Exams › JEE Advanced › Chemistry

A sequence of reactions is carried out: phthalic acid is converted to phthalic anhydride using P2O5; phthalic anhydride reacts with NH3 to give phthalimide; phthalimide treated with aqueous KOH yields potassium phthalimide; finally, potassium phthalimide reacts with p-bromobenzyl chloride to give an N-substituted product. Which named reaction does this sequence represent?

1. Cannizzaro reaction
2. Haloform reaction
3. Wolff-Kishner reduction
4. Gabriel phthalimide synthesis

Correct answer: Gabriel phthalimide synthesis

Solution

The Gabriel phthalimide synthesis uses the potassium salt of phthalimide as a nucleophile that reacts with alkyl halides to give N-alkylphthalimide; subsequent hydrolysis gives primary amines. The sequence described matches this exactly.

Related JEE Advanced Chemistry questions

• Which of the following transformations represents the correct reduction of an amide using LiAlH4?
• Among arylamines, alkylamines, and ammonia, the order of basic strength is:
• When C₆H₅NH₂ reacts with AlCl₃ and CH₃Cl, no reaction occurs. What can be inferred about the directing nature of the (-NH₂, AlCl₃) substituent?
• Diazomethane is capable of transferring a methyl group to certain functional groups. Compound IV contains an enolic —OH group, so it can undergo methylation by CH₂N₂. Which of the following is correct?
• In the reaction sequence: A --[SnCl2/HCl]--> B --[NaNO2/HCl, 0 deg C]--> C --[H2O/heat]--> C6H5OH. Identify compounds A, B, and C.
• Which of the following chemical tests can specifically identify a primary amino (-NH2) group in an organic compound?

⚔️ Practice JEE Advanced Chemistry free + battle 1v1 →