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Question #44936

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The Question

An amount of 0.550.55 moles of ethyl bromide (\ce{C2H5Br}) is subjected to ammonolysis using a controlled amount of ethanolic ammonia at 298298 K. The reaction goes to completion, yielding a mixture of primary (1∘1^\circ), secondary (2∘2^\circ), and tertiary (3∘3^\circ) amines in a 4:2:14:2:1 molar ratio. (Assume no quaternary ammonium salt is formed).

The entire amine mixture is then treated with an excess of Hinsberg reagent (\ce{C6H5SO2Cl}) in the presence of aqueous \ce{KOH}. The resulting reaction mixture is extracted with diethyl ether to separate it into an aqueous layer (A) and an organic layer (B).

Layer B is then thoroughly washed with dilute aqueous \ce{HCl}, and the ether is evaporated to leave behind an organic compound (C).

Calculate the mass of compound (C) obtained. (Molar masses in g/mol: H=1, C=12, N=14, O=16, S=32)

Options

  • A.

    21.3 g

  • B.

    26.4 g

  • C.

    33.5 g

  • D.

    37.0 g

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Correct Answer

Step-by-Step Solution

Explanation

How the Examiner Thinks

Mechanism_Trap

Don't get tricked by the process! Learn the mechanical traps used in competitive exam questions.

Concepts Behind This Question

Ammonolysis Complexity|Hinsberg Reagent Selectivity

Why This Question Is Tricky

Common Mistakes

This problem tests the student's ability to track stoichiometry through a multi-step synthesis involving parallel reactions (ammonolysis) and differential solubility (Hinsberg test).

The 'hidden variable' is the stoichiometric consumption of the alkyl halide: students often mistakenly assume the 4:2:1 ratio applies to the total moles of amines equaling the moles of alkyl halide, ignoring that secondary and tertiary amines consume multiple equivalents of the alkyl group.

Furthermore, it tests the precise chemical behavior of tertiary amines in the Hinsberg test—recognizing that they remain unreacted in the organic layer but are subsequently removed by the acidic wash, isolating the secondary sulfonamide.

Quick Facts About This Question

Question Information

SubjectChemistry
ChapterAmines - Class 12
ConceptAmmonolysis Complexity
Difficulty8
Cognitive Load7
Target Solve Time160 sec
AccessFree