Sommelet vs. Delepine

[Daphuk_up]

SWID, despite doing numerous searches and reading using both TFSE and google (as well as his organic chem books), still hasn't been able to understand the difference between these two reactions.

They start off the same...react an arylakyl-halide with hexamine to form the quaternary salt.  Then both reactions call for acid hydrolysis, yet they each claim a distinctly different product.  The only clue that SWID has been able to find is where the MERCK calls for "mild hydrolysis" in the Sommelet reaction.  Alluding, but not exactly clearly informative.

Can someone please post an example or reference of a Sommelet, and perhaps even explain the mechanistic difference between the two named reactions?  It would be ever so appreciated, SWID is quite confused.

EDIT:SWID noticed just now that the MERCK doesn't mention the use of acid...will just refluxing in plain water or 50% ethanol cause the hydrolysis of the quaternary compound?

[gsus]

...is the product and conditions, as you know. Hydrolysis ala Delepine gives the amine. Merck leaves a bit out. The Sommelet means the amine reacts with excess hexamine, the hydrolyzing agent in the end is water. see OS V, 668.

[Daphuk_up]

So, for instance, benzyl chloride reacts with hexamine to give benzyl amine (ala delepine), which in turn reacts with another molecule of hexamine to give an intermediate which undergoes hydrolysis by water to give the aldehyde?

So is it necessary then to use acid hydrolysis to go from the benzyl chloride-hexamine quaternary salt to benzyl amine, or does this also undergo hydrolysis in plain water?  If the acid is necessary, then wouldn't excess hexamine need be added after the 'delepine part', followed by heavy reflux?

Thanks gsus for the info.  

[moo]

See the document linked to

Post 381907

(Rhodium: "Hexamethylenetetramine (HMTA, Hexamine)", Chemistry Discourse). TFSE is the shit you know, what else could be there?

[Daphuk_up]

Thanks moo, exactly what SWID was looking for.  

What indeed.