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Chlorooctanes

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Identification
Molecular formula
C8H17Cl
CAS number
5402-88-8; 1077-14-7; 5326-35-8
IUPAC name
2-chlorooctane;3-chlorooctane;4-chlorooctane
State
State

Liquid: At room temperature, chlorooctanes are in a liquid state. These compounds are typically used in chemical syntheses and may also be found as intermediates in various industrial processes.

Melting point (Celsius)
-68.00
Melting point (Kelvin)
205.15
Boiling point (Celsius)
184.00
Boiling point (Kelvin)
457.15
General information
Molecular weight
148.64g/mol
Molar mass
148.6420g/mol
Density
0.8441g/cm3
Appearence

Chlorooctanes, in general, are clear, colorless to pale yellow liquids. They may appear slightly viscous depending on the isomer and can have an oily texture. They are typically transparent and may have a faint, sweetish odor characteristic of chlorinated hydrocarbons.

Comment on solubility

Solubility of 2-chlorooctane, 3-chlorooctane, and 4-chlorooctane

The solubility of chlorinated compounds such as 2-chlorooctane, 3-chlorooctane, and 4-chlorooctane can vary significantly based on their molecular structure and the nature of the chlorination. Generally, the solubility characteristics of these compounds are influenced by:

  • Hydrophobic Interactions: The long hydrocarbon chain tends to impart hydrophobic properties, making these compounds less soluble in water.
  • Chlorine Atoms: The presence of chlorine, a highly electronegative atom, introduces polarity, which can enhance solubility in polar solvents, but may reduce it in non-polar solvents.
  • Branching Effects: The position of the chlorine atom (as in 2-, 3-, or 4-chlorooctane) can affect steric hindrance and therefore influence solubility in various solvents.

In general, these chlorinated octanes are more soluble in organic solvents such as hexane or acetone than in water. Their solubility in specific solvents can be summarized as follows:

  1. 2-chlorooctane: Moderate solubility in organic solvents; low solubility in water.
  2. 3-chlorooctane: Similar properties to 2-chlorooctane but may exhibit slight variations due to chlorine position affecting intermolecular interactions.
  3. 4-chlorooctane: Generally shows the same solubility pattern as the others, though structural differences can play a role in the exact solubility profile.

In conclusion, while these compounds are primarily insoluble in water, they can dissolve well in organic solvents, showcasing a classic example of the principle that "like dissolves like."

Interesting facts

Interesting Facts about 2-Chlorooctane, 3-Chlorooctane, and 4-Chlorooctane

The compounds 2-chlorooctane, 3-chlorooctane, and 4-chlorooctane are all members of the alkyl halide family, showcasing the fascinating chemistry associated with haloalkanes. Understanding the variations in chlorine positioning within these octane derivatives provides insight into their chemical behavior and applications.

Key Properties and Applications

  • Structure-Activity Relationship: The placement of the chlorine atom on different carbon atoms influences the physical properties and reactivity of each compound. For example, the reactivity in nucleophilic substitution reactions can vary significantly.
  • Solvent Applications: These chlorinated octanes are utilized as solvents in chemical reactions due to their ability to dissolve a variety of organic compounds, making them valuable in both laboratory and industrial settings.
  • Precursor to Synthesis: They serve as intermediates in the synthesis of more complex organic compounds, enabling chemists to create a range of useful chemicals, including pharmaceuticals and agrochemicals.
  • Environmental Considerations: The chlorine content in these compounds raises concerns regarding environmental impact. Researchers are actively studying alternatives that can reduce environmental footprints.

Chemical Behavior

Each isomer presents unique characteristics:

  • 2-Chlorooctane: Often favored for its properties in radical reactions due to the stability afforded by its position, it shows distinct reactivity patterns compared to its isomers.
  • 3-Chlorooctane: This isomer may exhibit diverse reactions based on steric hindrance, influencing how it reacts with nucleophiles.
  • 4-Chlorooctane: Known for its increased steric effects, making reactions more selective and providing interesting outcomes in synthesis.

A quote from renowned chemist Linus Pauling resonates strongly with the study of these compounds: "The best way to have a good idea is to have a lot of ideas." Indeed, the variations in structure lead to a myriad of applications and potential discoveries.

In summary, the study of 2-chlorooctane, 3-chlorooctane, and 4-chlorooctane exemplifies the richness of organic chemistry, where minor structural changes lead to significant differences in chemical behavior and utility. Each compound not only has its applications but also reminds us of the ongoing need for environmentally conscious chemistry.

Synonyms
26655-49-2
SCHEMBL230466
2-chlorooctane;3-chlorooctane;4-chlorooctane