16 Jul 2012

Application of Organometallic Chemistry – Breaking the Inert C-H Bond

In-Class Activity

Submitted by John Lee, University of Tennessee Chattanooga

This learning object is a literature discussion based on a paper published in Nature (Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507-514; doi:10.1038/446391a) discussing the mechanisms of C-H activation by transition metal complexes. This is a topic that could be covered at the end of a section on organometallic chemistry that shows a “newer” application. The attached lecture notes start at organic chemistry, then asks a question and is followed by a brief description of the paper showing examples for different mechanisms. The last slide is a thought slide that can easily be removed that asks a question that builds both upon what was discussed in the lecture and previous organometallic lectures. A working knowledge of counting electrons is required before beginning this study.

Learning Goals: 

A student should be able to describe, in limited detail, the “five primary” mechanisms for C-H activation.

A student should be able to distinguish the basic characteristics between oxidative addition, sigma-bond metathesis and electrophilic substitution.

A student should be able to apply his/her knowledge of organometallic reactions to show these reactions in a catalytic cycle for C-H functionalization.

Equipment needs: 


Implementation Notes: 

A copy of the paper and guided questions should be made available to students one week prior to the lecture.  A 15 minute powerpoint lecture is available, if needed.  At the end of the lecture allow the students to break into small groups to take a second attempt at their guided questions. During this time the instructor can walk around helping with both the guided questions and any other questions that might have arisen from the discussion.  Alternatively, if the presentation is not needed you can use the guided questions to lead the class in a discussion.

Time Required: 
50 minute lecture
Evaluation Methods: 

The guided questions can be collected and graded. Alternatively, a qualitative score can be given based on class participation.

Creative Commons License: 
Creative Commons Licence

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