116
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:
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:
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Solution
The correct option is A
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:
As shown above, the nucleophile attacks the carbon bearing the better leaving group. In general, Bromine is a much better leaving group than Fluorine in nucleophilic substitutions. The Bromide might form KBr depending on the nature of the solvent.
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:
As shown above, the nucleophile attacks the carbon bearing the better leaving group. In general, Bromine is a much better leaving group than Fluorine in nucleophilic substitutions. The Bromide might form KBr depending on the nature of the solvent.
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