Compound A has molecular formula C7H7X. Its 1H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C-NMR shows five signals. The mass spectrum of A shows a peak at m/z = 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively.
Compound A has molecular formula C7H7X. Its 1H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C-NMR shows five signals. The mass spectrum of A shows a peak at m/z = 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively.
- Identify what atom X is, explaining your reasoning
- Identify Compound A, explaining your reasoning
Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The 1H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively.
- Identify compound B, explaining your reasoning
Compound B is treated with sodium ethoxide to generate compound C. The 1H-NMR spectrum of C shows four signals - a triplet at 1.24 ppm, a singlet at 2.32 ppm, a quartet at 4.14 ppm, and a singlet at 7.42 ppm. The 13C-NMR spectrum of C shows seven signals.
- Identify compound C, explaining your reasoning
also give the names of the mechanisms for both of the two reactions (the reaction of A to generate B and of B to generate C), for example "electrophilic addition," "elimination," etc.
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