Sciencemadness Discussion Board

What is an alkylation?

RebeccaOlson - 9-3-2017 at 02:38

Hi guys, I have a reaction where dimethyl sulfate (which is apparently a methylating agent, so it alkylates on a methyl group) and sodium hydroxide is used to break a double bond and a single bond in half and changes the double bond to a single bond. How is that alkylating, which, as far as I know, adds something on to something else? Also, what's the use of the sodium hydroxide? Sorry if I seem really dumb. Thank you :)



[Edited on 9-3-2017 by RebeccaOlson]

RebeccaOlson - 9-3-2017 at 03:13

Actually, I got it. The nitrogen is methylated, then it's hydrolized.

CuReUS - 9-3-2017 at 03:19

its basically the forster-decker method for synthesis of secondary amines -https://en.wikipedia.org/wiki/Forster%E2%80%93Decker_method.The first step ,which is the formation of the schiff's base has already been done in the above compound.The dimethyl sulphate or any other alkylating agent adds an alkyl group(in this case a methyl group) to the imine formed,which is then hydrolysed to give the secondary amine.Adding a base(NaOH) allows the hydrolysis and free-basing to be done simultaneously in one step since the base will mop up any acid formed during the hydrolysis and prevent the acid from forming a salt with the amine.

[Edited on 10-3-2017 by CuReUS]

RebeccaOlson - 9-3-2017 at 06:06

Thank you sooo much CuReUS <3