StudentGenerated Animated Reaction Mechanism Project Brandeis University Fall

Student-Generated Animated Reaction Mechanism Project Brandeis University Fall 2010 Reaction Type: Alkyne Allen, A. D. ; Chiang, Y. ; Kresge, A. J. ; Tidwell, T. T. J. Org. Chem. 1982, 47 (5), 775– 779. Organic Chemistry 25 Computer Science TYP

Project Goals • Improve chemistry understanding through student animation creation • Collaboration between student groups with different areas of expertise. • Generate a resource for other students to learn chemistry.

Animated Mechanism Goes Here! • CUE ANIMATION – We need to show… how the reaction happens – How it is relevant – Something really FREAKIN’ COOL!

One • • • Introduction: brief overview of molecule (where it comes from, etc. ) Electrophilic attack Animation: – – H 3 O (a certain color) unfolds into an Oxygen bonded to three hydrogens The arrow (a color) reaches out the hydrogen while the electrons binding the hydrogen to the oxygen move over to the oxygen arrow pulls in the hydrogen Computer people: Can we show this reaction forming slowly/slow motion? ? ?

Two • • • Nucleophilic attack Adding to carbocation Animation: – The H 2 O ( a color) unfolds into an oxygen bonded to two hydrogens – The arrow reaches out to the carbocation ( a color) from the H 2 O (same color) • show the arrow ( a color) pulling the H 2 O (still a color) along and forming a bond (a color, dashed line, or a flashing line)

Three • • Nucleophilic attack of water on Hydrogen Transfer of electrons from the OH bond onto the Oxygen Nucleophilic attack from alkene to the Hydrogen Animation: – H 2 O swoops in – Zoom into the top area where H 2 O and H are • arrow reaches out from H 2 O, pulls hydrogen towards itself or depict the electron density going into the s orbital of hydrogen as the electron density leaves it and goes onto the oxygen. – Move the picture downward • The OH bonds morph into (become) two sets of electrons and add onto the oxygen – Move the frame to the left • The alkene bond grabs onto the Hydrogen – Switch to next reaction step • • Transfer of electrons from the Oxygen to the CO bond forming a double bond Animation: – – The boring slide! How can we make this one awesome? electrons from the oxygen deform into (morph into) double bond

Credits The Orgo People: Rhianna Hibler Jason Karelis Minna Schmidt Shakara Scott The Computer People: Cameron Mendes-Moreau Terrell Gilkey The SSG Leader: Maralee Kanin The instructors: Dr. Jason K. Pontrello and Dr. Timothy J. Hickey