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A certain halogen compound gave a mass spectrum with molecular ion peaks at \(m / e 136\) and 138 in about equal intensities. The nmr spectrum of this compound gave only a single resonance around \(1.2 \mathrm{ppm}\). What is the structure of the compound? Give your reasoning.

Short Answer

Expert verified
The compound is tert-butyl chloride, \(\mathrm{C}_4\mathrm{H}_9\mathrm{Cl}\).

Step by step solution

01

Analyze the Mass Spectrum Peaks

The mass spectrum shows peaks at \(m/e 136\) and \(138\) with equal intensities. This suggests the presence of two isotopes that differ by 2 amu (atomic mass units), typically found in the presence of chlorine, where \(^{35}\mathrm{Cl}\) and \(^{37}\mathrm{Cl}\) isotopes are present in almost equal ratios.
02

Identify the Potential Halogen Compound

Since the compound shows two peaks with similar intensities due to chlorine isotopes, it suggests the presence of a monochloride. Thus, the compound could be a chloride of some hydrocarbon.
03

Consider the NMR Spectrum

The NMR spectrum shows a single resonance at \(1.2 \mathrm{ppm}\). This indicates that all hydrogen atoms are in an equivalent environment, which is typical of a symmetrical structure or a molecule with no other structural features affecting the hydrogen resonance.
04

Deduce the Structure of the Compound

Given the single peak in the NMR spectrum and the mass spectrum data, the compound is likely tert-butyl chloride \((\mathrm{C}_4\mathrm{H}_9\mathrm{Cl})\). The molar mass fits with the observed masses \(m/e 136\) and \(138\) (90 amu from \(\mathrm{C}_4\mathrm{H}_9\) and 35 or 37 amu from \(\mathrm{Cl}\)) and all the hydrogens in \(\mathrm{C}_4\mathrm{H}_9\) are equivalent, showing a single resonance.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Nuclear Magnetic Resonance (NMR)
Nuclear Magnetic Resonance (NMR) is a powerful analytical technique used to observe the local magnetic fields around atomic nuclei. This method provides information about the structure, dynamics, reaction state, and chemical environment of molecules. At its core, NMR exploits the magnetic properties of certain atomic nuclei. When placed in a magnetic field, nuclei of atoms resonate at a specific frequency. Bombarding them with radio frequency radiation causes a transition to a higher energy state. When they return to their lower energy state, they emit a signal that can be detected and translated into a spectrum. In an NMR spectrum, the position of resonance peaks, usually measured in parts per million (ppm), offers insight into the chemical environment of the nuclei. For example, a single resonance around 1.2 ppm, as seen in this exercise, suggests that all hydrogen atoms are in an identical environment. This indicates a simple, symmetrical structure without complex substituents or functional groups, offering clues about the compound's identity.
Isotopic Abundance
Isotopic abundance refers to the relative amount of different isotopes of an element found in a sample. Isotopes are naturally occurring variations of elements that have the same number of protons but different numbers of neutrons, leading to differences in their atomic masses.In the context of mass spectrometry, isotopic abundance is crucial for interpreting spectra. In this exercise, where we have peaks at 136 and 138 m/e, these correspond to two isotopes of chlorine:
  • The lighter isotope, \(^{35}\mathrm{Cl}\), gives a peak at m/e 136.
  • The heavier isotope, \(^{37}\mathrm{Cl}\), gives a peak at m/e 138.
Because chlorine isotopes occur in almost equal proportions (\(^{35}\mathrm{Cl}:^{37}\mathrm{Cl} \approx 3:1\)), we see peaks of similar intensity. This isotopic pattern often serves as a 'fingerprint,' helping confirm the presence of specific elements, like chlorine in the given compound.
Molecular Ion Peak
The molecular ion peak in a mass spectrum is the peak representing the ion formed by the removal of an electron from a molecule, thus producing a cation that reflects the molecule's original mass. In mass spectrometry, understanding molecular ion peaks helps deduce molecular weights and potential structures of compounds. This ion is crucial because its mass gives a direct indication of the possible molecular mass of the compound. In the problem at hand, the presence of molecular ion peaks at 136 and 138 m/e reflects the compound's overall mass, including isotopic variations. The peaks suggest potential molecular weights consistent with a halogen compound containing chlorine due to their distinct mass difference of 2 amu. This mass pattern helps determine the molecular formula and guides chemists in proposing logical structures, such as tert-butyl chloride. Together with NMR data, this confirms structural hypotheses, pairing molecular fragments accurately with corresponding spectral data.

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