Curriculum Map

Organic Chemistry

Author:
Rebecca DeVasher, Associate Professor, Rose-Hulman Institute of Technology, Terre Haute, Indiana

This Curriculum Map provides a list of highly relevant and engaging content from throughout AccessScience for use in enriching your teaching. Site assets such as tables, graphs, diagrams, photos, and animations have been mapped to standard topics taught in an introductory Organic Chemistry course. Use the "Copy Link" functionality to paste a direct link from each asset into your school's learning management system for easy incorporation into your curriculum.

Course Topics

Structure and Function in Organic Chemistry
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Table The principal organic functional groups are repeating combinations of bonded atoms that occur in organic molecules. This table from the Organic chemistry article displays some of the principal functional groups and their structures. copy link
Table We can classify functional groups according to their bonding types and atoms. This table from the Organic nomenclature article exemplifies the naming of compounds containing functional groups. copy link
Biography John Newlands recognized the importance of systematic nomenclature for communicating structural information about chemical species. copy link
Research Review One of the basic tenets of drug design is that the biological activity of a drug is dependent on the 3D placement of its specific functional groups. This article explains why molecular modeling for drug design focuses on interactions between functional groups of biologically active molecules, biochemical enzymes, and other chemical messengers that carry out biological functions. copy link
Article The most common organic compounds have systematic nomenclature. This brief article on caffeine provides the systematic name for this compound, along with its structural formula. copy link
Article Section This section of the Stereochemistry article explains the concepts of symmetry and chirality in molecular structures. copy link
Article Tartaric acid is a naturally occurring meso compound. It represents a special class of compounds that possess chiral centers and a plane of symmetry. This brief article describes the stereochemical configurations of tartaric acid. copy link
Diagram The two mirror images of naproxen, shown in the Asymmetric synthesis article, illustrate one type of molecular isomerism. These compounds are enantiomers of one another, meaning that they are non-superimposable mirror images. copy link
Biography Vladimir Prelog was one of the preeminent individuals that developed rules for classifying the directionality of a chiral center. copy link
Alkanes, Alkenes, and Alkynes
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Diagram This figure from the Structural chemistry article presents various examples of saturated hydrocarbons, otherwise known as alkanes. copy link
Table This table from the article on alkanes shows the nomenclature and properties of several important compounds. copy link
Graph This potential energy diagram for the conformational changes of the alkane butane shows how energy fluctuates with strain placed on the molecule as the bond angles accommodate various movements of butane's molecular structure. copy link
Article This article on molecular mechanics introduces the concept of molecular modeling, which takes into account the various conformations that a molecule can assume. It can help promote the understanding of conformational changes associated with alkanes. copy link
Diagram This diagram from the article on alkenes illustrates the molecular orbital of double-bonded carbon atoms. copy link
Reaction The hydroboration reaction represents one route toward alcohols from alkenes. This reaction can also be used to make aldehydes through a similar, and indirect, addition of water to alkynes. copy link
Article section Acetylene, the simplest alkyne, undergoes addition to produce many valuable materials and precursors. This section of the Acetylene article lists some of its many uses. copy link
Article section This section of the article on alkynes shows several useful addition reactions. copy link
Reactions of Alkyl Halides and Alcohol
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Article section This section of the Halogenated hydrocarbon article describes the preparation and reactions of alkyl halides. copy link
Table Alcohols, like alkyl halides, are an important class of reactive organic functional groups that provide chemists with the precursors to many other compounds. This table classifies some alcohols by their common name, IUPAC name, and chemical formula. copy link
Research Review Fluorinated organic compounds are profoundly different in both physical and chemical properties from their non-fluorinated analogs. Fluorination can be achieved through nucleophilic substitution reactions, such as the ones described in this 2013 Research Review. copy link
Article The concept of atom economy, as this article describes, embodies the principles of green chemistry. In an effort to reduce or eliminate waste, atom economy attempts to avoid the by-products inherent in substitution processes. copy link
Resonance and Conjugated Systems
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Article section This section of the Resonance article differentiates this feature from equilibration. copy link
Animation This detailed animation of electron delocalization uses the Lewis structure of ozone to explain the resonance phenomenon. copy link
Article section An example of resonance in the benzene structure is shown in this section of the Aromatic hydrocarbon article. copy link
Article Conjugated systems have unique chemical and physical stability that impart significant advantages in terms of their use in practical applications. This article, entitled Conjugation and hyperconjugation, uses quantum mechanics to explain their molecular interactions. copy link
Video Biography In this video, K.C. Nicolaou explains why organic chemistry is a lot like cooking. Nicolaou's work in conjugated systems total synthesis has led to manufacture of many important antibiotics, such as vancomycin. copy link
Biography Otto Diels worked with Kurt Alder (see below) to discover the Diels-Alder reaction—one of the most synthetically efficient and stereoselective reactions in all of organic chemistry. copy link
Biography Together with Otto Diels (see above), Kurt Alder won the 1950 Nobel Prize for Chemistry for deriving the Diels-Alder reaction. copy link
Reactions The Diels-Alder reaction uses only the reactants and heat to produce a cyclic compound that contains all of the atoms from the reactants to form a single product. Two examples of this reaction are shown here. copy link
Aromatic Compounds
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Biography Kekulé von Stradonitz determined the so-called ring structure of benzene through repeated reactions of this hydrocarbon with reagents known to affect color change in isolated and linear alkenes. Because those reactions did not occur with benzene, Kekulé made the first steps toward identifying the resonance stabilization energy associated with benzene and other aromatic compounds. copy link
