Structure using Proton NMR Spectrum

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SUMMARY

The discussion centers on determining the skeletal structure of the compound with the molecular formula C3H4Cl4 based on its proton NMR spectrum, which features a down-field triplet and an up-field triplet with a relative integration of 2:2. The correct structure is identified as Cl2-CH-CH2-CH-Cl2, indicating a symmetrical arrangement of chlorinated carbons. The initial proposed structure, Cl3C-CH2-CH2-Cl, was incorrect due to the complexity of splitting patterns expected from the chlorinated positions. The integration ratios and symmetry of the molecule are critical in deducing the correct structure.

PREREQUISITES
  • Understanding of proton NMR spectroscopy and integration ratios
  • Knowledge of molecular symmetry and its implications in NMR analysis
  • Familiarity with chlorinated hydrocarbons and their structural representations
  • Basic skills in drawing skeletal structures of organic compounds
NEXT STEPS
  • Study the principles of proton NMR spectroscopy, focusing on integration and splitting patterns
  • Learn about molecular symmetry and its effects on NMR spectra interpretation
  • Research chlorinated hydrocarbons and their common structural features
  • Practice drawing skeletal structures for various organic compounds with different functional groups
USEFUL FOR

Chemistry students, organic chemists, and anyone involved in structural analysis using NMR spectroscopy will benefit from this discussion.

GoldDelight
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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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