Question
Which alkyne would you start with to Prepare $\text{CH}_3-\text{CH}_2-\text{CH}_2-\text{CO}-\text{CH}_3?$

Answer

$\text{HC}\equiv\text{C}-\text{CH}_2-\text{CH}_2-\text{CH}_3+\text{H}_2\text{O}\xrightarrow[\text{HgSO}_4]{\text{H}_2\text{SO}_4}\\ \ \ \ \ \ \ \ \ \ _\text{Pent-1-yne}$$\ \ \ \ \ \ \ \ \ \ \ \ \ \text{OH}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\\text{H}_2\text{C}=\text{C}-\text{CH}_2-\text{CH}_2-\text{CH}_3\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{O}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ ||\\\rightleftharpoons\text{CH}_3-\text{C}-\text{CH}_2-\text{CH}_2-\text{CH}_3\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ _{\text{Pentan-2-one}}$

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