Question

Suggest a means of demonstrating that benzylmethylphenyl-amine is not configurationally stable at room temperature.

Short answer

To demonstrate that benzylmethylphenyl-amine is not configurationally stable at room temperature, perform NMR spectroscopy on a sample of the compound dissolved in an appropriate solvent. Analyze the resultant NMR spectra for the presence of different signals corresponding to various configurations and look for exchange peaks, which indicate rapid interconversion at room temperature. If such peaks are observed, it can be concluded that benzylmethylphenyl-amine is not configurationally stable at room temperature.

Step-by-step solution

Understand the structure of benzylmethylphenyl-amine

Benzylmethylphenyl-amine has the following structure: \(CH_3-NH-C_6H_5-CH_2-C_6H_5\) This molecule contains a nitrogen atom with two different aryl groups (phenyl) attached to it, and an alkyl group (methyl). This asymmetric nitrogen atom might lead to the existence of different configurations due to its stereochemistry.

Perform NMR spectroscopy

To investigate the existence of different configurations, we can use NMR (Nuclear Magnetic Resonance) spectroscopy. This technique will provide us information about the molecular structure and the presence of various configurations. In order to perform this technique, we will need to prepare a sample of benzylmethylphenyl-amine dissolved in an appropriate NMR solvent.

Analyze NMR spectra

After obtaining the NMR spectra of the sample, carefully analyze the spectral data and look for the presence of different signals corresponding to the proton and carbon atoms of the molecule. Since the molecule is asymmetric, we might expect signals corresponding to different configurations of the molecule in the NMR spectra.

Look for exchange peaks

If benzylmethylphenyl-amine is not configurationally stable at room temperature, then we should observe exchange peaks in the NMR spectra. These exchange peaks occur due to the rapid interconversion of various configurations at room temperature. The presence of exchange peaks will indicate that the molecule is not configurationally stable at room temperature.

Conclusion

Based on the analysis of the NMR spectra, we can conclude whether benzylmethylphenyl-amine is configurationally stable or not at room temperature. If we find evidence of rapid interconversion (exchange peaks) in the NMR spectra, then we can deduce that the molecule is not configurationally stable at room temperature.

Key concepts

Benzylmethylphenylamine

Benzylmethylphenylamine is an intriguing organic compound due to its unique molecular structure. It consists of a nitrogen atom connected to one methyl group and two aryl groups, specifically phenyl groups. This trivalent configuration around the nitrogen gives rise to the possibility of different spatial arrangements—known as stereochemistry—because of the asymmetry introduced by the attached groups. Due to these structural nuances, benzylmethylphenylamine becomes a suitable candidate for studying configurational stability.
Understanding the movement or flexibility of such molecules at different temperatures is crucial in chemistry. Configurational stability refers to the persistence of a particular spatial arrangement without interconversion. For benzylmethylphenylamine, investigating if these potential configurations are stable or if they interconvert—likely at room temperature—is essential. This helps chemists understand how changes in its environment might influence its properties and reactions.

NMR Spectroscopy

NMR Spectroscopy is a fundamental analytical technique in chemistry that allows scientists to deduce the structure and dynamics of organic compounds. It works by applying a magnetic field to an atomic nucleus, resulting in the absorption of radiofrequency radiation, thus creating a unique signal known as the NMR spectrum.
For benzylmethylphenylamine, NMR spectroscopy is instrumental in identifying its structural details and detecting the presence of different configurations. When this compound is analyzed, it provides detailed information about proton ( ^{1}H NMR) and carbon ( ^{13}C NMR) environments.
This technique is precise in diagnosing whether there's a variety in molecular arrangements, as shifts and signals in the spectra directly relate to specific atoms and thus their arrangement. If benzylmethylphenylamine were to show distinct signals for each configuration, this would indicate stereochemical variation at the molecular level.

Stereochemistry

Stereochemistry refers to the three-dimensional arrangement of atoms within molecules. In benzylmethylphenylamine, it specifically addresses how the asymmetric arrangement around the nitrogen atom can result in different isomers or spatial arrangements.
The asymmetry resulting from the nitrogen being bonded to various groups can lead to chiral molecules if there's no plane of symmetry. Such asymmetry in stereochemistry is crucial for understanding the compound's behavior, especially its potential to exist in multiple forms.

• The presence of different configurations can affect a molecule's physical and chemical properties.
• Studying these aspects help chemists predict reactivity and interactions with other molecules.

In applications, recognizing and analyzing how stereochemistry affects benzylmethylphenylamine provides insights into broader chemical principles and mechanisms.

Exchange Peaks

Exchange peaks in NMR spectrums are critical indicators of dynamic processes happening within a molecule. When benzylmethylphenylamine's configurations are not stable and rapidly interchange, these peaks manifest as broadened or shifted signals in the NMR data.
These peaks are an indication that molecules are experiencing a form of dynamic equilibrium between different isomers. The energy required and the speed at which this occurs can be deduced from the type and intensity of these exchange peaks.

• Rapid interconversion at a measurable rate will produce exchange peaks.
• Presence of these peaks suggests an absence of rigidity in the molecular structure at that particular temperature.
• In benzylmethylphenylamine, observing exchange peaks would imply that configurational stability is compromised at room temperature.

This dynamic behavior is crucial not only for theoretical studies but also for practical applications where stability and consistency of a compound's configuration are necessary.