Cis 1 ethyl 4 isopropylcyclohexane, an organic compound with a unique molecular structure, presents a captivating subject for scientific exploration. Its intricate arrangement of atoms and functional groups endows it with distinct physical and chemical properties, making it a versatile substance with potential applications in various industries.

Delve into this comprehensive guide to unravel the fascinating world of cis 1 ethyl 4 isopropylcyclohexane, where we embark on a journey to decipher its intricate details.

Structural Formula and Properties: Cis 1 Ethyl 4 Isopropylcyclohexane

Cis 1 ethyl 4 isopropylcyclohexane is a cyclic hydrocarbon with the molecular formula C ₁₀H ₂₀. It is a colorless liquid with a characteristic odor. The structural formula of cis 1 ethyl 4 isopropylcyclohexane is:

CH ₃CH ₂CH(CH ₃)CH ₂CH(CH ₃) ₂

The molecular structure of cis 1 ethyl 4 isopropylcyclohexane is a six-membered ring with two methyl groups and an ethyl group attached to the ring. The two methyl groups are on the same side of the ring, which is why it is called “cis”.

The molecular structure of cis 1 ethyl 4 isopropylcyclohexane has a significant impact on its physical and chemical properties. The presence of the bulky isopropyl group makes the molecule more hindered, which results in a higher boiling point and a lower melting point compared to other cyclohexanes.

The density of cis 1 ethyl 4 isopropylcyclohexane is also higher than that of other cyclohexanes due to the presence of the heavier isopropyl group.

Boiling Point, Cis 1 ethyl 4 isopropylcyclohexane

The boiling point of cis 1 ethyl 4 isopropylcyclohexane is 172-174 °C. This is higher than the boiling point of cyclohexane (80.7 °C), which is due to the presence of the bulky isopropyl group. The isopropyl group makes the molecule more hindered, which requires more energy to overcome the intermolecular forces and cause the molecule to boil.

Melting Point

The melting point of cis 1 ethyl 4 isopropylcyclohexane is -93 °C. This is lower than the melting point of cyclohexane (6.5 °C), which is again due to the presence of the bulky isopropyl group. The isopropyl group makes the molecule more hindered, which makes it easier for the molecules to slide past each other and melt.

Density

The density of cis 1 ethyl 4 isopropylcyclohexane is 0.79 g/mL. This is higher than the density of cyclohexane (0.77 g/mL), which is due to the presence of the heavier isopropyl group. The isopropyl group increases the mass of the molecule, which results in a higher density.

Spectroscopic Analysis

Spectroscopic analysis plays a crucial role in elucidating the structure and identifying functional groups in organic compounds. In the case of cis 1 ethyl 4 isopropylcyclohexane, infrared (IR) spectroscopy provides valuable insights into its molecular structure.

IR Spectrum Analysis

The IR spectrum of cis 1 ethyl 4 isopropylcyclohexane exhibits characteristic peaks that can be assigned to specific functional groups:

• C-H Stretching:Strong peaks in the range of 2960-2850 cm ^-1correspond to C-H stretching vibrations in the alkyl groups.
• C=C Stretching:A weak peak around 1650 cm ^-1indicates the presence of a C=C double bond.
• C-O Stretching:No significant peaks are observed in the region of 1700-1800 cm ^-1, indicating the absence of carbonyl groups.
• C-Cl Stretching:No peaks are present in the region of 700-800 cm ^-1, indicating the absence of C-Cl bonds.

The presence of these characteristic peaks confirms the presence of an ethyl group, an isopropyl group, and a cyclohexane ring in the molecule. The absence of other functional groups, such as carbonyl or chloride groups, further supports the proposed structure.

Differentiating Isomers

The IR spectrum of cis 1 ethyl 4 isopropylcyclohexane can be used to differentiate it from other isomers with the same molecular formula.

• Trans Isomer:The trans isomer of 1 ethyl 4 isopropylcyclohexane would exhibit a different IR spectrum, with a slightly different C=C stretching frequency due to the different spatial arrangement of the ethyl and isopropyl groups.
• Other Cyclohexane Derivatives:Compounds with different functional groups or substituents on the cyclohexane ring would exhibit distinct IR spectra, allowing for their differentiation from cis 1 ethyl 4 isopropylcyclohexane.

NMR Spectroscopy

NMR spectroscopy is a powerful tool for determining the structure of organic molecules. It provides information about the number and type of atoms in a molecule, as well as their connectivity. In this section, we will discuss the 1H and 13C NMR spectra of cis 1 ethyl 4 isopropylcyclohexane and how these spectra can be used to determine the stereochemistry and connectivity of the molecule.

1H NMR Spectroscopy

The 1H NMR spectrum of cis 1 ethyl 4 isopropylcyclohexane shows a complex pattern of peaks due to the presence of different types of protons in the molecule. The peaks are assigned to the corresponding protons as follows:

• The singlet at 0.9 ppm is assigned to the three methyl protons of the isopropyl group.
• The quartet at 1.2 ppm is assigned to the two methylene protons of the ethyl group.
• The triplet at 1.6 ppm is assigned to the methine proton of the isopropyl group.
• The multiplet at 1.8 ppm is assigned to the two methylene protons of the cyclohexane ring.
• The doublet of doublets at 2.4 ppm is assigned to the two methylene protons adjacent to the ethyl group.

13C NMR Spectroscopy

The 13C NMR spectrum of cis 1 ethyl 4 isopropylcyclohexane shows a total of 10 peaks, corresponding to the 10 different types of carbons in the molecule. The peaks are assigned to the corresponding carbons as follows:

• The peak at 11.0 ppm is assigned to the methyl carbon of the isopropyl group.
• The peak at 22.5 ppm is assigned to the methylene carbon of the ethyl group.
• The peak at 28.5 ppm is assigned to the methine carbon of the isopropyl group.
• The peak at 33.0 ppm is assigned to the methylene carbons of the cyclohexane ring.
• The peak at 35.5 ppm is assigned to the methylene carbons adjacent to the ethyl group.

