Organic Chemistry

10 Jun 2020

A copper "Click" catalyst for the synthesis of 1,2,3-triazoles

Submitted by Chip Nataro, Lafayette College
Evaluation Methods: 

I have not used this in class yet, but anticipate updating this after the fall 2020 semester. This comes as a result of the June 9th LO party.

Description: 

This paper (Gayen, F.R.; Ali, A.A.; Bora, D.; Roy, S.; Saha, S.; Saikia, L.; Goswamee, R.L. and Saha, B. Dalton Trans2020, 49, 6578) describes the synthesis, characterization and catalytic activity of a copper complex with a ferrocene-containing Schiff base ligand. The article is relatively short but packed with information. However, many of the details that are assumed knowledge in the article make for wonderful questions some of which I hope I have captured. The LO includes electron counting using the CBC method, d-orbital splitting, Latimer diagrams and interpretation of catalytic results. There are also opportunities to discuss green chemical practices.

Corequisites: 
Prerequisites: 
Course Level: 
Learning Goals: 

A student should be able

determine the electro count and metal valence in the catalyst

use group theory to determine the number of IR active vibrations in the catalyst

discuss green chemical principles in relation to this article

interpret data from tables and draw conclusions from that data

suggest an additional catalytic experiment that could be performed

Implementation Notes: 

I like the question invoking a Latimer Diagram to get students to rationalize why the copper(I) active catalyst was not isolated. I also enjoyed sneaking in a group theory question. But my favorite quesiton is the last one in which students are asked to go beyond what it presented in the paper and suggest another catalytic reaction to perform. There are some aspects of the paper that were not covered in-depth. In particular the XPS seemed to be a rabbit hole I opted not to go down. The authors do not go into great detail on this topic and perhaps there is a question that could be included, but I opted not to. I also opted not to include anything about the bonding in ferrocene which can be found in many of my other LOs. Also on this list one might include UV-Vis spectroscopy and the computational studies.

Time Required: 
50 minutes
21 Mar 2020

chromium and molybdenum arene complexes (COVID-19 version)

Submitted by Adam R. Johnson, Harvey Mudd College
Evaluation Methods: 

i have no idea.... yet! (growth mindset!)

Evaluation Results: 

I will report this later this spring.

Description: 

The synthesis of (arene)Cr(CO)3 and (arene)Mo(CO)3 complexes are fairly standard experiments in the organometallic curriculum. I present here some student data and experimental descriptions of real procedures carried out at Harvey Mudd College over the previous two to three years. The word document has the answers in it so it is posted under "faculty resources" but the raw data (pdf or png form) is presented for those who need data to support their distance learning classrooms in the Spring of 2020. I also include an input file for Mo(benzene)(CO)3 should you desire to use WebMO or Gaussian to carry out some calculations. 

 

there was a minor mistake in the reported integrations for one of the complexes in the original faculty only file; it has been fixed in the v2 version.

Course Level: 
Prerequisites: 
Corequisites: 
Learning Goals: 

Students will interpret provided data to write their own experimental sections for molecules they were unable to prepare in the lab. The guided inquiry part allows students to use data to predict the outcome of a chemical reaction.

Equipment needs: 

be able to view PDF/PNG files

Implementation Notes: 

I have not used this yet but will be using it spring 2020.

Time Required: 
unknown
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.

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.

Description: 

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

Corequisites: 
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
3 Apr 2017
Description: 

A novel family of nonadentate ligands based on the (5,6-diphenyl-1,2,4-triazin-3-yl)-picolinamide donor moiety has been synthesized from simple starting materials in high yield and purity. This group of ligands is an addition to the neutral nonadentate group but the first to incorporate 1,2,4-triazine. Their ability to extract a select group of lanthanides from acidic aqueous solution has been correlated to their ability to meet the ideal trigonal tricapped prismatic geometry that is seen by lanthanides and actinides in aqueous solution. The rate of metallation was determined using UV/VIS spectroscopy with pseudo first order conditions and showed similar behaviour to literature examples. Theoretical calculations were used to probe the bonding structure with lanthanides and actinides to predict the potential Ln/An segregating ability of the new ligands.

 

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4 Jan 2017
Description: 

This is a great new textbook by George Luther III from the University of Delaware.  The textbook represents the results of a course he has taught for graduate students in chemical oceanography, geochemistry and related disciplines.  It is clear that the point of the book is to provide students with the core material from inorganic chemistry that they will  need to explain inorganic processes in the environment.  However the material is presented in such a clear, logical fashion and builds so directly on fundamental principles of physical inorganic chemistry that the book is actually applicable to a much broader audience.  It provides a very welcome presentation of frontier orbital theory as a guide to predicting and explaining much inorganic chemical reactivity.  There are numerous very  helpful charts and tables and diagrams.  I found myself using the book for a table of effective nuclear charges when I was teaching general chemistry last semester.  The examples are much more interesting that the typical textbook examples and would be easy to embellish and structure a course around.  There is also a helpful companion website that provides powerpoint slides, student exercises and answers.  The book covers some topics not typically seen in inorganic textbooks like the acidity of solids but the presentation of this information makes sense in light of the coherent framework of the text.  We so often tell our students "structure dictates function".  This text really make good on that promise.  My only complaint is that I wish the title were something more generic so that I could use it for a second semester of introductory-esque material that we teach after students have taken a single semester of intro chem and two semesters of organic chemistry.  So much of what is covered in this textbook is precisely what a second semester sophomore chemistry major should know before proceeding on in the major.  But the title makes the book hard to sell to chemistry majors and that is regrettable. 

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29 Jul 2016

Chapter 7--Stanley Organometallics

Submitted by George G. Stanley, Louisiana State University
Description: 

Chapter 7 from George Stanley's organometallics course, Alkenes and Alkynes

 

this chapter covers bonding and structure of metal pi-bonds, some descriptive chemistry, and their NMR spectroscopy.

The powerpoint slides contain answers to some of the in-class exercises, so those are behind the "faculty only" wall. I shares these with students after the class, but not before.

everyone is more than welcome to edit the materials to suit their own uses, and I would appreciate being notified of any mistakes that are found.


 

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Course Level: 
29 Jul 2016

Chapter 6--Stanley Organometallics

Submitted by George G. Stanley, Louisiana State University
Description: 

Chapter 6 from George Stanley's organometallics course, Alkyls

 

this chapter covers bonding and structure of metal alkyls, some descriptive chemistry, and their NMR spectroscopy.

The powerpoint slides contain answers to some of the in-class exercises, so those are behind the "faculty only" wall. I shares these with students after the class, but not before.

everyone is more than welcome to edit the materials to suit their own uses, and I would appreciate being notified of any mistakes that are found.


 

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