and the greenhouse effect. The intensity and wavelength
of
infrared energy reflected or absorbed is a function of molecular
structure. http://www.whrc.org/globalwarming/warmingearth.htm
Concept Focus Questions and Practice Problems
Infrared
Spectroscopy
Other Sites
- Theory and Tutorials
- Collections of IR Spectra
- Applications of IR Spectroscopy
- Collections of Problems to Solve
- Miscellaneous Sites
A
Conversation with...Jacquelyn Gervay-Hague
Student Favorite
Featured Sites
Chapter
13: Nuclear Magnetic Resonance Spectroscopy
Student Favorite
Featured Sites
- Richard Ernst (ETH, Zurich) was awarded the 1991 Nobel Prize in
Chemistry
for "his contributions to the development of the methodology of high
resolution
nuclear magnetic resonance (NMR) spectroscopy." http://www.nobel.se/chemistry/laureates/1991/
- Chemical shifts can be estimated. Here is an example of an
aliphatic
proton chemical shift predictor. It can be used to explore trends
in the relationship between functional groups and chemical shifts. http://www.colby.edu/chemistry/NMR/H1pred.html
- NMR theory can be complex, but out of that complexity rises a
host of
useful
NMR techniques. Explore a more detailed theoretical explanation
of
NMR at this web site. http://www.cis.rit.edu/htbooks/nmr/
- Logical thinking, persistence and practice are the keys to
solving
spectral
problems. Here are some comments on problem solving strategy, as
well as some IR and NMR spectral problems for more practice. http://www.chem.ucla.edu/~webspectra/
Concept Focus Questions and Practice Problems
Other Sites
- Theory and Tutorials
- Collections of Spectra
- Collections of Problems to Solve
- Magnetic Resonance Imaging (MRI)
- NMR
and MRI: Chester F. Carlson Center for Imaging Science, Rochester
Institute
of Technology
- Miscellaneous Sites
Chapter
14: Mass Spectrometry
Student Favorite
Featured Sites
- Mass spectrometry is among the oldest instrumental methods in
chemistry.
Its use lead to several major discoveries, such as the existence of
isotopes.
Read more about the history of mass spectrometry. http://masspec.scripps.edu/hist.html
Concept Focus Questions and Practice Problems
Other Sites
- Theory and Tutorials
- Collections of Mass Spectra
- Collections of Problems to Solve
- Related Nobel Prizes
- Applications of Mass Spectrometry
- Miscellaneous Links
Chapter
15: Organometallic Compounds
Student Favorite
Featured Sites
- The Organometallic Hypertext Book is an excellent resource for
further
reading on many aspects of transition metal organometallic chemistry. http://www.ilpi.com/organomet/
Other Sites
Chapter
16: Aldehydes and Ketones
Student Favorite
Featured Sites
Concept Focus Questions and Practice Problems
Other Sites
- Nomenclature
- Theory and Mechanisms
- Aldehydes and Ketones in Biology
Chapter
17: Carboxylic Acids
Student Favorite
Featured Sites
- The Monsanto acetic acid process is an excellent example of
transition
metal catalysis on an industrial scale. Read more about this
reaction
in the Organometallic HyperTextBook. http://www.ilpi.com/organomet/monsanto.html
Concept Focus Questions and Practice Problems
Other Sites
- Acidity of Carboxylic Acids
- Theory and Mechanisms
- Carboxylic Acids in Biology
- Applications of Carboxylic Acids
Chapter
18: Functional Derivatives of Carboxylic Acids
Student Favorite
Featured Sites
Concept Focus Questions and Practice Problems
Other Sites
A
Conversation with...Roald Hoffmann
Student Favorite
Featured Sites
Chapter
19: Enolate Anions and Enamines
Student Favorite
Featured Sites
- Sir William Henry Perkins is considered the father of the modern
dye
industry
due to an accidental discovery while trying to synthesize the
antimalaria
drug quinine. He also developed the Perkin reaction, a useful
route
to b-aryl-a,b-unsaturated
carboxylic acids. http://www.chemheritage.org/perkin/Perkin/perkin.html
- Conjugate addition of a radical to an a,b-unsaturated
ester is the key mechanism step in the polymerization of methyl
methacrylate
to form poly(methyl methacrylate), also known as Plexiglas or Lucite. http://www.psrc.usm.edu/macrog/pmma.htm
Concept Focus Questions and Practice Problems
Other Sites
Chapter
20: Aromatics I: Benzene and Its Derivatives
Student Favorite
Featured Sites
- The study of molecular orbitals is critical to modern organic
chemistry.
Orbital considerations often provide a more rigorous explanation than
simpler
concepts. Consult this web site for a more detailed introduction
to molecular orbital theory. http://origin.ch.ic.ac.uk/vchemlib/course/mo_theory/
Concept Focus Questions and Practice Problems
Introduction
to Aromaticity
Conjugation
and Molecular Orbital Theory
Other Sites
Chapter
21: Aromatics II: Reactions of Benzene and Its Derivatives
Student Favorite
Featured Sites
- Aromatic nitration provides 2,4,6-trinitrotoluene (TNT).
