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Question 4

Compounds F\textbf{F}F and G\textbf{G}G are two structural isomers with the molecular formula C5H10\text{C}_5\text{H}_{10}C5​H10​.

Neither compound F\textbf{F}F nor G\textbf{G}G exhibits stereoisomerism.

The table below displays NMR and infrared (IR) spectroscopic data for both isomers.

Number of peaks in 1H NMR spectrumNumber of peaks in 13C NMR spectrumIR absorption peak at 1620–1680 cm−1F11NoG34Yes \begin{array}{|c|c|c|c|} \hline & \text{Number of peaks in } ^1\text{H NMR spectrum} & \text{Number of peaks in } ^{13}\text{C NMR spectrum} & \text{IR absorption peak at } 1620\text{--}1680\text{ cm}^{-1} \\ \hline \textbf{F} & 1 & 1 & \text{No} \\ \hline \textbf{G} & 3 & 4 & \text{Yes} \\ \hline \end{array} FG​Number of peaks in 1H NMR spectrum13​Number of peaks in 13C NMR spectrum14​IR absorption peak at 1620–1680 cm−1NoYes​​

Draw (or describe) the structures of F\textbf{F}F and G\textbf{G}G and explain how the spectral data provides evidence for your proposed structures.

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Analysis Questions

  1. A Level
  2. /Chemistry
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