Why is parahydroxybenzaldehyde more soluble in water than orthohydroxybenzaldehyde?

Question

Why is parahydroxybenzaldehyde more soluble in water than orthohydroxybenzaldehyde?

Hey Gervald.
Thanks for your answer.. i have another doubt.. is this a good answer to my question:
Parahydroxybenzaldehyde is a non-polar molecule and orthohydroxybenzaldehyde is a polar molecule.. and hence the former is more soluble in water than the latter?

Answer 1

The ortho compound has internal hydrogen bonding, but the para compound hydrogen bonds extrremely well to external molecules such as water.

Answer 2

"Parahydroxybenzaldehyde is a non-polar molecule and orthohydroxybenzaldehyde is a polar molecule.. and hence the former is more soluble in water than the latter?"

Well I was thinking along those lines, but in actuality a polar molecule would be more soluble in water. So unless para- is actually polar and ortho- is nonpolar, looking at polarity of the molecules is not a valid answer.

Answer 3

Lancenigo di Villorba (TV), Italy

I CONFIRM GERVALDF's OPINION....MEANWHILE,
HE LET SOME CONFUSION....YOU NEWLY ASKED :"WHY A NON-POLAR COMPOUND SHOW A GREATER 'WATER-SOLUBILITY' THAN A POLAR ONE?".
Polarity needs not in all the cases.

I start sketching a draw of HYDROXY-BENZALDEHYDE's Isomers

...........H
............|
...........C
.........//...\
....H-C....C-O-H
.........|......||
....H-C....C-C-H
.........\\..../....||
...........C.....O
............|
...........H.....o-HYDROXY-BENZALDEHYDE
...................(e.g. it is POLAR)

...........O-H
............|
...........C
.........//...\
....H-C....C-H
.........|......||
....H-C....C-H
.........\\..../
...........C
............|
......O=C-H.....p-HYDROXY-BENZALDEHYDE
.......................(e.g. it is NON-POLAR)

WHAT are the ATOMs INVOLVED in the SECUNDARY CHEMICAL BONDs? I highlight the role played by Oxygen Atom in CARBONYLIC GROUP and by Hydrogen Atom in the OXYDRILIC GROUP : THESE TWO ATOMs INTERACT BY THE STRONGEST AMONG THE PERMITTED SECUNDARY BONDs.
IN THE FORMER CASE, o-HYDROXYBENZALDEHYDE acts its SECUNDARY BOND MAINLY IN INTRAMOLECULAR PLACE while
p-HYDROXYBENZALDEHYDE acts its SECUNDARY BOND MAINLY IN INTERMOLECULAR PLACE.
Hence, p-isomer may interacts the one molecule with the other ones by means of intermolecular bonds belonging to "HYDROGEN BOND's TYPES" ; o-isomer cannot do it, its intermolecular bonds belonging to "VAN DER WAALS's TYPE", it is very weaker than the Hydrogen Bond's One.

I hope this helps you.

Answer 4

idk..//?