You will be provided with spectral data for an unknown compound. Your task is to

Question

You will be provided with spectral data for an unknown compound. Your task is to identify the unknown by analyzing the material provided for the unknown and draw out the structure.

When you have identified your sample, you will write a report. The report should contain a description of the sample and a detailed account of how you identified your two unknowns. You need to discuss the assignment of structure based on your spectral data. ALL MAJOR PEAKS in all spectra must be assigned. Consider all possible structures for your unknown, and rule out any likely candidates using spectral data. You must provide a lucid and convincing case for the assignment of each unknown. You should also provide melting points for unknown solids.

Compound: C8H8O

O Slgma-Aldich Co. ALL RUGHTS RESERVED 300 MHz 'H NMR In CDCI3 1.2 1.1 1.0 0.9 0.8 0.7 0.6 0.5 0.4 0.3 0.2 0.1 C2H3O 5 H'S riplet triple oromatic rin o.SCm o. bcm O, 6 0.0 8 6 4 3 2 2(8) t2 to0- CQ N 2 a| tocD

Explanation / Answer

Spectral analysis and identification of compound

IR spectrum shows peaks at,

3000-3100 cm-1 for sp2 =C-H stretch

1500 cm-1 for C=C stretch

1H NMR shows,

3.2 ppm (triplet, 2H) for CH2 between CH2 and Br

4.5 ppm (triplet, 2H) for CH2 between CH2 and O

6.8-7.2 ppm peaks for aromatic (5H)

13C NMR shows,

30 ppm for CH2 carbon next to Br

70 ppm for CH2 carbon next to oxygen

110, 120, 125, 128 ppm peaks for aromatic carbons

Possible structure,

C6H5-O-CH2-CH2-Br

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