Chapter 21: Problem 5
Write names for these compounds. (a) (b) (c) (d)
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When warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and rearrangement to give 2 -phenylpropanal. (a) Propose a mechanism for this example of a pinacol rearrangement (Section 10.7). (b) Account for the fact that 2-phenylpropanal is formed rather than its constitutional isomer, 1-phenyl-1-propanone.
Propose a structural formula for each compound given these NMR data. (a) \(\mathrm{C}_{9} \mathrm{H}_{9} \mathrm{BrO}\) (b) \(\mathrm{C}_{\mathrm{g}} \mathrm{H}_{9} \mathrm{NO}\) (c) \(\mathrm{C}_{9} \mathrm{H}_{9} \mathrm{NO}_{3}\) $$ \begin{array}{lc} \hline{ }^{1} \text { H-NMR } & { }^{13} \text { C-NMR } \\ \hline 1.39(\mathrm{t}, 3 \mathrm{H}) & 165.73 \\ 4.38(\mathrm{q}, 2 \mathrm{H}) & 131.56 \\ 7.57(\mathrm{~d}, 2 \mathrm{H}) & 131.01 \\ 7.90(\mathrm{~d}, 2 \mathrm{H}) & 129.84 \\ & 127.81 \\ & 61.18 \\ & 14.18 \\ \hline \end{array} $$ $$ \begin{array}{lc} \hline{ }^{1} \text { H-NMR } & { }^{13} \text { C-NMR } \\ \hline 2.06(\mathrm{~s}, 3 \mathrm{H}) & 168.14 \\ 7.01(\mathrm{t}, 1 \mathrm{H}) & 139.24 \\ 7.30(\mathrm{~m}, 2 \mathrm{H}) & 128.51 \\ 7.59(\mathrm{~d}, 2 \mathrm{H}) & 122.83 \\ 9.90(\mathrm{~s}, 1 \mathrm{H}) & 118.90 \\ & 23.93 \\ \hline \end{array} $$ $$ \begin{array}{cc} \hline{ }^{1} \text { H-NMR } & { }^{13} \text { C-NMR } \\ \hline 2.10(\mathrm{~s}, 3 \mathrm{H}) & 168.74 \\ 7.72(\mathrm{~d}, 2 \mathrm{H}) & 166.85 \\ 7.91(\mathrm{~d}, 2 \mathrm{H}) & 143.23 \\ 10.3(\mathrm{~s}, 1 \mathrm{H}) & 130.28 \\ 12.7(\mathrm{~s}, 1 \mathrm{H}) & 124.80 \\ & 118.09 \\ & 24.09 \\ \hline \end{array} $$
Which compound gives a signal in the \({ }^{1} \mathrm{H}\)-NMR spectrum with a larger chemical shift, furan or cyclopentadiene? Explain.
Show how to convert 1-phenylpropane into the following compounds. In addition to this starting material, use any necessary inorganic reagents. Any compound synthesized in one part of this problem may be used to make any other compound in the problem. (a) (b) (c) (d) (e) (f) (g) (h) (i)
Compound \(\mathrm{A}\left(\mathrm{C}_{9} \mathrm{H}_{12}\right)\) shows prominent peaks in its mass spectrum at \(m / z 120\) and 105 . Compound \(\mathrm{B}\) (also \(\mathrm{C}_{9} \mathrm{H}_{12}\) ) shows prominent peaks at \(m / z 120\) and 91 . On vigorous oxidation with chromic acid, both compounds give benzoic acid. From this information, deduce the structural formulas of compounds \(\mathrm{A}\) and \(\mathrm{B}\).
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