Destroyer Orgo pg 31 #107, solubility question

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How is ethyl-benzene soluble in water??

How is 2-octanone soluble in water while 2-octaamine is not? Amine sounds far more soluble to me since it can do H-bonding.

If you look at the question, it asks you which compound is NOT soluble in water, but soluble in HCl or HBr. 2-octanamine is NOT water soluble because it has a long carbon chain (the rule of thumb is a carbon chain of 3 or longer on an amine is not water soluble). However, it is soluble in HCl or HBr, bc the amine group is more easily protonated, once protonated, it will become charged and become soluble in water.

I'm not sure where it says 2-octanone is soluble in water... but I would think it's not. But then again we could be referring to different versions of the Destroyer. I'm referring to the 2012 version. You should specify next time!

Originally Posted by TXpredent

If you look at the question, it asks you which compound is NOT soluble in water, but soluble in HCl or HBr. 2-octanamine is NOT water soluble because it has a long carbon chain (the rule of thumb is a carbon chain of 3 or longer on an amine is not water soluble). However, it is soluble in HCl or HBr, bc the amine group is more easily protonated, once protonated, it will become charged and become soluble in water.

I'm not sure where it says 2-octanone is soluble in water... but I would think it's not. But then again we could be referring to different versions of the Destroyer. I'm referring to the 2012 version. You should specify next time!

Well I am referring to 2012 as well. And I also read the solution explanation too. But Octanone, it's polar and incapable of forming h-bond. Ketones are less soluble than Amines because of this reason.

Originally Posted by clubwestpua

Well I am referring to 2012 as well. And I also read the solution explanation too. But Octanone, it's polar and incapable of forming h-bond. Ketones are less soluble than Amines because of this reason.

I think i'd agree with you there. But I'm confused about your question? ethyl benzene and octanone are both insoluble in water. And so is octanamine, unless treated with a strong acid.

ethyl benzene is not soluble in water!!!!! None are soluble in water since so many carbons. However as the question asks...for in ACID !!!!!! The amine can be protonated and made into the ammonium salt