does the carbonyl group make it more polar or less polar?
2007-02-14 16:56:07 · 2 answers · asked by haleyzxx 2 in Science & Mathematics ➔ Chemistry
which would run higher on TLC with 50% ethyl acetate/hexane? i would assume aniline?
2007-02-15 15:24:51 · update #1
Be careful.
Aniline can be protonated at the -NH2 group and the protonated form is more polar and more soluble in water/polar solvents.
When it forms the peptide bond it cannot get protonated and thus it will be less polar.
If you compare the neutral form of aniline to acetanilide then the difference won't be much-although you are introducing a O which can participate in H-bonds (as an acceptor) you are losing one H from the amino-group, thus 1 possibility for hygrogen bonding.
2007-02-14 23:01:01 · answer #1 · answered by bellerophon 6 · 0⤊ 0⤋
The extra oxygen undoubtedly makes it more polar, so acetanilide wins!
2007-02-15 03:34:49 · answer #2 · answered by Gervald F 7 · 0⤊ 0⤋