Single correct option
A hydrocarbon of formula gives a white precipitate with ammoniacal silver nitrate. On vigorous oxidative cleavage with hot alkaline followed by acidification, it gives a carboxylic acid that has a tertiary carbon atom, along with . The hydrocarbon is
- A. pent-1-yne
- B. 3-methylbut-1-yne
- C. pent-2-yne
- D. 2-methylbuta-1,3-diene
Show answer and solution
Answer: (B) 3-methylbut-1-yne
The white precipitate with shows a terminal alkyne (acidic C–H). Strong oxidation breaks the triple bond to give and . For the product acid to have a tertiary carbon, must be isopropyl: . This is 3-methylbut-1-yne. Pent-1-yne would give straight-chain butanoic acid, pent-2-yne is internal (no Tollens-type precipitate), and the diene is not an alkyne.
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