Question

Propose a structure for an amine of formula \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{~N}\), which does not liberate a gas when treated with \(\mathrm{NaNO}_{2}\) and \(\mathrm{HCl}\), and has IR absorptions at \(917 \mathrm{~cm}^{-1}, 990 \mathrm{~cm}^{-1}\), and \(1640 \mathrm{~cm}^{-1}\), as well as an \(\mathrm{N}-\mathrm{H}\) absorption at \(3300 \mathrm{~cm}^{-1}\). The \({ }^{13} \mathrm{C}\) NMR spectrum is as follows: \(\delta 36.0, \delta 54.4, \delta 115.8, \delta 136.7\).

Propose a structure for an amine of formula C4H9N,

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Answer #1

IR frequency at 1640 is the presence of an alkene group (i.e. c-c). the structure is as follows:

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