Solubility

[NA19]

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Why is C correct?

 

[Tamoores]

Why is C correct?

because its a carbocation and hence very reactive also its a good electrophile. the other structures are more stable than C due to resonance configuration.

 

[anegron519]

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[doctorswole]

There's an easier way to figure it out. Just remember FON. Fluoride, oxygen, nitrogen. Any one of these 3 elements paired with a hydrogen makes a hydrogen bond. We know that hydrogen bonds are stronger dipole dipole bonds and that they are polar. H2O also has hydrogen bonding and like dissolves like, so they are soluble.

A also has hydrogen bonding though

I'm going to say that C is better than A because of smaller size

 

[QrtrLifeCrisis]

A also has hydrogen bonding though

I'm going to say that C is better than A because of smaller size

👍

Those phenyl groups are mighty fat and heavy.

 

[anegron519]

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[QrtrLifeCrisis]

I thought it had 3 Ph's so I didn't see it write. I think tamoores is right. The positive on the nitrogen makes it carbocation. I haven't studied carbocation yet but just searching it up on google lol.

Not to be d*ck (I promise), carbocations are C+. That nitrogen is just a protonated cation, a weak acid.

 

[anegron519]

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[QrtrLifeCrisis]

Not to be d*ck (I promise), carbocations are C+. That nitrogen is just a protonated cation, a weak acid.

No it's cool. I didn't study carbocations yet and saw online they were C+ but assumed it could also be N+ since it was stated before. No harm done 🙂

Carbocations are fun! You'll love them. They show up EVERYWHERE in orgo 2 mechanisms.

 

[doctorswole]

I thought it had 3 Ph's so I didn't see it write. I think tamoores is right. The positive on the nitrogen makes it carbocation. I haven't studied carbocation yet but just searching it up on google lol.

carbocation = carbon cation

so nitrogen is just a cation

I am thinking that because nitrogen is a cation, it takes even more electron density from hydrogen, making hydrogen bonding between the hydrogen and the oxygen of water even stronger

but then you do not have the lone pair on nitrogen meaning you have less partial negative charge at nitrogen which might make hydrogen bonds to the nitrogen atom less strong

I don't know if these two things cancel out or make the molecule more or less soluble, but this is an interesting question

 

[anegron519]

Deleted

 

[QrtrLifeCrisis]

carbocation = carbon cation

so nitrogen is just a cation

I am thinking that because nitrogen is a cation, it takes even more electron density from hydrogen, making hydrogen bonding between the hydrogen and the oxygen of water even stronger

but then you do not have the lone pair on nitrogen meaning you have less partial negative charge at nitrogen which might make hydrogen bonds to the nitrogen atom less strong

I don't know if these two things cancel out or make the molecule more or less soluble, but this is an interesting question

Right, which is why I struggled to figure out why C is the answer over A. But I think your original thought on those big Ph groups making A less soluble might be the right way justifying that C is the answer.

 

[doctorswole]

Right, which is why I struggled to figure out why C is the answer over A. But I think your original thought on those big Ph groups making A less soluble might be the right way justifying that C is the answer.

yeah I was thinking that it might be due to steric hindrance

it is funny how such a short question can result in so much uncertainty

 

[anegron519]

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