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An unsaturated hydrocarbon X on ozonolysis gives A. Compound A when warmed with ammonical silver nitrate forms a bright silver mirror along the sides of the test tube. The unsaturated hydrocarbon X is:

1. CH3-C(CH3)=C(CH3)-CH3
2. CH3-C(CH3)=C(CH3)-cyclopropyl
3. HCC-CH2-CH3
4. CH3-CC-CH3

Correct answer: HCC-CH2-CH3

Solution

Oxidative ozonolysis of the terminal alkyne HC=C-CH2CH3 gives HCOOH (formic acid) plus propanoic acid. Formic acid contains a -CHO group and reduces Tollens' reagent, producing the silver mirror. The symmetrical alkene/alkyne options give only ketones or acetic acid, which do not.

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