Draw all constitutional isomers of molecular formula C3H6Cl2.a. How many signals does each isomer exhibit in its 1H NMR spectrum?b. How many lines does each isomer exhibit in its 13C NMR spectrum?c. When only the number of signals in both 1H and 13C NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?

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Asked Dec 29, 2019
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Draw all constitutional isomers of molecular formula C3H6Cl2.
a. How many signals does each isomer exhibit in its 1H NMR spectrum?
b. How many lines does each isomer exhibit in its 13C NMR spectrum?
c. When only the number of signals in both 1H and 13C NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?

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Expert Answer

Step 1

a. The isomers 1,1- dichloropropane and 1, 2- dichloropropane has three non-equivalent protons. Therefore, they given three signals in their IH — NMR spectra. The isomer 1, 3-dichloropropane shows two types of chemically non-equivalent protons in its structure. Therefore, it gives two signals in 1H-NMR spectrum. Similarly, the isomer 2,2-dichloropropane shows two types of chemically non-equivalent protons in its structure. Therefore, it gives two signals in 1H -NMR spectrum.

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

b. In the 13C NMR spectrum, the number oflines in each compound is equal to the number of carbon atoms present in a different chemical environment.

The isomers 1,1-dichloropropane and 1, 2-dichloropropane has three non-equivalent carbon atoms. Therefore, they give three lines in their 13C-NMR spectra.

The isomer 1, 3- dichloropropane shows two ...

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