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Treatment of benzaldehyde \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}\right)\) with \(\mathrm{Zn}(\mathrm{Hg})\) in aqueous \(\mathrm{HCl}\) forms a compound \(\mathrm{Z}\) that has a molecular ion at 92 in its mass spectrum. \(Z\) shows absorptions at \(3150-2950,1605\), and \(1496 \mathrm{~cm}^{-1}\) in its IR spectrum. Give a possible structure for \(Z\).

Short Answer

Expert verified
Compound Z is toluene (C鈧咹鈧匔H鈧).

Step by step solution

01

Understanding the Reaction

Benzaldehyde (C鈧咹鈧匔HO) is undergoing a Clemensen reduction, where Zn(Hg) in aqueous HCl converts the aldehyde group (CHO) into a corresponding alkyl group (CH鈧). This transformation is typical when using this set of reagents, which are known for reducing carbonyl groups to hydrocarbons.
02

Analyze the Molecular Ion Peak

The molecular ion peak at 92 suggests that the molecular weight of compound Z is 92. Since benzaldehyde has a molecular weight of 106 u, and the reduction removes the oxygen atom from the carbonyl group (C=O), resulting in C鈧咹鈧匔H鈧 (toluene), whose molecular weight is 92.
03

Analyze the IR Absorption Bands

The IR absorption bands provide insight into the functional groups present: - The strong absorption between 3150-2950 cm鈦宦 indicates the presence of C-H stretching in an aromatic ring. - The absorption at 1605 cm鈦宦 is typical for C=C stretching in an aromatic ring. - The absorption at 1496 cm鈦宦 is another indication of C=C stretching in an aromatic system. These peaks are consistent with the presence of an aromatic benzene ring, further confirming the structure of toluene.
04

Proposing Structure of Compound Z

Based on the reaction type, molecular weight, and IR data, compound Z is identified as toluene (C鈧咹鈧匔H鈧). The reduction of the carbonyl group in benzaldehyde and presence of aromatic ring characteristics in the IR spectrum support this proposed structure.

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Key Concepts

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

Benzaldehyde
Benzaldehyde, with the formula \( \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO} \), is a fundamental aromatic aldehyde often used as a starting material in organic synthesis. It has a distinctive almond-like smell. This compound is characterized by a benzene ring (\(\mathrm{C}_{6}\mathrm{H}_{5}\)) connected to a carbonyl group \((\mathrm{CHO}\)). Importantly, the carbonyl group (\( \mathrm{C}=\mathrm{O} \)) is largely responsible for benzaldehyde's reactivity. This specific part of the molecule can undergo various types of chemical reactions, like reductions, transformations that are pivotal in organic chemistry.
In the context of the Clemensen reduction, benzaldehyde is the starting material that undergoes conversion to an alkylbenzene by replacing the carbonyl with an alkyl group \((\mathrm{CH}_3)\). The conversion is possible by using reagents such as zinc amalgam (\(\mathrm{Zn(Hg)}\)) and hydrochloric acid \((\mathrm{HCl})\). This powerful reaction highlights the versatility of benzaldehyde derivatives in producing diverse aromatic compounds.
Mass Spectrometry
Mass spectrometry is a valuable analytical technique used for determining the molecular weight of compounds by ionizing chemical species and sorting the ions based on their mass-to-charge ratio. When benzaldehyde is reduced to compound \( Z \), the mass spectrum reveals a molecular ion peak at 92. This peak is crucial as it indicates the molecular weight of \( Z \).
The peak at 92 corresponds to the mass of toluene \(( \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{3} )\), which aligns with the expected result of the Clemensen reduction procedure. The presence of this mass suggests the removal of the oxygen from benzaldehyde, leaving behind a simple hydrocarbon with a total mass that equals 92 atomic mass units. Mass spectrometry thus provides a quick verification tool for observing the molecular transformations occurring during chemical reactions.
IR Spectroscopy
Infrared (IR) spectroscopy is an essential tool in structural elucidation because it identifies functional groups based on their vibrational transitions. In the case of compound \( Z \), the IR spectrum shows several characteristic absorption bands:
  • The 3150-2950 cm鈦宦 region showing strong absorption is commonly associated with C-H stretching vibrations in an aromatic ring.
  • Band at 1605 cm鈦宦 corresponds to C=C stretching typical of aromatic systems.
  • Another band at 1496 cm鈦宦 further supports the presence of C=C stretching in the aromatic ring.

These absorption bands collectively confirm the presence of the benzene ring in compound \( Z \). The IR spectrum thus complements mass spectrometry by verifying the structural retention of the aromatic core present in the original benzaldehyde.
Structural Determination
Structural determination is a process combining data from multiple analytical techniques to construct the most probable structure of a compound. In the exercise with compound \( Z \), our objective is to propose a structure by interpreting evidence from both mass spectrometry and IR spectroscopy.
The mass spectrometry result suggesting a molecular ion peak at 92, combined with IR spectroscopy data indicating characteristic aromatic ring vibrations, strongly suggests that compound \( Z \) is toluene \((\mathrm{C}_{6}\mathrm{H}_{5}\mathrm{CH}_3)\). This process embodies the usage ofdiverse analytical approaches to deduce the final chemical architecture. Such analyses ensure accuracy in identifying compounds resulting from complex reactions, a critical skill set in organic chemistry.

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Most popular questions from this chapter

How do the IR spectra of the isomers cyclopentane and 1 -pentene differ?

Propose possible structures consistent with each set of data. Assume each compound has an \(s p^{3}\) hybridized \(\mathrm{C}-\mathrm{H}\) absorption in its IR spectrum, and that other major IR absorptions above \(1500 \mathrm{~cm}^{-1}\) are listed. a. A compound having a molecular ion at 72 and an absorption in its IR spectrum at \(1725 \mathrm{~cm}^{-1}\) b. A compound having a molecular ion at 55 and an absorption in its IR spectrum at \(-2250 \mathrm{~cm}^{-1}\) c. A compound having a molecular ion of 74 and an absorption in its IR spectrum at \(3600-3200 \mathrm{~cm}^{-1}\)

Which of the following has the higher energy: (a) light having a v of \(10^{4} \mathrm{~Hz}\) or \(10^{8} \mathrm{~Hz} ;\) (b) light having a \(\lambda\) of \(10 \mathrm{~nm}\) or \(1000 \mathrm{~nm} ;(\mathrm{c})\) red light or blue light?

Benzene, toluene, and \(p\) -xylene (BTX) are often added to gasoline to boost octane ratings. What would be observed if a mixture of these three compounds were subjected to GC-MS analysis? How many peaks would be present in the gas chromatogram? What would be the relative order of the peaks? What molecular ions would be observed in the mass spectra?

Reaction of pentanoyl chloride \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COCl}\right)\) with lithium dimethyl cuprate \(\left[\mathrm{LiCu}\left(\mathrm{CH}_{3}\right)_{2}\right]\) forms a compound \(\mathrm{J}\) that has a molecular ion in its mass spectrum at 100 , as well as fragments at \(m / z=85,57\), and 43 (base). The IR spectrum of \(\mathrm{J}\) has strong peaks at 2962 and \(1718 \mathrm{~cm}^{-1}\). Propose a structure for \(\mathbf{J}\).

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