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From
Using Trityl Carbocations to Introduce Mechanistic Thinking to German High School Students
Catharina Schmitt, Michael Schween
World Journal of Chemical Education
.
2018
, 6(1), 18-23 doi:10.12691/wjce-6-1-4
Figure
1.
General chemistry takes a more product-oriented view (left), whereas organic chemistry engages in process-oriented thinking (right). The workshop “carbocation watching” focusing on mechanistic pathways is designed to help students make this shift in chemical thinking
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Scheme
1
.
Reaction of chlorotriphenylmethane with aluminum(III) chloride
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Figure
2.
Four out of the ten possible resonance forms for the trityl cation
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Scheme
2.
Reaction of chlorodiphenylmethane with aluminum(III) chloride
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Figure
3.
Comparative energy diagram showing the formation of the trityl cation (blue) and the benzhydryl cation (black)
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Scheme
3.
Reaction of 4,4',4''trimethoxychlorotriphenylmethane with aluminum(III) chloride
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Figure
4.
Learning chemical basic concepts by conducting the six-step workshop, interlocking theoretical and practical phases
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Figure
5.
Reaction of chlorotriphenylmethane with aluminum(III) chloride and potassium hydroxide in dichloromethane. a) shows the solution of chlorotriphenylmethane in dichloromethane, b) the solution 2 min after the addition of aluminum(III)chloride and c) the solution after the addition of 3 mL potassium hydroxide in ethanol
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Figure
6.
Reaction of chlorodiphenylmethane with aluminum(III) chloride and potassium hydroxide in dichloromethane. a) shows the solution of chlorodiphenylmethane in dichloromethane, b) the solution 2 min after the addition of aluminum(III)chloride and c) the solution after the addition of 3 mL potassium hydroxide in ethanol.
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Figure
7.
Dissociation of 4,4′,4′′-trimethoxychlorotriphenylmethane in dichloromethane. a) shows the solid reactant and b) the reactant dissolved in dichloromethane after 2 min
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Figure
8.
The reaction progress of the formation of trityl cation. Listed are the most important concepts covered in the experiments, focusing on the process-oriented approach
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