[vande060]

For class I have to comment on the effects of adding alanine to a reaction occurring in water, just regular old ph 7 water.

the reaction is a diels alder reaction between anthracene-9methanol and n-methymaleimide:

http://greenchem.uoregon.edu/PDFs/GEMsID84.pdf

For our class we pitched in some amino acids, and my amino acid was alanine(.2g). My yield was actually about the same as what the reaction gives without alanine, but i feel this most likely was due to an error in my reflux.

I actually think that i should have had higher yields because i think the alanine should make the water more polar, and the reaction would go along better because the more polar water will push hydrophobic reactants together in the center of the flask. At ph 7 alanine has coo- on one end and NH3+, and once this happens all the water molecules immediately around alanine will have distortions in their electron density as a result of these charges, these distortions might have somewhat of a ripple effect causing transient dipoles throughout portions of the solution. I thought of this by remembering that water molecules solvating an ion will have a more polar character due to electron cloud distortions.

what do you think, is this sounding like a homework answer? is there any critical errors here? do think me prof will just look at me like i am a moron?(she already has a few times lol, but Einstein said A person who never made a mistake never tried anything new  )

[MissPhosgene]

How can the amino acid directly influence the reaction?

[vande060]

How can the amino acid directly influence the reaction?

I wasnt sure if it could because the reactants are so hydrophobic, and the alanine is very polar, wouldnt they just push away from each other. I was thinking more of how alanine makes the water solvent more polar to drive the reactants(diene and dieneophile) together in the middle of the solution so that they can react with each other