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-1 votes
1 answer
270 views

intramolecular h-bonding in maleic acid

While studying organic chemistry, I came across two practice questions given by my professor: Compare the acidic strength of:- Maleic acid and Fumaric acid o-nitrophenol and p-nitro phenol And the ...
Priyanshu Choubey's user avatar
12 votes
2 answers
2k views

Why hydrogen bonding in some acids make them a stronger acid when it is present even before deprotonation?

If we take the example of salicylic acid, hydrogen bonding is present in the acid as follows: Even after deprotonation, it has intramolecular hydrogen bonding as follows: My question: p-...
Neha's user avatar
  • 452
1 vote
1 answer
157 views

Why don't dicarboxylic acids show hydrogen bonding in spite of the fact that carboxylic acids exist usually as dimers in polar aprotic solvent? [closed]

I have seen several examples: The fact that maleic acid is more soluble in water than fumaric acid in spite of the fact that it must be able to show intramolecular hydrogen bonding. trans-...
Very Useless's user avatar
-1 votes
2 answers
154 views

If acid releases proton then how can a proton react with another proton to form hydrogen gas? [duplicate]

As we know that acid releases proton (H+ ion) when dipped in water hydrogen has a proton and electron only . To form H+ hydrogen releases 1 electron and it becomes proton. But when Acid reacts with ...
Roshan kumar's user avatar
3 votes
1 answer
2k views

Why HI isn't fully miscible with cold water when HF is?

HF is more soluble in water than HI, due to greater hydrogen bonding in HF, accepted, but on the other hand HF is a weak acid so it's dissociation will be meagre when compared to HI's dissociation, so ...
Aditya Prakash's user avatar
7 votes
0 answers
1k views

Steric inhibition of resonance vs. hydrogen bonding

I have to compare the acidic strength of these compounds: Now, in A and B hydrogen bonding will be present which will help stabilize the negative charge of the conjugate base. However, the hydroxyl ...
xasthor's user avatar
  • 1,632
5 votes
3 answers
5k views

Hydrogen bonding relating to molecular orbital theory

In [1, p. 232] here is an explanation of how alcohols hydrogen bond to each other and I do understand how the alcohols form hydrogen bonds to each other: FIGURE 6.15 Water and alcohols are both ...
Mousedorff's user avatar
7 votes
1 answer
6k views

Which dicarboxylic acid has the most acidic hydrogen?

Which of the following acids (maleic, fumaric, succinic, or malonic) has the most acidic hydrogen? I think that malonic acid should have the most acidic hydrogen due to the presence of an active ...
Prakhar's user avatar
  • 2,381
3 votes
1 answer
297 views

If hydrogen bonding in water was weaker, what happens to H+ ion concentration?

Water ionization becomes much less evident if the hydrogen bonds are just a few percent stronger but pure water contains considerably more $\ce{H+}$ ions if they are few percent weaker. I found this ...
dsinghvi's user avatar
  • 1,796
14 votes
2 answers
2k views

Does hydrogen bonding strength correspond to Brønsted basicity in a given medium?

It does seem that there is a correlation. Both are measures of proton affinity. Heck, isn't hydrogen bonding present in the transition states of most acid base reactions (excluding those involving ...
Dissenter's user avatar
  • 19k
15 votes
1 answer
12k views

Why does hydrogen bonding in salicylic acid make it more acidic?

When salicylic acid deprotonates (losing the proton from the carboxyl group) it forms a hydrogen bond with between the oxygen in the carboxylate anion and the hydrogen in the alcohol group. However, ...
RobChem's user avatar
  • 9,802