WHICH ONE MORE ACIDIC

9 Answers

1
JOHNCENA IS BACK ·

well for a couple of reasons i go for a

29
govind ·

The second one is more acidic..coz in the first compound there will be intramolecular hydrogen bonding...

1
JOHNCENA IS BACK ·

yes absolutely right[1]

1
Tapas Gandhi ·

@govind-cant there be intErmolecular H-bonding in (B)

3
rocky ·

that's why i posted here.........
in the first compound there will be intramolecular hydrogen bonding.

but still order is given a>b [7]

4
UTTARA ·

Answer will be A

REASON :

Here we won't consider intramolecular H bonding in case B because - I effect is more

dominating over ortho effect {FACT}

If it were NO2 instead of F then ans wud be B

1
Tapas Gandhi ·

http://chemicalland21.com/lifescience/phar/o-FLUOROPHENOL.htm

http://chemicalland21.com/lifescience/phar/p-FLUOROPHENOL.htm

The inductive effect is more important here than the resonance effects because resonance structures where the fluorine has a + charge are very small contributors.

pKa of phenol = 10.0
pKa of ortho-fluorophenol = 8.81
pKa of meta-fluorophenol = 9.28
pKa of para-fluorophenol = 9.81


@govind- an analogy from above is NOT applicable, as F is more En than O

29
govind ·

ok...i didnt knew that

@Uttara and Tapas....thanks for the info... : )

1
Amar poonia ·

It is due to the -R effect of F.
As F is closer to OH in A therefore I'll gofor it!!!!

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