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An unknown compound gives a molecular ion of m/z 70 in the

Chapter 12, Problem 46SP

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QUESTION:

An unknown compound gives a molecular ion of 𝑚/𝑧 70 in the mass spectrum. It reacts with semicarbazide hydrochloride to give a crystalline derivative, but it gives a negative Tollens test. The NMR and IR spectra follow. Propose a structure for this compound, and give peak assignments to account for the absorptions in the spectra. Explain why the signal at \(1790 \mathrm{~cm}^{-1}\) in the IR spectrum appears at an unusual frequency.

Equation transcription:

Text transcription:

1790{~cm}^{-1}

Questions & Answers

QUESTION:

An unknown compound gives a molecular ion of 𝑚/𝑧 70 in the mass spectrum. It reacts with semicarbazide hydrochloride to give a crystalline derivative, but it gives a negative Tollens test. The NMR and IR spectra follow. Propose a structure for this compound, and give peak assignments to account for the absorptions in the spectra. Explain why the signal at \(1790 \mathrm{~cm}^{-1}\) in the IR spectrum appears at an unusual frequency.

Equation transcription:

Text transcription:

1790{~cm}^{-1}

ANSWER:

Solution 46SP

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