The Organic Fold-a-Matic™

Introduction

Just about every organic compound you’ll ever need to know, from octane to propyne to hexanoic acid to fluoropentanol to hexylmethyl ether... are all represented in this fun and challenging folding card... over 1,300 compounds in all!

The Organic Fold-a-Matic™ is a fun and easy way to learn organic nomenclature: just follow the instructions on the next pages to learn how carbon chains and functional groups are pieced together to form a huge variety of organic compounds and how specific prefixes and suffixes fit together to form their appropriate names.

Naming organic compounds can be confusing because of the wide variety of possible organic compounds, multiple structural possibilities, the use of many Latin or Greek roots, and the widespread use of common or trivial names given to organic compounds when they were first discovered in the 1800s. In the late 1800s, a systematic approach to naming organic compounds was developed that used interrelated names that reflect structural relationships among compounds. The first set of rules was developed in 1892 by a group now known as the International Union of Pure and Applied Chemists which is still responsible for updating the rules.

For many simple organic compounds, the name consists of a function name (which has several parts) and prefixes which identify additional functional groups. The functional name can contain up to three parts:

• The root, which indicates the number of carbon atoms in the longest hydrocarbon chain of the molecules [e.g., but (4), pent (5), hex (6), hept (7)].
• An ending or suffix, which shows the functional group and/or the degree of unsaturation. The degree of unsaturation fragment comes directly after the root name and is either -an- for no carbon–carbon multibonds, -en- for a carbon–carbon double bond or -yn- for a triple bond. The functional group name is the last fragment of the compound name.
• A prefix, which indicates an additional hydrocarbon chain (e.g., methyl), functional group (e.g., halogen) or structural arrangement (e.g., cyclo or iso).

The Organic Fold-a-Matic is an easy tool to learn how these various parts of the organic compound fit together into a descriptive name. By folding the tool, both the structure and its name are formed!

Prelab Preparation

Caution: Please read through all the directions before starting.

1. Carefully cut along all solid lines (see Figure 1). Do not cut along dashed lines!
   {12254_Preparation_Figure_1}
2. Now fold crisply along all dashed lines. Note the diagram at the bottom of the page: the folded flaps are labeled “1-a” through “10-e” for easy reference. Important: Due to printing inconsistencies, the dashed lines may be slightly off. Use them only as approximate folding lines. The precise folds should be made to make the bonds line up (see Figure 2). For example, when you fold down flap 4 to change propane into pentane, make sure the bonds (circled in the diagram at right) line up before fully creasing the flap.
   {12254_Preparation_Figure_2}
   Also, sideways folds should be made to allow the small matching arrows to align (see Figure 3). Now you are set to produce just about any organic compound you please.
   {12254_Preparation_Figure_3}

Procedure

Much of the fun and challenge of the Organic Fold-a-Matic comes from exploring on your own the different combinations and folding sequences, the molecular structures they produce and the names that correspond with them (see Figure 4).

If you wish, skip the following instructions and just start folding! If you would like a little more direction, however, follow the directions in Figure 5. Example 1: Start with the propane facing you, then fold flaps over onto propane to change it into other compounds.

• Fold over flap 1-a to make octane.
• Fold over flap 1-b to make decane.
• Fold over flap 1-c to make heptane.
• Finally, fold over flap 3-a to make bromoheptane!

Example 2: Start again with propane, fold over flap 5 to make butane, then flap 7 to make butene.

Example 3: Start again with propane, fold over flap 8-a to make 1-propanol, then flap 8-b to make propanoic acid, then 9-b to make propanal, then 9-c to make propanamide.

Get the idea? Enjoy!
Note: A few additional compounds are represented on the back side: namely methane and ethane, and some of their derivatives. These are all pretty much self-explanatory, and the ethane variations help to illustrate the numbering system for substituted alkanes.

Student Worksheet PDF

12254_Student1.pdf

12254_Teacher1.pdf

References

Special thanks to Robert Becker, Kirkwood High School, St. Louis, MO, and John Roeder, The Calhoun School, New York, NY, co-developers of the Organic Fold-a-Matic.