Q.
The major product o f the following reaction is
Solution:
It is the first step of Gabriel- phthalimide synthesis. The
hydrogen bonded to nitrogen is sufficiently acidic due to two
a-carbonyls.
The conjugate base formed above act as nucleophile in the
subsequent step of reaction. As shown above, the nucleophile
exist in three resonating form, one may think of oxygen being
the donor atom in the nucleophilic attack. However, nitrogen act
as donor as it is belter donor than oxygen
Bromine is not substituted in the above reaction as it is in
resonance with benzene ring giving partial double bond
character to C Br bond, hence difficult to break.
