Reaction mechanisms

8 Jun 2019

VIPEr Fellows 2019 Workshop Favorites

Submitted by Barbara Reisner, James Madison University

During our first fellows workshop, the first cohort of VIPEr fellows pulled together learning objects that they've used and liked or want to try the next time they teach their inorganic courses.

5 Jun 2019

Zinc-Zinc Bonds (Expanded and Updated)

Submitted by Wesley S. Farrell, United States Naval Academy
Evaluation Methods: 

Performance and participation in the discussion will be assessed 

Evaluation Results: 

None collected yet. Evaluation data will be added in the future.


This paper in Science reports the synthesis of decamethyldizincocene, a stable compound of Zn(I) with a zinc-zinc bond. In the original LO, the title compound and the starting material, bis(pentamethylcyclopentadienyl)zinc, offer a nice link to metallocene chemistry, electron counting, and different modes of binding of cyclopentadienyl rings as well as more advanced discussions of MO diagrams. More fundamental discussion could focus on the question of what constitutes the evidence for a chemical bond, in this case, the existence of a zinc-zinc bond. In this updated LO, these topics are still covered, however additional topics, such as point group idenitifaction, details regarding the reaction mechanism, electronic structure, and  searching the literature using SciFinder are covered.  Additionally, electron counting is divided into both the covalent and ionic models.

Course Level: 
Learning Goals: 
  1. Students should become more confident reading the primary literature

  2. Students should be able to apply existing knowledge to interpret research results.

  3. Students should be able to apply electron counting formalisms to organometallic compounds.

  4. Students should be able to use 1H NMR spectroscopy data to rationalize structure.

  5. Students can rationalize bond distances based on periodic trends in atomic radii

  6. Students use SciFinder to put this work into a larger context.

  7. Students identify redox reactions based on oxidation changes.

  8. Students identify molecular point groups based upon structures.

  9. Students should be able to connect d electron count to observed colors of compounds. 

Related activities: 
Implementation Notes: 

Students are asked to read the paper and the accompanying Perspectives article before class as well as answer the discussion questions. The questions serve as a useful starting point for class discussion. 

Time Required: 
50 minutes
7 Apr 2019

Encapsulation of Small Molecule Guests by a Self-Assembling Superstructure

Submitted by Shirley Lin, United States Naval Academy
Evaluation Methods: 

I have not yet implemented this LO. As with other literature discussions, instructors could collect the completed worksheets (by an individual student or in groups of students) for evaluation.

Evaluation Results: 

I have not yet implemented this LO so there are currently no evaluation results to share.


This literature discussion focuses upon two journal articles by the Rebek group on the synthesis and host-guest chemistry observed with the "tennis ball." 

Learning Goals: 

After completing this literature discussion, students will be able to:

  • provide examples of supramolecular systems in nature that use reversible, weak noncovalent interactions 
  • define terms in supramolecular chemistry such as host, guest, and self-complementary
  • identify the number and location of hydrogen bonds within the "tennis ball" assembly
  • draw common organic reaction mechanisms for the synthesis of the "tennis ball" subunits
  • describe the physical and spectroscopic/spectrometric techniques used to provide evidence for assembly of a host-guest system
  • explain the observed thermodynamic parameters that are important for encapsulation of small molecule guests by the "tennis ball"
Implementation Notes: 

This LO could be used at the end of a traditional 2-semester organic chemistry sequence as an introduction to organic supramolecular systems, as an organic chemistry example within a discussion about inorganic supramolecular chemistry, or in an upper-division elective course about supramolecular chemistry. The LO topic, the "tennis ball," has a published laboratory experiment in J. Chem. Educ. (found here). Time permitting, instructors could have students read the article and complete the literature discussion before executing the experiment in the lab.

As usual, instructors may wish to mix-and-match questions to suit their learning goals.

Time Required: 
depends upon implementation; minimum of 20-30 minutes for the literature discussion if students read an d answer questions outside of class


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