CTP 005614

Committee on Professional Training
Organic Chemistry Supplement

Context
Carbon-based molecules are central to a host of chemical and biological processes because of their
broad range of structure and reactivity. The millions of organic compounds alone, ranging from
polymers to pharmaceuticals, make the field important for study. Yet organic chemistry is also a highly
integrated discipline that impacts and is impacted by the other branches of chemistry and other
sciences. Indeed organic chemistry enables a molecular understanding of physicochemical
phenomena in material science, the environment, biology, and medicine. The field has reached a high
level of maturity, yet progress in organic chemistry continues at a fast pace and much more remains to
be discovered.
It is nearly impossible to master the breadth of organic chemistry in only an introductory course
sequence, but it is important that students understand the principles and learn to apply them to gain a
working knowledge and appreciation of organic structure and reactivity.
Conceptual Topics
• The understanding that our only way to molecular knowledge is through experimentation;
correlating structure with reactivity and function through wet chemical methods,
spectroscopy, (notably nuclear magnetic resonance and infrared spectroscopy and x-ray
crystallography) and use of computational methodology.
• Bonding and its consequences on molecular structure and reactivity.
• Interplay between electronic, steric, and orbital interactions in the behavior and properties of
molecules.
• The dependence of structure and reactivity on context, the environment, whether gaseous,
liquid or solid; or in solution.
• Lewis and Bronsted acid-base chemistry.
• Stereochemistry and conformational analysis.
• Addition, elimination, substitution and rearrangement mechanisms, and reactive

intermediates.
• Functional groups, with particular emphasis on the centrality of the carbonyl group in
organic reactions.
• Organic synthesis, including retrosynthetic analysis of target molecules.
• Synthesis and behavior of macromolecular species, including biomolecules such as

proteins and polysaccharides and synthetic polymers.
-1-
Practical Topics
The laboratory portion of the organic chemistry experience should demonstrate how organic chemical
knowledge is acquired through experimentation. Laboratory skills and techniques are important, as are
the skills of asking questions and answering them by the analysis of experimental data. Working in
teams can be useful in the latter.
• Developing a feel for the logic of organic experimental procedures: the logic of glassware
design, selecting the optimum equipment for a particular reaction or operation, why
particular solvents and reaction conditions are used for a specific transformation.
• Planning and carrying out a variety of organic reactions, including safety considerations.
• Keeping a laboratory notebook as a record of what is done.
• Monitoring the progress of a reaction.
• Isolation and purification of products.
• Spectroscopic analysis of starting materials and products; deducing structures and

answering questions from modern spectroscopic and computational data.
• Analysis of experimental data using statistical analysis.
• The value and limitations of computational methods.
Illustrative Modes of Coverage

The foundation experience in organic chemistry is generally presented as a two-semester (or
equivalent) sequence of courses and associated laboratories. While it is usually taught in the second
year, some institutions teach part of it with success in the first year. Where a one-semester foundation
course is used to support other course work such as biochemisty, the topics in that course must be
carefully chosen. Some topics appropriate for the foundation course that supports biochemistry include:
• carbonyl chemistry, including nucleophilic addition, alkylation and condensation reactions
• oxidation and reduction
• nucleophilic substitution reactions
• addition and elimination
• acidity and basicity of organic compounds
• stereochemistry, as applied to the previous topics
• concepts and consequences of resonance and aromaticity
• spectroscopy at a basic level as applied to the previous topics
Since this may be the only course in organic chemistry a student may see, the lecture and laboratory
must reinforce each other. It is appropriate for the primary treatment of spectroscopy, including NMR
and IR spectroscopy, to be done in the laboratory setting.
-2- Last revised in August 2008

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Committee on Professional Training

Organic Chemistry Supplement

• Bonding and its consequences on molecular structure and reactivity.

• Lewis and Bronsted acid-base chemistry.

• Stereochemistry and conformational analysis.

• Addition, elimination, substitution and rearrangement mechanisms, and reactive

• Organic synthesis, including retrosynthetic analysis of target molecules.

• Synthesis and behavior of macromolecular species, including biomolecules such as

• Keeping a laboratory notebook as a record of what is done.

• Monitoring the progress of a reaction.

• Isolation and purification of products.

• Spectroscopic analysis of starting materials and products; deducing structures and

• Analysis of experimental data using statistical analysis.

• The value and limitations of computational methods.

Illustrative Modes of Coverage

• carbonyl chemistry, including nucleophilic addition, alkylation and condensation reactions

• oxidation and reduction

• nucleophilic substitution reactions

• addition and elimination

• acidity and basicity of organic compounds

• stereochemistry, as applied to the previous topics

• concepts and consequences of resonance and aromaticity

• spectroscopy at a basic level as applied to the previous topics

-2- Last revised in August 2008

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