Which of the following gives white precipitate with ammonical silver nitrate…

2016

Which of the following gives white precipitate with ammonical silver nitrate solution?

  1. A.

    C₂H₆ (Ethane)

  2. B.

    C₂H₄ (Ethylene)

  3. C.

    C₂H₂ (Acetylene)

  4. D.

    C₃H₆ (Propene)

Attempted by 2 students.

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Correct answer: C

Ammoniacal silver nitrate solution (Tollens'-type reagent, [Ag(NH₃)₂]NO₃) reacts specifically with terminal alkynes - hydrocarbons containing a carbon-carbon triple bond with at least one hydrogen atom attached directly to a triple-bonded (sp-hybridised) carbon. Because of the high s-character of the sp carbon, this hydrogen is weakly acidic and is readily displaced by Ag⁺ ions, forming an insoluble white precipitate of a silver acetylide (a metal alkynide). Alkanes and alkenes contain no such acidic hydrogen, so they do not react with this reagent.

Among the given compounds, Acetylene (HC≡CH, C₂H₂) is the only one with a carbon-carbon triple bond, and both of its terminal carbons carry a hydrogen atom attached directly to an sp carbon. These hydrogens are displaced by Ag⁺ from the ammoniacal silver nitrate solution, producing disilver acetylide (Ag-C≡C-Ag), which separates out as a white precipitate.

  • Ethane (C₂H₆): has only C-C and C-H single bonds (sp³ carbons); with no unsaturation and no acidic hydrogen, it does not react with ammoniacal silver nitrate.

  • Ethylene (C₂H₄): has a carbon-carbon double bond (sp² carbons), but its vinylic hydrogens are not acidic enough to be displaced by Ag⁺, so alkenes give no precipitate with this test.

  • Propene (C₃H₆): also has only a carbon-carbon double bond (sp² carbons) and no triple bond; like ethylene, it does not react with ammoniacal silver nitrate.

This white-precipitate test with ammoniacal silver nitrate identifies a terminal alkyne by its acidic, triple-bond-adjacent hydrogen. Acetylene's structure meets that requirement, so its terminal hydrogens are the ones displaced by Ag⁺ to form the white silver-acetylide precipitate.

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