Question

Difficulty: MediumAlkenes and Alkynes: Preparation, Reactions, and Unsaturation Tests

Match each chemical process or reagent involving alkenes and alkynes in Column A with its corresponding chemical observation or primary product in Column B.

  • Hydrolysis of calcium carbide (CaC2\text{CaC}_2)Laboratory preparation of ethyne gas (C2H2\text{C}_2\text{H}_2)
  • Treatment of propene (CH3CH=CH2\text{CH}_3\text{CH}=\text{CH}_2) with bromine in CCl4\text{CCl}_4Decolorization of the reddish-brown solution due to halogen addition across the double bond
  • Treatment of but-1-yne (CH3CH2CCH\text{CH}_3\text{CH}_2\text{C}\equiv\text{CH}) with ammoniacal AgNO3\text{AgNO}_3 solutionFormation of a white precipitate of silver alkynide due to the presence of an acidic terminal hydrogen
  • Treatment of but-2-yne (CH3CCCH3\text{CH}_3\text{C}\equiv\text{CCH}_3) with ammoniacal AgNO3\text{AgNO}_3 solutionNo visible reaction because of the absence of an acidic hydrogen on the triply-bonded carbon

Answer

The correct pairing links calcium carbide hydrolysis to ethyne gas preparation, propene with bromine in carbon tetrachloride to reddish-brown decolorization, but-1-yne with ammoniacal silver nitrate to white precipitate formation, and but-2-yne with ammoniacal silver nitrate to no visible reaction.
Hydrolysis of calcium carbide is a standard laboratory preparation of ethyne gas. Electrophilic addition of bromine across the double bond of propene decolorizes the reddish-brown bromine solution, demonstrating general unsaturation. Ammoniacal silver trioxonitrate(V) reacts specifically with terminal alkynes like but-1-yne because of their acidic terminal hydrogens to form a white silver alkynide precipitate, whereas internal alkynes like but-2-yne lack a terminal acidic hydrogen and show no reaction.

Step-by-Step Solution

1
Identify the preparation method for ethyne
Calcium carbide reacts with water according to CaC2+2H2OC2H2+Ca(OH)2\text{CaC}_2 + 2\text{H}_2\text{O} \rightarrow \text{C}_2\text{H}_2 + \text{Ca(OH)}_2, yielding ethyne gas.
This is the primary laboratory method for generating ethyne.
2
Evaluate the reaction testing for general unsaturation in propene
Bromine in CCl4\text{CCl}_4 adds across the carbon-carbon double bond of propene to form 1,2-dibromopropane.
The consumption of molecular bromine causes the reddish-brown color of the solution to discharge.
3
Distinguish between terminal and internal alkynes using ammoniacal silver trioxonitrate(V)
But-1-yne possesses a terminal CC-H\text{C}\equiv\text{C-H} bond with an acidic proton that forms a white silver alkynide precipitate, whereas internal but-2-yne lacks terminal hydrogen atoms and gives no precipitate.
Ammoniacal AgNO3\text{AgNO}_3 selectively reacts only with terminal alkynes based on terminal hydrogen acidity.

Key Concept

Unsaturation testing, ethyne synthesis, and differentiation of terminal from internal alkynes
Estimated Time:1m 30s
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