Chapter 14: Q51P (page 527)
a. How many signals does dimethyl fumarate (\({\bf{C}}{{\bf{H}}_{\bf{3}}}{{\bf{O}}_{\bf{2}}}{\bf{CCH = CHC}}{{\bf{O}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{3}}}\) with a trans C=C) exhibit in its \(^{{\bf{13}}}{\bf{C}}\) NMR spectrum?
b. Draw the structure of an isomer of dimethyl fumarate that has each of the following number of signals in its \(^{{\bf{13}}}{\bf{C}}\) NMR spectrum:\(\left( {\bf{1}} \right)\) three; \(\left( {\bf{2}} \right)\) four; \(\left( {\bf{5}} \right)\) five
Short Answer
a.
b.
Step by step solution
Dimethyl fumarate
\(^{{\bf{13}}}{\bf{C}}\)The dimethyl fumarate has two\({\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{C}}{{\bf{O}}_{\bf{2}}}\)group which are arranged in different orientations. Therefore, the dimethyl fumarate total has 4 isomers.
Step 2: \(^{{\bf{13}}}{\bf{C}}\) signals
Dimethyl fumarate has different types of orientation of groups. For example, the trans orientation of groups give 3 signals in the \(^{{\rm{13}}}{\rm{C}}\) spectroscopy while in the geminal orientation of groups, the number of signals is 4.
Explanation
a.
The trans dimethyl fumarate has three signals in \(^{{\rm{13}}}{\rm{C}}\) spectroscopy as shown below:
b.
The isomers of dimethyl fumarate with signals are shown below:
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