a. How many signals does dimethyl fumarate (CH3O2CCH = CHCO2CH3, with a trans C = C) exhibit in its 13C NMR spectrum?b. Draw the structure of an isomer of dimethyl fumarate that has each of the following number of signals in its 13C NMR spectrum: [1] three; [2] four; [5] five.

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Asked Dec 29, 2019
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a. How many signals does dimethyl fumarate (CH3O2CCH = CHCO2CH3, with a trans C = C) exhibit in its 13C NMR spectrum?
b. Draw the structure of an isomer of dimethyl fumarate that has each of the following number of signals in its 13C NMR spectrum: [1] three; [2] four; [5] five.

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Expert Answer

Step 1

a. Dimethyl fumarate contains two methyl groups. The carbon-carbon double bond has trans configuration. It has a center of symmetry. There are three chemically non-equivalent carbon

atoms present in dimethyl fumarate. Therefore, it gives three signals in 13C NMR spectrum.

Chemistry homework question answer, step 1, image 1
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Step 2

b. An isomer of dimethyl fumarate with molecular formula C6H8O4 must have different stereochemistry at carbon-carbon double bond. The cis isomer of dimethyl fumarate has two hydrogen atoms in the same face of double bond. It has a plane of symmetry. There are three chemically non-equivalent carbon atoms. Therefore, it gives three signals in 13C NMR spectrum. The structure of dimethyl fumarate in cis configuration with three signals is shown below.

Chemistry homework question answer, step 2, image 1
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Step 3

The structure shown below is 3-methylenepentanedioic acid, an isomer of dimethyl fumarate. It has four c...

Chemistry homework question answer, step 3, image 1
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