The labels on a shipment of the five chemicals A- below were washed off by accid

Question

The labels on a shipment of the five chemicals A- below were washed off by accident when the del J truck when, through a truck wash with the doors open. A clever student took infrared spectra of each of the resulting unknown Unknown #1 had a strong, broad IR absorption of 3400 - 3600# cm-l, and no absorptions between 1600 and 2900 ' cm-1. Unknown #2 had a strong absorption at 1680 cm-1 arid no absorptions above 3100 cm-1. what are the structures of the unknowns? Explain your choice by indicating why you chose them and not the other three structures.

Explanation / Answer

Unknown #1 is B. i.e. cyclohexanol.

broad IR absorption at 3400-3600cm-1 is of O-H stretching.
Unknown #2 is C.

strong absorption at 1680cm-1 is of C=O stretching, this low value is due to conjugation.

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