Packing
many nitro groups into a small space increases explosive power.
Octanitrocubane
has recently been synthesized, and studies show this molecule has
explosive
potential. http://www.sciencenews.org/20000122/fob6.asp
- Hermann Müller discovered the insecticidal activity of DDT,
and
was
awarded the 1948 Nobel Prize in Physiology or Medicine for "his
discovery
of the high efficiency of DDT as a contact poison against several
arthropods."
DDT proved to be a toxic to birds, and was banned less than 40 years
after
Müller's Nobel Prize was awarded. http://www.nobel.se/medicine/laureates/1948/press.html
Concept Focus Questions and Practice Problems
Other Sites
Chapter 22: Amines
Student Favorite
Featured Sites
Concept Focus Questions and Practice Problems
Amines
Other Sites
Chapter
23: Conjugated Systems
Student Favorite
Featured Sites
Concept Focus Questions and Practice Problems
Conjugation
and Molecular Orbital Theory
Pericyclic
Reactions
Other Sites
A
Conversation with... Paul S. Anderson
Student Favorite
Interchapter
Student Favorite
Featured Sites
Concept Focus Questions and Practice Problems
Organic
Chemistry of Pharmaceuticals
Other Sites
Chapter
24: Organic Polymer Chemistry
Student Favorite
Featured Sites
Chapter 25:
Carbohydrates
Student Favorite
Featured Sites:
Concept Focus Questions and Practice Problems
Other Sites
The
Carbohydrate Resource
Chapter 26: Lipids
Student Favorite
Featured Sites
Concept Focus Questions and Practice Problems
Lipids
Chapter
27: Amino Acids and Proteins
Student Favorite
Featured Sites
- Tertiary structure is critical to understanding protein
biochemistry
and
drug design, yet predicting this structure from the amino acid sequence
is an enormous challenge. Read about Protein Folding: Background,
Importance and Prediction. http://bioinfo.mshri.on.ca/trades/trajhome.htm
Concept Focus Questions and Practice Problems
Amino
Acids, Peptides and Proteins
Other Sites
Chapter 28:
Nucleic Acids
Student Favorite
Featured Sites
Concept Focus Questions and Practice Problems
Nucleic
Acids
Other Sites
Chapter
29: The Organic Chemistry of Metabolism
Student Favorite
Featured Sites
Other
Chemistry
Link Portals
Student Favorite
Other Sites
- Organic
Chemistry, Linda Sweeting, Towson University
- ChemConnections:
A New Approach to Teaching Chemistry at UC Berkeley
- Study
Aids in General
and Organic Chemistry
- University
of Liverpool
- General,
Organic and Biochemistry
- The
Chemistry Hypermedia Project
- Global
Instruction
Chemistry
- Institute
of Chemistry: Chemistry Index
- Molecules
from Chemistry
- Web-sters
Organic Chemistry
- Organic
Chemistry Resources Worldwide
- CFCC
Organic
Chemistry List
- Ron
Rinehart's Chemistry Web Resources Content Organizer
- Carl
Wamser
List
- OnLine
Course
Materials
in General and Organic Chemistry
- Chemfinder
- Properties, Structures, Etc. of 75,000+ Unique Substances
- Organic
Syntheses
Website
and Database
- Educational
Materials for Organic Chemistry
- Organic
Chemistry Resources
- World
Index of Molecular Visualization Resources
- Liz
Dorland's Chemistry Page
- Organic
Chemistry Toolkit
- Links
for Chemists
- The
Chemist's
Art Gallery
- The
Catalyst: Chemistry Education Resources for the Secondary School
teacher
on the WWW
- Selected
Classic Papers from the History of Chemistry
- Colby
College O-Chem Links Page
- Organic
Chemistry Help eMediately
- Some
Interesting WWW Sites Related to the Introductory Chemistry Laboratory
- WWW
Links
- Organic
Chemistry Resources
- Dr.
Glaser’s Portal to Organic Chemistry Destinations on the World Wide Web
- Organic
Chemistry Links
- Global
Chemistry Links
- Organic
Chemistry On Line (Paul Young)
- General,
Organic, and Biochemistry (James K. Hardy and West Publishing
Company)
- Chemistry
Index (Freie Universitaet, Berlin) More chemistry links around the
world; German and English.
- Molecular
Playground
(Cabrillo University) Molecular modeling, molecules in the news,
molecules
to explore.
- CHEMystery
A quick review of some basic general and organic chemistry topics such
as electrochemistry and functional groups.
Course
Pages
and Tutorials
Student Favorite
Virtual
Textbook of Organic Chemistry An
organic
chemistry textbook on line!
Other Sites
Chemical
Structure Drawing Software