Submitted by Shirley Lin / United States Naval Academy on Sun, 06/26/2016 - 15:22
My Notes
Course Level
Topics Covered

This worksheet was designed to give students an introduction to organic chemistry nomenclature with a more active experience than listening to a faculty member present all the rules for how to name alkanes and cycloalkanes. The pedagogical approach is one introduced to me by Dr. Melonie Teichert; we refer to it as ICC (Inventing through Contrasting Cases). The theoretical framework involves the premise that students will learn and retain more of the learning if they're not simply told the "answer" but if they attempt to generate an answer for themselves based upon a data set.

Schwartz, D. L., Chase, C. C., Oppezzo, M. A., & Chin, D. B. (2011). Practicing versus inventing with contrasting cases: The effects of telling first on learning and transfer.  Journal of Educational Psychology, 103(4), 759-775.

In this case, the data set consists of the skeletal structures and names of the cycloalkanes (through 8 carbons), alkanes, and alkyls (through 12 carbons). From this data set, the students are asked a series of questions to draw their attention to the system used to name the compounds. At the end of the worksheet, they are asked to create a procedure for naming simple (non-branching) cycloalkanes, alkanes, and alkyls and then apply that procedure to a new example (transfer).


Learning Goals

After completing this worksheet, students will be able to...

1) Generate systematic names for non-branching cycloalkanes, alkanes, and alkyl substituents up to 12 carbons.

2) Explain the meaning of the prefix, root, and suffix of the name for a cycloalkane, alkane, and alkyl substituents.


Equipment needs

An answer key is provided (vide infra). The copy of the worksheet for the students deliberately does not include the structures for the tables. The instructor is encouraged to draw these on the board or on a blank copy of the worksheet so that the students can draw them into their own copies of the worksheet. This is beneficial as practice for this important skill. 


Students need pencils and the blank worksheet. 

Implementation Notes

I've used this worksheet the past two years that I've taught organic chemistry. Usually it is effective to organize the students into small groups (3-4), let them work on the sections of the worksheet for 5-10 minutes, and then bring the entire class together again to discuss the answers. I have also tried giving the students this worksheet and having them do it outside of class. In that case, it is difficult to know if the students really did it in the way that it was intended or if they just looked in the textbook for the answers.

If the instructor wishes, molecular model kits can be used to give a 3-dimensional experience with the molecules.

The worksheet introduces cycloalkanes before alkanes. The majority of organic chemistry textbooks discuss alkanes before cycloalkanes. The order in the worksheet was used so that students could relate the names of cycloalkanes to the names of the corresponding polygons in order to establish the correlation between the parts of the names (pent-, hex-, etc.).

Time Required
20 minutes


Evaluation Methods

This worksheet is intended to introduce and teach students the rules of organic compound nomenclature. I evaluate their performance on quiz and exam questions that give them the name and ask them to generate the structure or give them the structure and ask them to generate the name.

I'm interested in using common questions on exams that all the sections of organic chemistry take and see if the students who used this worksheet do better than the students who did not. If I do, I'll report back later.


Evaluation Results

None yet.

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