Ethanamine (CH3CH2NH2) experiences a rapid exchange of NH2 protons. How do you predict that this affects the 1H NMR spectrum? of ethanamine?
◦ Like many other molecules with NH2, ethanamine is highly unstable and produces a variable proton NMR signal.
◦ The effects on the NMR spectrum depend on whether an oxygen is nearby, so it is impossible to predict whether the rapid exchange would affect their signal.
◦ The NH2 protons should produce a standard NMR signal despite this rapid exchange.
◦ NH2 protons are exchanged too rapidly for splitting to occur, so a singlet is produced.
◦ Like other molecules with nitrogen, the electronegativity of nitrogen prevents NH2 protons from producing a signal.