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Question

The following dihaloalkanes gives an N-(haloalkyl)phthalimide on reaction with one equivalent of the potassium salt of phthalimide. Deduce the structure of the phthalimide derivative formed:



Your Answer
A

Correct Answer
B

Your Answer
C

Your Answer
D

None of the above


Solution

The correct option is C


If you look at the potassium salt of phthalimide, the nitrogen part, with its negative charge, is a capable nucleophile. This charge is stabilized by the presence of the two electron-withdrawing carbonyl groups on either side of the nitrogen anion. But it is a nucleophile nevertheless:

In this problem, since there is just the one equivalent of the salt, the nucleophile attacks the less hindered carbon at position 1 of 1,3-dibromopentane. The Bromide might form KBr depending on the nature of the solvent.

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