everyone. In the following reaction, what is it that causes NaOH to attack either bond A or B over all the other bonds available? Subsequently, why does NaOH not continue with bond B once bond A has been reacted with? Thanks!
closed as off-topic by Mithoron, Tyberius, Todd Minehardt, airhuff, M. Farooq Jun 19 at 5:05
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The above reaction is a modification of Gabriel phtahlimide synthesis from here:
This procedure, known as the Gabriel synthesis, can be used to advantage in aminating bromomalonic esters.Since the phthalimide substituted malonic ester has an acidic hydrogen (colored orange), activated by the two ester groups, this intermediate may be converted to an ambident anion and alkylated. Finally, base catalyzed hydrolysis of the phthalimide moiety and the esters.
The reaction you show is base catalyzed hydrolysis of the phthalimide shown in the link.
The mechanism of this reaction is shown below:
Both amide bonds(2 to 3 and 5 to 6) cleaves.