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I know the answer is the last picture, but can someone tell me why? I understand

ID: 810293 • Letter: I

Question

I know the answer is the last picture, but can someone tell me why? I understand that the aromatic ring comes from the multiplet that integrates to 5 atoms, but I don't understand the rest. Since it tells us there are 2 singlets (which means that there are 2 carbons w/ 0 Hydrogen atoms on the carbons next to it, right?), but picture 1 and picture 3 both have that feature.

A compound has the formula C10H13Cl. Its 1H NMR spectrum consists of a singlet at 1.6 ppm, a singlet at 3.1 ppm, and a multiplet at 7.2 ppm that integrates to 5 hydrogen atoms. The most likely structure for the compound is: I know the answer is the last picture, but can someone tell me why? I understand that the aromatic ring comes from the multiplet that integrates to 5 atoms, but I don't understand the rest. Since it tells us there are 2 singlets (which means that there are 2 carbons w/ 0 Hydrogen atoms on the carbons next to it, right?), but picture 1 and picture 3 both have that feature.

Explanation / Answer

In the third structure there are two protons containing carbon in between the carbon atoms without hydrogen that is RCH2R the region is around 1.2 to 1.7. this feature is not there in structure 1