Structure using Proton NMR Spectrum

In summary, the conversation discusses the process of determining the skeletal structure of a compound with the molecular formula C3H4Cl4, based on its proton NMR spectrum. The spectrum contains two sets of triplets, one down-field and one up-field, with a relative integration ratio of 2:2. The experts suggest that the molecule must be symmetrical, and after considering the complexity of splitting and integration ratios, the correct structure is determined to be Cl2-CH-CH2-CH-Cl2. The initial solution proposed by the speaker, Cl3C-CH2-CH2-Cl, also produces the same spectrum but is not considered correct due to the possibility of a complex splitting for the central methylene.
  • #1
GoldDelight
4
0

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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  • #2
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?
 
  • #3
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.
 

Related to Structure using Proton NMR Spectrum

What is a proton NMR spectrum?

A proton NMR (Nuclear Magnetic Resonance) spectrum is a type of analytical technique used to determine the structure of a molecule. It involves measuring the energy absorbed by the nuclei of hydrogen atoms in a molecule when placed in a strong magnetic field.

How does a proton NMR spectrum work?

A proton NMR spectrum works by exposing a sample of a compound to a strong magnetic field, which causes the nuclei of hydrogen atoms to align either with or against the field. Then, a pulse of radiofrequency radiation is applied, causing the hydrogen nuclei to flip back and forth between the two alignments. This flip-flopping results in an energy difference that can be detected and used to create a spectrum.

What information can be obtained from a proton NMR spectrum?

A proton NMR spectrum can provide information about the number of hydrogen atoms in a molecule, the types of hydrogen environments they are in (based on their chemical shift), and the connectivity between different hydrogen atoms. This information can help determine the structure of the molecule.

What does the chemical shift in a proton NMR spectrum indicate?

The chemical shift in a proton NMR spectrum indicates the electronic environment of a hydrogen atom. It is measured in parts per million (ppm) and is affected by factors such as the electronegativity of nearby atoms and the hybridization state of the carbon atom to which the hydrogen is bonded.

Can a proton NMR spectrum be used to determine the exact structure of a molecule?

While a proton NMR spectrum can provide valuable information about a molecule's structure, it is not always enough to determine the exact structure. Other analytical techniques, such as carbon NMR and mass spectrometry, may also be necessary to fully determine the structure of a molecule.

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