hydrophobic solvent

[AntonFreeman]

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What is hydrophobic solvent? I ran into a passage in OCHEM book from TBR. How does it impact amino acids hydrophobic solvents?

 

[MT Headed]

What is hydrophobic solvent? I ran into a passage in OCHEM book from TBR. How does it impact amino acids hydrophobic solvents?

I imagine it is a solvent that hates water, i.e. some kind of nonpolar solvent like CCl4 or benzene that would dissolve hydrophobic solutes but be unable to penetrate the polar intermolecular bonds of hydrophilic solutes like water or amino acids.

 

[salim271]

I imagine it is a solvent that hates water, i.e. some kind of nonpolar solvent like CCl4 or benzene that would dissolve hydrophobic solutes but be unable to penetrate the polar intermolecular bonds of hydrophilic solutes like water or amino acids.

Pretty much, and if the amino acids are linked together into a tertiary/quaternary protein, they will have a different shape in a hydrophobic solvent in comparison to a hydrophilic due to hydrophobic interactions.

 

[oasis67]

In the TBR book, there is a question where an amino acid is completely uncharged because it is in a hydrophobic solvent. Do hydrophobic solvents deprotonate the amino terminal?

 

[loveoforganic]

Charges don't jive well with nonpolar solvents, so the relative energy of going to the zwitterion from the uncharged species goes up.

 

[MD Odyssey]

In the TBR book, there is a question where an amino acid is completely uncharged because it is in a hydrophobic solvent. Do hydrophobic solvents deprotonate the amino terminal?

Look at the common non-polar solvents you're going to run into in a lab: ether, hexane, toluene, et.al. None of those are really going to be able to bear a positive charge, so an acidic proton has nowhere else to go. Of course, it's possible that the -COOH might donate its proton to the -NH2 end of another amino acid, but that's very unfavorable energetically, so the amino acids are going to be largely neutral.