In the study of rates of reaction with hydroxylamine, it was discovered that the
ID: 539320 • Letter: I
Question
In the study of rates of reaction with hydroxylamine, it was discovered that the imine starting material where X is a nitro group (-NO2) reacted 200 times faster at pH = 2 than the molecule in which the X is hydrogen. Considering most imines react optimally at a pH = 5, explain why this product is formed so much more quickly in the case of the nitro derivative. (HINT: 2 explanations exist-think about both nucleophiles and electrophiles.)
acid catalyst NH2 +HO-NH2 relative rate by subsititution X--NOg, 200 X=-HExplanation / Answer
Ans, NO2 is a powerful electron withdrawing group that makes the imine Carbon more electrophilic which leads the hydroxyl amine to react imine carbon very fast and second thing for the high reaction is that the (CH3)3 - NH+ is a very good leaving group.
In case H, the imine carbon is very less electrophilic and hence reaction will be slower.