Given here are \({ }^{1} \mathrm{H}-\mathrm{NMR}\) and \({ }^{13} \mathrm{C}\)-NMR
spectral data for nine compounds. Each compound shows strong absorption
between 1720 and \(1700 \mathrm{~cm}^{-1}\) and strong, broad absorption over
the region \(2500-3300 \mathrm{~cm}^{-1}\). Propose a structural formula for
each compound. Refer to Appendices 4,5, and 6 for spectral correlation tables.
(a) \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}_{2}\)
$$
\begin{array}{|cc|}
\hline{ }^{1} \text { H-NMR } & { }^{13} \text { C-NMR } \\
\hline 0.94(\mathrm{t}, 3 \mathrm{H}) & 180.71 \\
1.39(\mathrm{~m}, 2 \mathrm{H}) & 33.89 \\
1.62(\mathrm{~m}, 2 \mathrm{H}) & 26.76 \\
2.35(\mathrm{t}, 2 \mathrm{H}) & 22.21 \\
12.0(\mathrm{~s}, 1 \mathrm{H}) & 13.69 \\
\hline
\end{array}
$$
$$
\begin{aligned}
&\text { (b) } \mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}_{2}\\\
&\begin{array}{|cr|}
\hline{ }^{1} H-N M R & { }^{13} C-N M R \\
\hline 1.08(\mathrm{~s}, 9 \mathrm{H}) & 179.29 \\
2.23(\mathrm{~s}, 2 \mathrm{H}) & 47.82 \\
12.1(\mathrm{~s}, 1 \mathrm{H}) & 30.62 \\
& 29.57 \\
\hline
\end{array}
\end{aligned}
$$
$$
\begin{aligned}
&\text { (c) } \mathrm{C}_{5} \mathrm{H}_{8} \mathrm{O}_{4}\\\
&\begin{array}{|cc|}
\hline{ }^{1} \text { H-NMR } & { }^{13} \mathrm{C}-\mathrm{NMR} \\
\hline 0.93(\mathrm{t}, 3 \mathrm{H}) & 170.94 \\
1.80(\mathrm{~m}, 2 \mathrm{H}) & 53.28 \\
3.10(\mathrm{t}, 1 \mathrm{H}) & 21.90 \\
12.7(\mathrm{~s}, 2 \mathrm{H}) & 11.81 \\
\hline
\end{array}
\end{aligned}
$$
$$
\begin{aligned}
&\text { (d) } \mathrm{C}_{5} \mathrm{H}_{8} \mathrm{O}_{4}\\\
&\begin{array}{|cc|}
\hline{ }^{1} \mathrm{H}-\mathrm{NMR} & { }^{13} \mathrm{C}-\mathrm{NMR} \\
\hline 1.29(\mathrm{~s}, 6 \mathrm{H}) & 174.01 \\
12.8(\mathrm{~s}, 2 \mathrm{H}) & 48.77 \\
& 22.56 \\
\hline
\end{array}
\end{aligned}
$$
$$
\begin{aligned}
&\text { (e) } \mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O}_{2}\\\
&\begin{array}{|cc|}
\hline{ }^{1} \mathrm{H}-\mathrm{NMR} & { }^{13} \mathrm{C}-\mathrm{NMR} \\
\hline 1.91(\mathrm{~d}, 3 \mathrm{H}) & 172.26 \\
5.86(\mathrm{~d}, 1 \mathrm{H}) & 147.53 \\
7.10(\mathrm{~m}, 1 \mathrm{H}) & 122.24 \\
12.4(\mathrm{~s}, 1 \mathrm{H}) & 18.11 \\
\hline
\end{array}
\end{aligned}
$$
$$
\begin{aligned}
&\text { (f) } \mathrm{C}_{3} \mathrm{H}_{4} \mathrm{Cl}_{2} \mathrm{O}_{2}\\\
&\begin{array}{|cc|}
\hline{ }^{1} \text { H-NMR } & { }^{13} \mathrm{C}-\mathrm{NMR} \\
\hline 2.34(\mathrm{~s}, 3 \mathrm{H}) & 171.82 \\
11.3(\mathrm{~s}, 1 \mathrm{H}) & 79.36 \\
& 34.02 \\
& \\
\hline
\end{array}
\end{aligned}
$$
$$
\begin{aligned}
&\text { (g) } \mathrm{C}_{5} \mathrm{H}_{8} \mathrm{Cl}_{2} \mathrm{O}_{2}\\\
&\begin{array}{|cr|}
\hline{ }^{1} \text { H-NMR } & { }^{13} \text { C-NMR } \\
\hline 1.42(\mathrm{~s}, 6 \mathrm{H}) & 180.15 \\
6.10(\mathrm{~s}, 1 \mathrm{H}) & 77.78 \\
12.4(\mathrm{~s}, 1 \mathrm{H}) & 51.88 \\
& 20.71 \\
\hline
\end{array}
\end{aligned}
$$
$$
\begin{aligned}
&\text { (h) } \mathrm{C}_{5} \mathrm{H}_{9} \mathrm{BrO}_{2}\\\
&\begin{array}{|cr|}
\hline{ }^{1} H-N M R & { }^{13} \text { C-NMR } \\
\hline 0.97(\mathrm{t}, 3 \mathrm{H}) & 176.36 \\
1.50(\mathrm{~m}, 2 \mathrm{H}) & 45.08 \\
2.05(\mathrm{~m}, 2 \mathrm{H}) & 36.49 \\
4.25(\mathrm{t}, 1 \mathrm{H}) & 20.48 \\
12.1(\mathrm{~s}, 1 \mathrm{H}) & 13.24 \\
\hline
\end{array}
\end{aligned}
$$
$$
\begin{aligned}
&\text { (i) } \mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}_{3}\\\
&\begin{array}{|cc|}
\hline{ }^{1} \mathrm{H}-\mathrm{NMR} & { }^{13} \mathrm{C}-\mathrm{NMR} \\
\hline 2.62(\mathrm{t}, 2 \mathrm{H}) & 177.33 \\
3.38(\mathrm{~s}, 3 \mathrm{H}) & 67.55 \\
3.68(\mathrm{~s}, 2 \mathrm{H}) & 58.72 \\
11.5(\mathrm{~s}, 1 \mathrm{H}) & 34.75 \\
\hline
\end{array}
\end{aligned}
$$
