Chapter 15: Q15-3P (page 455)
Draw structures corresponding to the following IUPAC names:
(a) p-Bromochlorobenzene
(b) p-Bromotoluene
(c) m-Chloroaniline
(d) 1-Chloro-3,5-dimethylbenzene
Short Answer

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Chapter 15: Q15-3P (page 455)
Draw structures corresponding to the following IUPAC names:
(a) p-Bromochlorobenzene
(b) p-Bromotoluene
(c) m-Chloroaniline
(d) 1-Chloro-3,5-dimethylbenzene

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Bextra, a COX-2 inhibitor once used in the treatment of arthritis, contains an isoxazole ring. Why is the ring aromatic?
Bextra
The compound below is the product initially formed in a Claisen rearrangement (Section 18-4). This product is not isolated but tautomerizes to its enol form. Give the structure of the enol and provide an explanation as to why the enol tautomer is favored.

Draw all of the resonance forms for each. What patterns emerge?

The proton NMR spectrum for a compound with formula is shown below. The infrared spectrum has a strong band at . The normal carbon-13 NMR spectral results are tabulated along with the DEPT-135 and DEPT-90 information. Draw the structure of this compound.


Draw structures corresponding to the following names:
(a) 3-Methyl-1,2-benzenediamine
(b) 1,3,5-Benzenetriol
(c) 3-Methyl-2-phenylhexane
(d) o-Aminobenzoic acid
(e) m-Bromophenol
(f) 2,4,6-Trinitrophenol (picric acid)
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