Destroyer number 218 - Organic question- Which compund is most soluble in water?

[Mrhyde]

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Dat Destroyer number 218 organic chemistry.....


I believe the most soluble will be R-OH , alcohol

But the book said it was R-COOH, Carboxylic Acid as the correct answer .....

I have a confusion now with the book saying that R-COOH is the correct answer, because in Lab during an extraction we must use NaHCO3 or NAOH to deprotonate an R-COOH group in order for it be soluble in water.

So this would be going against that if it was the right answer?

since R-OH would work without an extra deprotonating step....

So am I right or confused lol ?

 

[Charles_Darwin]

Dat Destroyer number 218 organic chemistry.....


I believe the most soluble will be R-OH , alcohol

But the book said it was R-COOH, Carboxylic Acid as the correct answer .....

I have a confusion now with the book saying that R-COOH is the correct answer, because in Lab during an extraction we must use NaHCO3 or NAOH to deprotonate an R-COOH group in order for it be soluble in water.

So this would be going against that if it was the right answer?

since R-OH would work without an extra deprotonating step....

So am I right or confused lol ?

Interesting.... I'd personally go straight to the RCOOH because I'd assume more oxygens = more hydrogen bonding in water

 

[DentalNucleicAcid]

^ I agree with that. I also want to add that RCOOH would be more soluble because not only does it have an OH for H-bonding like alcohol does, but the double bond can also resonate, creating an additional dipole that alcohol does not have, thus making it more water soluble.

For the lab thing, the insolubility of RCOOH comes from the fact that the carboxylic acids that are used have very big R groups, which make the whole entire molecule insoluble even though there is a soluble COOH group at the end. So don't confuse the lab technique with the general idea of a carboxy acid. They're soluble, but just not with long R groups. In any case, if you had to choose between a carboxy acid and an alcohol with an equivalent R group, the carboxy acid would win.

 

[DAT Destroyer]

Dat Destroyer number 218 organic chemistry.....


I believe the most soluble will be R-OH , alcohol

But the book said it was R-COOH, Carboxylic Acid as the correct answer .....

I have a confusion now with the book saying that R-COOH is the correct answer, because in Lab during an extraction we must use NaHCO3 or NAOH to deprotonate an R-COOH group in order for it be soluble in water.

So this would be going against that if it was the right answer?

since R-OH would work without an extra deprotonating step....

So am I right or confused lol ?

For # 218....... NOT a chance. The alcohol contains 5 carbons and would be sparingly soluble at best. The acid not only has an additional Oxygen, but more extensive hydrogen bonding can occur.

Hope this helps.

Dr. Romano

 

[Mrhyde]

For the lab thing, the insolubility of RCOOH comes from the fact that the carboxylic acids that are used have very big R groups, which make the whole entire molecule insoluble even though there is a soluble COOH group at the end. So don't confuse the lab technique with the general idea of a carboxy acid. They're soluble, but just not with long R groups. In any case, if you had to choose between a carboxy acid and an alcohol with an equivalent R group, the carboxy acid would win.

I see that makes sense thank you everyone who posted for clearing that up for me as i was confused with the lab part relating to it. It did not occur to me that the R-COOH was only a problem if the R- was a long chain , but now i understand that if its a short chain then there is no problem dissolving in water.

Thank you