Draw all possible structures for a compound with molecular formula C4H8O that exhibits a broad signal between 3200 and 3600 cm-1 in its IR spectrum and does not contain any signals between 1600 and 1850 cm-1.

Cyclic butanol , 1 cyclopropyl methanol, 1-methyl cyclo propan-1-ol.

Explanation:

IR wave-number of O-H bond =

The intensity of the signal is broad and strong.

IR wave number of C=C bond =

The intensity of the signal is weak.But for the given chemical formula it didn't show any signal in its IR spectrum.This means that no unsaturation is present.

IR wave number of C=O bond =

The intensity of the signal is broad and strong.But for the given chemical formula it didn't show any signal in its IR spectrum. This means that no C=O is present in the compound

For the given formula the possible structures wil be:

As we know from the I.R. data that no unsaturation is present which indicates that the given compound has cyclic structure.

The possible structures are attached in an image.

c-14 is carbon-14, or radiocarbon.   it is a radioactive isotope of carbon with an atomic nucleus containing 6 protons and 8 neutrons.