A Teacher’s How-to Guide for Unlocking the Mysteries of Organic Chemistry

Organic Chemistry in the High School Classroom – with ChemDraw® 

Several hundred thousand high school students take an advanced chemistry elective every year.  Most of these students follow a traditional American curriculum centered on topics covered in a standard introductory college course, with units like electron structure and periodicity, bonding, thermodynamics, kinetics, acids and bases, and the like.  The Advanced Placement Chemistry program codifies this curriculum into a standard form that is followed by thousands of chemistry teachers.  But there is another interesting option for a second year high school chemistry elective: organic chemistry!  And tools like ChemDraw® make it easy to build exciting and powerful lessons focused around OChem.  

The high school organic course we have taught at Lakeside School for the past 16 years is a hybrid between a traditional college OChem course covering the intricacies of organic structures and reactions, and a more topical course that explores the world of polymers and other macromolecules, petroleum and biofuels, soaps and surfactants, dyes and pigments, and food chemistry.  I use ChemDraw extensively in nearly every unit, from making images for my lectures and homework packets to creating activities and labs for my students to work on during class.  Here are some examples of how I use the amazing tools that ChemDraw offers to help my students unlock the mysteries of organic chemistry.

Molecular Structure

I start the year exploring the many levels of molecular structure inherent in organic molecules with a series of molecular modeling labs.  We start by looking at the variation present in constitutional isomers.  Students build different branched alkanes, name them, and find their corresponding constitutional isomers

the constitutional isomers of heptane, C7H16

From there we move to looking at how conformatial changes can affect molecular structure, starting with the conformers of butane and working up to the conformational equilibria present in substituted cyclohexanes.

gauche butane                                                                                                     Conformers of cis-1,3-dimethylcyclohexane

Stereochemistry is a rich area to explore with high school students.  We spend some time looking at simple enantiomers, and then move into more complex aspects of stereochemistry like diastereomers and meso compounds

The enantiomers of 1-bromo-1-fluoroethane

I make extensive use of the amazing “Name to Structure” function in ChemDraw to look up real chiral molecules that the students might have heard of so that we can study their 3-D structure together.

Dexmethylphenidate, one the pharmacologically active configurational isomers found in the drug, Ritalin

While the “Name to Structure” feature is a real time-saver, the one I use even more frequently is “Structure to Name,” which allows to me instantly answer those persistent student questions of the type, “But how would you name THIS?”

“Easy, kid: it’s 1-((3S,5R,7R)-5-amino-3-chloro-7-methyloctahydrocyclopenta[c]pyran-4-yl)ethan-1-one, of course”

This function is even sophisticated enough to handle obscure structural features like prochiral centers.

A bromochlorocarbon with a prochiral center in the 3-position

Organic Reactions, Labs, and Spectroscopy

In addition to looking at levels of molecular structure, ChemDraw is very helpful in making up lessons and activities around organic reactions, labs, and NMR spectroscopy.  We spend quite a bit of time learning some basic organic reactions, and it’s easy to sketch out practice exercises and make up quizzes and tests:

Practice with some organic redox reactions

The clip art library makes illustrating lab handouts easy.  We usually do a fun and engaging steam distillation of lavender oil as our first real “wet lab” of the year.

ground glass labware used in our steam distillation

My students usually end the year learning spectroscopy, and ChemDraw has some cool features that I use in teaching students about Nuclear Magnetic Resonance.  For any given structure, ChemDraw can predict 1H and 13C NMR spectra, assign peaks, and calculate coupling constants.  

An estimated H-NMR spectrum for 3-methylbutan-2-ol

After learning the basics of spectra reading, I make up a bunch of “unknown” spectra for the students to analyze and have them try to predict the corresponding structures.  For many students, studying spectroscopy is one of most engaging topics we look at all year.

From isomers to spectroscopy, ChemDraw makes my high school organic class possible.  I’d love to hear from other science teachers who are also teaching organic chemistry to high school students, and learn how you use ChemDraw and other tools to create interesting and meaningful lessons for your students.

About the author
Hans de Grys teaches organic chemistry to students at Lakeside School in Seattle, WA, where he is also the Assistant Director of e Upper School.  His favorite things to do with his students are making cold-processed soap in the lab, studying spectroscopy (especially NMR), and synthesizing banana oil and biodiesel.  You can follow him on Twitter @chiral_guy

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