Structure using Proton NMR Spectrum

AI Thread Summary
The discussion revolves around determining the skeletal structure of a compound with the molecular formula C3H4Cl4 based on its proton NMR spectrum, which shows two triplets with a 2:2 integration ratio. The integration suggests the presence of two CH2 groups, leading to the conclusion that one carbon must have three chlorine atoms attached. A proposed structure, Cl3C-CH2-CH2-Cl, was deemed incorrect due to the symmetry required for the observed NMR pattern. The correct structure identified is Cl2-CH-CH2-CH-Cl2, which aligns with the expected splitting and integration ratios. The complexity of the NMR interpretation highlights the challenges in accurately deducing molecular structures from spectral data.
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Homework Statement


Draw the skeletal structure of the compound with molecular formulaC3H4Cl4 whose proton NMR spectrum contains a down-field triplet and an up-field triplet with relative integration of 2:2.
2. Rationale for Solution
Integration ratio of 2:2 means CH2-CH2, after this one carbon and 4 Cl left. One carbon must have 3 Cl and the last chlorine must be attached to one of the CH2 to complete C octet

The Attempt at a Solution


My solution for this is Cl3C-CH2-CH2-Cl but it is being marked wrong. I don't know why.
 
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Since there are only two groups of triplets, the molecule must be symmetrical. Otherwise, there would be two triplets for the Cl3 substituted and the Cl substituted carbons. In your case, the central methylene would have a complex splitting... something like a triplet split in two, right? And the protons attached to the chlorinated positions would integrate to 1:3 as well, yes?
 
Well, it turned out to be Cl2-CH-CH2-CH-Cl2. It was trickier than what I thought. But I have to say the my first solution also produces same spectrum and, in my mind based on the information given, there is no way to decide between the two.
 
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