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Dolbier HW Solutions 603 - 697 PHENOLS 24.30(a The...

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24.30 ( a ) The molecular formula of the compound (C 9 H 12 O) tells us that it has a total of four double bonds and rings (index of hydrogen de fi ciency 4). The prominent peak in the infrared spec- trum is the hydroxyl absorption of an alcohol or a phenol at 3300 cm 1 . Peaks in the 110 160 ppm region of the 13 C NMR spectrum suggest an aromatic ring, which accounts for six of the nine carbon atoms and all its double bonds and rings. The presence of four peaks in this region, two of which are C and two CH, indicates a para- disubstituted aromatic derivative. That the remaining three carbons are sp 3 -hybridized is indicated by the up fi eld absorptions at 15, 26, and 38 ppm. None of these carbons has a chemical shift below 40 ppm, and so none of them can be bonded to the hydroxyl group. Thus the hydroxyl group must be bonded to the aromatic ring. The compound is 4-propylphenol. ( b ) Once again the molecular formula (C 9 H 11 BrO) indicates a total of four double bonds and rings. The four peaks in the 110
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