To make 2,4,6-trimethylbenzyl chloride, I have to use 1,3,5-trimethylbenzene and react it with formaldehyde and HCl.

Ive gotten started but now im stuck.

 

So the H-Cl protonates the formaldehyde making that carbon delta positive. this carbon can now be attacked by one of the carbons of the 1,3,5-trimethylbenzene at any of the available spots. creating an OH where the Cl needs to be. How do i get rid of the OH now in order for the Cl to attack?

 

I was thinking of protonating the OH with another molecule of HCl and then allowing an SN2 reaction to take place so the Cl can attack and replace the OH.

 

But i have a feeling that I've done something wrong?

wait so if right now you have 1,3,5-trimethylbenzyl hydroxide, then yeah of course simply adding hcl to it should get you 1,3,5-trimethylbenzyl chloride + water. OH radical is a stronger oxidizer than Cl so it would want to be with that hydrogen from hcl more than that hydrocarbon benzyl whatever.

 

but idk how that whole delta formaldehyde protonation thing works. why would carbons attack carbons? idk.

Edited July 12, 200916 yr by onequestion

protonating the O of the formaldehyde (by HCl) causes the carbon to be more vulnerable to attack by one of the pi electrons from the 1,3,5-trimethylbenzene.