In IR spectrum, recorded neat, a compound shows a strong and broad band at 3300 cm−1. The band becomes sharp and shifts to 3600 cm−1 when the spectrum is recorded in CCl4 at high dilution. This proves that the compound has

1
OH group, which is involved in intramolecular H-bonding
2
OH group, which is involved in intermolecular H-bonding
3
a terminal alkyne group
4
OH group, present in severely sterically hindered environment

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