|
Summary
|
|
Step 1: An acid/base reaction. Deprotonation of the imide N-H proton by the base, hydroxide. This proton is more acidic than a simple amine due to the resonance stabilisation by the two adjacent C=O groups. This generates a strong nucleophile, the -ve N. |
|
Step 2: The N nucleophile attacks the electrophilic C of the alkyl halide displacing the bromide and creating the new C-N bond. This product can be compared to an N-alkyl amide. |
|
Step
3: The imide can be cleaved via a mechanism analogous to that of amides. Hydrolysis creates the dicarboxylic acid and the required amine. |
|
© Dr. Ian Hunt, Department of Chemistry |