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JEE Chemistry 2026 Question with Solution

Consider the following reactions giving major product. Identify the correct reaction.

Four organic reaction schemes labeled 1 to 4, including Gabriel synthesis, carbylamine reaction, nitration of acetanilide, and Hofmann bromamide reaction with reagents and products shown.
  • A

    Reaction 1

  • B

    Reaction 2

  • C

    Reaction 3

  • D

    Reaction 4

Answer

Correct answer:D

Step-by-step solution

Standard Method

Given: Four reactions are shown and we must identify which one gives the stated major product.

Find: The correct reaction.

Concept: The correct reaction is identified by checking whether the reactants, reagents, and named reaction are chemically consistent with the product formed.

Reaction (1): Potassium phthalimide reacting with an aryl halide, followed by heat and hydrolysis, is shown to give aniline. This resembles Gabriel phthalimide synthesis, but Gabriel synthesis works efficiently for alkyl halides, not aryl halides. Aryl halides do not undergo SN2S_N2 substitution easily.

Therefore, Reaction (1) is incorrect.

Reaction (2): Benzylamine is treated with CHCl3/KOH\mathrm{CHCl_3/KOH}, followed by reduction. CHCl3/KOH\mathrm{CHCl_3/KOH} gives the carbylamine reaction with a primary amine, producing an isocyanide. The product does not revert back to the original amine upon reduction in the manner shown.

Therefore, Reaction (2) is incorrect.

Reaction (3): Acetanilide undergoes nitration using HNO3/H2SO4\mathrm{HNO_3/H_2SO_4}. The NHCO-NHCO- group is ortho-para directing. Nitration gives a mixture of ortho- and para-nitroacetanilide, with the para isomer as the major product. The reaction as drawn does not correctly represent the major product distribution.

Therefore, Reaction (3) is incorrect.

Reaction (4):

CH3CH2CONH2+Br2+4KOHΔCH3CH2NH2+2KBr+K2CO3+2H2O\mathrm{CH_3CH_2CONH_2 + Br_2 + 4KOH \xrightarrow{\Delta} CH_3CH_2NH_2 + 2KBr + K_2CO_3 + 2H_2O}

This is the Hofmann bromamide reaction. In this reaction, an amide is converted into a primary amine with the loss of one carbon atom. Here, propionamide CH3CH2CONH2\mathrm{CH_3CH_2CONH_2} gives ethylamine CH3CH2NH2\mathrm{CH_3CH_2NH_2}, which matches the expected product exactly.

Therefore, Reaction (4) is correct.

Conclusion: The correct option is D.

Common mistakes

  • Confusing Gabriel phthalimide synthesis with substitution on aryl halides. Gabriel synthesis works for alkyl halides, while aryl halides generally do not undergo SN2S_N2 substitution. Check the nature of the halide before applying the named reaction.

  • Assuming CHCl3/KOH\mathrm{CHCl_3/KOH} can regenerate the same amine after reduction. This reagent combination gives the carbylamine reaction to form an isocyanide from a primary amine. Identify the actual intermediate and expected transformation instead of matching only the starting and ending amines.

  • Forgetting that the NHCO-NHCO- group is ortho-para directing in electrophilic substitution. Nitration of acetanilide gives mainly the para product but also the ortho product. Consider major product distribution rather than assuming a single arbitrary nitration product.

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