- #1
maverick280857
- 1,789
- 5
Hello again
My question:
Rank the following compounds in order of decreasing acidity:
(a) phenol
(b) o-nitrophenol
(c) m-nitrophenol
(d) p-nitrophenol
I know that (d) will be most acidic. But here's the problem: in orthonitrophenol the hydrogen of the -OH group satisfies the conditions for intramolecular hydrogen bonding and should in theory be bound to the nitrogen of the nitro substituent making difficult its loss as H+. So (c) should be more acidic than (b).
1. Is this reasoning correct?
2. Is o-nitrophenol more acidic than phenol despite the above reasoning (if at all the above reasoning is correct)?
3. What is the actual order of acidity.
I would be grateful if someone could help me out with this because I have two contradicting answers.
Thanks and cheers
Vivek
My question:
Rank the following compounds in order of decreasing acidity:
(a) phenol
(b) o-nitrophenol
(c) m-nitrophenol
(d) p-nitrophenol
I know that (d) will be most acidic. But here's the problem: in orthonitrophenol the hydrogen of the -OH group satisfies the conditions for intramolecular hydrogen bonding and should in theory be bound to the nitrogen of the nitro substituent making difficult its loss as H+. So (c) should be more acidic than (b).
1. Is this reasoning correct?
2. Is o-nitrophenol more acidic than phenol despite the above reasoning (if at all the above reasoning is correct)?
3. What is the actual order of acidity.
I would be grateful if someone could help me out with this because I have two contradicting answers.
Thanks and cheers
Vivek