From 4-pentin-1-ol obtain:

SOLUTION:



[1] Oxidation of alcohol to aldehyde
[2] Carbon-carbon bond formation by magnesium organometallics
[3] Alcohol protonation
[4] Alcohol oxidation with Jones (You can also use CrO₃(py)₂)
[5] Markovnikov hydration of the alkyne, to form ketones