morsagh
Hazard to Others
Posts: 187
Registered: 20-2-2014
Member Is Offline
Mood: No Mood
|
|
Amines alkylation
What is easier to alkylate, primary amine or secondary? Like in reaction of for example ethylenediamine with bromomethane... there will most likely go
two methyls to one amine group or each amine will have one methyl group?
|
|
|
Metacelsus
International Hazard
Posts: 2539
Registered: 26-12-2012
Location: Boston, MA
Member Is Offline
Mood: Double, double, toil and trouble
|
|
Secondary, in general (as long as there isn't steric hindrance). The carbon atoms donate electron density, making the amine more nucleophilic.
|
|
|
Dr.Bob
International Hazard
Posts: 2750
Registered: 26-1-2011
Location: USA - NC
Member Is Offline
Mood: No Mood
|
|
Yes, if you alkylate ethylenediamine with 2 eq of bromomethane, then you would likely get mostly a tertiary amine on one side and the primary amine on
the other. There are tricks to getting monoalkylation, but they depend on the substrate, the alklylating agent, and more.
|
|
|
Nicodem
|
Thread Moved
28-5-2016 at 04:46 |
![[*]](images/xpblue/default_icon.gif){kind=icon}