Table The table in the Benzene article provides common nomenclature associated with this hydocarbon's derivatives. copy link
Biography Charles Friedel successfully combined his interests in chemistry and minerals to produce the Friedel-Crafts reaction, as this biography explains. copy link
Reaction The Friedel-Crafts reaction is one of the most widely used electrophilic aromatic substitution reactions. The product of this reaction is an alkyl benzene, as shown here. copy link
Synthetic Organic Chemistry and Organic Structure Determination
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Article This article on epoxide outlines the preparation, reactions, and uses of ethylene oxide—an important building block in organic synthesis. copy link
Reaction Ethers, as this article explains, have a wide variety of applications as solvents in organic chemistry. This reaction demonstrates the initial step in the splitting of an ether by a hydrogen halide. copy link
Article section The first part of this section of the Organometallic compound article shows how titanium can be used for organic synthesis. The titanium complex shown as Structure 4 can be used to incorporate a stereocenter in a carbon skeleton. copy link
Article section This portion of a 2011 Research Review describes cross-coupling reactions. The chemists that developed these reactions jointly received the 2010 Nobel Prize for their influence on organic synthesis. The formation of carbon-carbon bonds through palladium-catalyzed cross-coupling of aryl halides and organometallic reagents has changed the landscape of synthetic organic chemistry and opened many possibilities for drug design and manufacture. copy link
Graph Through the use of spectroscopic tools, modern organic chemists can elucidate the molecular structure of an organic compound. This graph, from the article on nuclear magnetic resonance, shows a sample spectrum. copy link
News Modern spectroscopy also enlightens forensic efforts in organic structure determination. This news story, Chemists distinguish between gunshot residue from various firearms, highlights how spectroscopic structure determination allows scientists to find missing clues in solving real-life investigations. copy link
Carbonyl Chemistry
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Article Carbonyl, as this brief article explains, is the major functional group of aldehydes, ketones and other classes of compounds. copy link
Article section This section of the article on acetone—a highly useful organic solvent, and the simplest ketone—describes its production. copy link
Biography Georg Wittig pioneered work in preparing alkenes from carbonyl compounds. His synthetic method is still routinely used in the production of vitamin D3, for example. copy link
Article This article presents various kinds of tautomerism, the key mechanism for proton transfer in ketones and aldehydes that results in formation of a polyfunctinoal enol. The deprotonated enol becomes an enolate, which is an important part of a carbon-carbon bond-forming reaction. copy link
Diagram This figure from the Bioorganic chemistry article shows an example of a Michael addition—a key bioorganic process in protein folding. copy link
Table This table from the Carboxylic acid article lists selected saturated monocarboxylic acids, and tells where they can be found in natural sources. copy link
Biography Nobelist Wilhelm Ostwald, as this biography describes, identified the color changes associated with certain acid-base reactions of carboxylic acids. Chemists now use those reactions as acid-base indicators in titrations. copy link
Biological Organic Chemistry
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Biography Emil Fischer worked to identify the structure of glucose, among other biologically important compounds. His proof of glucose remains one of the most amazing feats of organic chemistry, as it is analogous to a computer scientist developing the code for the World Wide Web in 1940. This biography hints at why Fischer is considered to be the father of modern biochemistry. copy link
Diagram Cellulose has many advantageous fibrous characteristics that can be tuned, or changed, based on simple stereochemical changes to the alpha/beta structure of the carbohydrate linkages. This figure from the Cellulose nanocomposites article shows the positions of reactive sites (hydroxyl groups) on the cellulose backbone. copy link
Diagram This figure from the article on carbohydrates identifies and classifies monosaccharides according to their carbon-chain length. copy link
Article This brief article describes lanolin, an example of a naturally occuring lipid used in ointments and cremes for treating irritated skin. copy link
Diagram These examples of terpenes, from the article on essential oils, represent a class of compounds that are precursors to many naturally occurring lipids. copy link
Table This table, from the article Fat and oil, displays the constituent fatty acids in a number of commercial glycerides. The effect of chain length and degree of unsaturation on the chemical and physical properties of these fats and oils is evident. copy link
Diagram This diagram from the Nucleotide article differentiate the structures of purines, pyrimidines, and nucleotides. copy link
Reaction The Traube method, shown in this reaction from the Purine article, is perhaps the most useful method for synthesizing purine compounds. copy link
Diagram This diagram from the article on DNA shows how the two sets of base pairs have the same geometry, allowing DNA to maintain the same structure regardless of the specific sequence of base pairs. copy link
Animation This animation explains the structure of DNA and shows how this molecule replicates. It is interesting to envision how the simple drawing becomes complex when the rungs of the DNA ladder are thought of as complex heterocyclic aromatic compounds instead of simple sticks. copy link
Photograph Nobel-Prize winning work on green fluorescent protein has been highly useful in visualizing RNA at work, as this image from a 2013 Research Review shows. copy link
Animation This animation provides a quick, yet useful, summary of amino acids, peptides, and proteins. copy link
News Meteorites, such as the one featured in this news story, could have provided the material needed to form amino acids, the building blocks of life. copy link
Table This table from the Amino acids article classifies amino acids into nine categories based on molecular structure. copy link
Article section This section of the Proteins article describes several methods of protein analysis. copy link
Article This brief article defines peptides, and describes their synthesis. copy link
Video Biography Jerrold Meinwald received the Benjamin Franklin Medal in Chemistry for his advancement of chemical ecology. Chemical signaling like that present in a skunk's spray is critical for communication among predator and prey in natural ecosystems. Molecules that contain a sulfur atom can be highly useful as synthetic organic reagents as well as chemical signaling for interspecies communication. copy link