Chapter 14: Q43P (page 527)
How can you use \(^{\bf{1}}{\bf{H}}\) NMR spectroscopy to distinguish between \({\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{ = C}}\left( {{\bf{Br}}} \right){\bf{C}}{{\bf{O}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{3}}}\)and methyl (E)-3-bromopropenoate, \({\bf{BrCH = CHC}}{{\bf{O}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{3}}}\)?
Short Answer
Step by step solution
1H NMR spectroscopy
Organic structures can be determined using the 1H NMR spectroscopy. In this, the environment of protons is determined.
Splitting of signals in the \(^{\bf{1}}{\bf{H}}\) NMR spectroscopy
The geminal and trans protons split into doublets. The formula used to determine the peaks is n+1, where n is the number of protons.
Explanation
The compound\({\rm{C}}{{\rm{H}}_{\rm{2}}}{\rm{ = C}}\left( {{\rm{Br}}} \right){\rm{C}}{{\rm{O}}_{\rm{2}}}{\rm{C}}{{\rm{H}}_{\rm{3}}}\)has geminal protons,\({{\rm{H}}_{\rm{a}}}\)and\({{\rm{H}}_{\rm{b}}}\), that split into a doublet.
The compound \({\rm{BrCH = CHC}}{{\rm{O}}_{\rm{2}}}{\rm{C}}{{\rm{H}}_{\rm{3}}}\) has trans protons, \({{\rm{H}}_{\rm{a}}}\) and \({{\rm{H}}_{\rm{b}}}\), that also split into a doublet.
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