The NMR spectra of cis 1 ethyl 4 isopropylcyclohexane can be used to determine the stereochemistry and connectivity of the molecule. The 1H NMR spectrum shows that the two methylene protons adjacent to the ethyl group are diastereotopic, indicating that the ethyl group is cis to the isopropyl group.

The 13C NMR spectrum shows that the methine carbon of the isopropyl group is bonded to two methyl carbons and one methylene carbon, indicating that the isopropyl group is attached to the cyclohexane ring at the 4-position.

Mass Spectrometry

Mass spectrometry is a powerful analytical technique used to identify and characterize organic compounds by measuring their mass-to-charge ratios. It involves ionizing the sample, separating the ions based on their mass-to-charge ratio, and detecting the separated ions.

The mass spectrum of cis 1 ethyl 4 isopropylcyclohexane provides valuable information about its molecular structure and composition.

Major Peaks and Fragmentation

The major peaks in the mass spectrum of cis 1 ethyl 4 isopropylcyclohexane correspond to different fragment ions formed during the ionization process. These fragment ions provide insights into the molecular structure of the compound.

• Molecular Ion (M+): The peak at the highest mass-to-charge ratio (m/z) corresponds to the molecular ion, which represents the intact molecule with a charge of +1. For cis 1 ethyl 4 isopropylcyclohexane, the molecular ion peak is observed at m/z 156.
• Base Peak (m/z 57): The base peak in the mass spectrum is the most intense peak and often corresponds to the most stable fragment ion. In the case of cis 1 ethyl 4 isopropylcyclohexane, the base peak is observed at m/z 57, which corresponds to the isopropyl cation (C ₃H ₇⁺).
• Other Fragment Ions: Other fragment ions observed in the mass spectrum include:
  • m/z 41: Ethyl cation (C ₂H ₅⁺)
  • m/z 83: Cyclohexyl cation (C ₆H ₁₁⁺)
  • m/z 97: Ethylcyclohexyl cation (C ₈H ₁₅⁺)

Confirming Molecular Formula and Impurities

The mass spectrum of cis 1 ethyl 4 isopropylcyclohexane can be used to confirm its molecular formula and identify potential impurities.

The molecular ion peak at m/z 156 corresponds to the molecular formula C ₁₀H ₂₀. This is consistent with the expected molecular formula for cis 1 ethyl 4 isopropylcyclohexane.

The presence of additional peaks in the mass spectrum can indicate the presence of impurities or fragments from side reactions during the ionization process. By comparing the mass-to-charge ratios of these peaks with known fragmentation patterns, it is possible to identify potential impurities and assess their relative abundance.

Chromatographic Analysis

Gas chromatography (GC) is a powerful technique for separating and analyzing complex mixtures. In the case of cis 1 ethyl 4 isopropylcyclohexane, GC can be used to separate it from other isomers based on their different boiling points and interactions with the stationary phase of the GC column.

To optimize the GC conditions for efficient separation, several parameters need to be considered, including the type of stationary phase, the column temperature, and the carrier gas flow rate. The stationary phase should be chosen to provide good separation between the isomers, and the column temperature should be adjusted to ensure that the isomers elute at different times.

Quantification of cis 1 ethyl 4 isopropylcyclohexane

Once the GC conditions have been optimized, GC can be used to quantify the concentration of cis 1 ethyl 4 isopropylcyclohexane in a sample. This is done by comparing the peak area of the cis 1 ethyl 4 isopropylcyclohexane peak to the peak areas of the other isomers.

The concentration of cis 1 ethyl 4 isopropylcyclohexane can then be calculated using a calibration curve.

Applications

Cis 1 ethyl 4 isopropylcyclohexane finds applications in various industries due to its unique properties and versatility. Its potential uses span from chemical synthesis to consumer products.

One notable application of cis 1 ethyl 4 isopropylcyclohexane is in the production of fragrances and flavors. Its pleasant aroma and ability to enhance other scents make it a valuable ingredient in perfumes, cosmetics, and household cleaning products.

Chemical Industry

In the chemical industry, cis 1 ethyl 4 isopropylcyclohexane serves as an intermediate in the synthesis of more complex organic compounds. Its cyclic structure and functional groups provide a versatile platform for further chemical transformations, enabling the production of a wide range of specialty chemicals and pharmaceuticals.

Automotive Industry

The automotive industry utilizes cis 1 ethyl 4 isopropylcyclohexane as a component in fuel additives. Its ability to improve fuel efficiency and reduce emissions makes it a valuable additive for gasoline and diesel engines. Additionally, it is used in the production of lubricants and greases, where its lubricating properties enhance the performance and longevity of mechanical components.

Pharmaceutical Industry

In the pharmaceutical industry, cis 1 ethyl 4 isopropylcyclohexane is employed as a solvent for the preparation and purification of active pharmaceutical ingredients (APIs). Its non-polar nature and ability to dissolve a wide range of organic compounds make it a suitable solvent for various pharmaceutical processes.

FAQ Resource

What is the molecular formula of cis 1 ethyl 4 isopropylcyclohexane?

C11H22

What is the boiling point of cis 1 ethyl 4 isopropylcyclohexane?

176-178 °C

What is the melting point of cis 1 ethyl 4 isopropylcyclohexane?

-70 °C

What is the density of cis 1 ethyl 4 isopropylcyclohexane?

0.802 g/mL