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Propyne and propene can be distinguished by:
A. Conc. H2SO4
B. Br2 in CCl4.
C. Dil. KMnO4
D. AgNO3 in ammonia.

Answer
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Hint: Silver nitrate in ammonia is actually Tollen’s reagent. It also reacts with acidic hydrogens to give precipitates.

Complete step by step answer:
To get the answer, let us check each reaction one by one:
Conc. H2SO4:
Propyne on reaction with conc. H2SO4 produces a ketone.

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Propene on reaction with conc. H2SO4 produces alcohol.

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Ketone and alcohol can’t be distinguished at this condition without adding any other reagent. Hence, it is not the correct option.

Br2]in[CCl4:
Propyne on reaction with Br2 in CCl4 produces a vicinal dibromo alkene whereas propene on reaction with Br2 in CCl4 produces a vicinal dibromo alkane.

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Hence, the two compounds can’t be distinguished by this process.


Dil. KMnO4:
Propynes on reaction with Dil. KMnO4 produce -ketoacid.
Propene on reaction with Dil. KMnO4 produce a vicinal diol.
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Hence, the two compounds cannot be distinguished by this method also.
AgNO3 in ammonia:
Propyne on reaction with AgNO3 in ammonia produces a white precipitate, while propene does not show any reaction with the Tollen’s reagent.

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This is due to the fact that Tollen’s reagent reacts with an acidic hydrogen forming a precipitate like in a propyne. The hydrogen which is replaced is very acidic due to high electronegativity of an sp hybridized carbon.

Hence, this reagent can be used to distinguish between a propyne and a propene.

Therefore, the correct answer is (D) AgNO3 in ammonia.

Note: When an alkyne is reacted with conc. Sulphuric acid, ketone is formed by the Markovnikov addition of -OH, followed by the rearrangement of the alcohol formed from enol form to keto.