[souro10]

Precisely. The mechanism you proposed isn't typical of SN₁ , is it?
If the water attacks the carbon before the bromide ion is completely detached, racemisation shouldn't have occurred. Inversion should have occurred.

[discodermolide]

So where are we now with this?

[souro10]

I was trying to make the point that, in the KCN case I posted in the first post of this thread, the reaction does not occur not because all alkyl halides are (wrongly) insoluble in water- and in fact some alkyl halides do undergo spontaneous solvolysis in water- but because the alkyl halides would prefer the organic solvent in preference to water, for entropic reasons. This point was never raised.

But if we directly dissolve the same alkyl halide in water and raise the temperature to moderate levels, the reaction will occur, even if a bit slow.

[curiouscat]

I did state some time back that small alkyl halides like Ethylbromide are soluble in water.

Solubility is less than 1% w/w. I'd call that slightly soluble but I'm not sure what accepted terminology is.

 

[souro10]

Yeah, approximately 9.1 grams/l of water.
That's low solubility according to me too, but then, its still soluble even if in small proportions. There is a difference between insolubility and low solubility. Low soluble means soluble- although it doesn't describe how much soluble it is. Insolubility means not soluble.

Ethylene too has low solubility in water. If ethylene reacts with water with a bit of acid mixed with it because the acid loves the electrons of the pi bond, then tertiary halides should react with CN- in water too, although there should be a significant amount of tertiary butyl alcohol.

[souro10]

I didn't know wood and sand are at all soluble in water in any proportion! But we're deviating from the topic.
It'll be helpful if someone commented on the KCN case.

EDIT: The above post was a reply to a post by Curiouscat that almost everything is soluble in some proportions, which I now find is deleted.

[curiouscat]

I didn't know wood and sand are at all soluble in water in any proportion! But we're deviating from the topic.
It'll be helpful if someone commented on the KCN case.

EDIT: The above post was a reply to a post by Curiouscat that almost everything is soluble in some proportions, which I now find is deleted.

Yes, that's right and I still stand by that statement.

Reason I deleted that post is that I'm afraid, by adding any fodder to the fire I'm only encouraging a troll here. Hence I will refrain from any further comments in this thread no matter how tempting.  Have fun.

[souro10]

I think the usual people here mostly avoid contexts and cross questions about a topic.
A very unpleasant experience in this forum, thanks to some of the Senior members.
I'm leaving this forum, thank you. Have fun too.