Prepare to delve into the fascinating realm of cis 1 chloro 2 methylcyclohexane! This compound, boasting a unique molecular structure and diverse applications, is poised to captivate your curiosity.
From its physical and chemical properties to its synthesis and reactions, we’ll unravel the intricate details that define cis 1 chloro 2 methylcyclohexane, leaving no stone unturned in our quest for knowledge.
Chemical Structure
Cis 1 chloro 2 methylcyclohexane is an organic compound with the molecular formula C 7H 13Cl. It is a colorless liquid with a pungent odor. The molecule consists of a cyclohexane ring with a chlorine atom and a methyl group attached to the same carbon atom.
The IUPAC name for this compound is (1-chloromethylcyclohexyl)methane, and its common name is cis 1 chloro 2 methylcyclohexane.
Molecular Structure
The molecular structure of cis 1 chloro 2 methylcyclohexane can be represented by the following Lewis structure:
The carbon atoms in the cyclohexane ring are arranged in a chair conformation, with the chlorine atom and the methyl group both attached to the same carbon atom. The two hydrogen atoms on the carbon atom that bears the chlorine and methyl groups are in a cis configuration, meaning that they are on the same side of the ring.
Physical and Chemical Properties
Cis 1 chloro 2 methylcyclohexane exhibits distinct physical and chemical properties that influence its behavior and applications.
Physical Properties
- Boiling Point:159-161 °C
- Melting Point:-64 °C
- Density:0.98 g/cm³ at 20 °C
Chemical Properties
Cis 1 chloro 2 methylcyclohexane possesses a reactive chlorine atom that renders it susceptible to nucleophilic substitution reactions. It undergoes SN2 reactions with a wide range of nucleophiles, such as hydroxide, alkoxide, and amine anions.
The compound is relatively stable under normal conditions but can undergo elimination reactions under certain conditions, such as heating in the presence of a strong base. It exhibits weak polarity due to the electronegativity difference between carbon and chlorine, making it slightly soluble in both polar and nonpolar solvents.
Synthesis and Reactions
Cis 1-chloro-2-methylcyclohexane can be synthesized through various methods, with the most common being the addition of hydrogen chloride (HCl) to 1-methylcyclohexene. This reaction proceeds via an electrophilic addition mechanism, where the electrophilic hydrogen ion (H+) adds to the double bond of 1-methylcyclohexene, followed by the addition of the nucleophilic chloride ion (Cl-).
Reactivity
Cis 1-chloro-2-methylcyclohexane is a reactive compound due to the presence of the chlorine atom, which can undergo various reactions. These reactions include nucleophilic substitution, elimination, and addition reactions.
Nucleophilic Substitution Reactions
Cis 1-chloro-2-methylcyclohexane can undergo nucleophilic substitution reactions with a variety of nucleophiles, such as hydroxide ion (OH-), alkoxide ions (RO-), and ammonia (NH3). These reactions result in the replacement of the chlorine atom with the nucleophile, forming the corresponding alcohol, ether, or amine.
Elimination Reactions
Cis 1-chloro-2-methylcyclohexane can also undergo elimination reactions, such as dehydrohalogenation reactions. These reactions involve the removal of the hydrogen atom from the carbon adjacent to the chlorine atom and the chlorine atom itself, resulting in the formation of an alkene.
Addition Reactions
Cis 1-chloro-2-methylcyclohexane can undergo addition reactions with a variety of reagents, such as hydrogen gas (H2) and Grignard reagents (RMgX). These reactions result in the addition of the reagent to the double bond of the alkene, forming the corresponding alkane or alkylated product.
Potential Side Reactions
Several potential side reactions can occur during the synthesis of cis 1-chloro-2-methylcyclohexane, including:*
-*Polymerization of 1-methylcyclohexene
This side reaction can occur if the reaction is carried out at high temperatures or in the presence of a strong acid catalyst.
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-*Formation of trans 1-chloro-2-methylcyclohexane
This side reaction can occur if the reaction is carried out in the presence of a weak acid catalyst or at low temperatures.
-*Formation of 1,2-dichloro-1-methylcyclohexane
This side reaction can occur if the reaction is carried out in the presence of a strong acid catalyst or at high temperatures.
These side reactions can impact the product yield and purity of the desired product. Therefore, it is important to optimize the reaction conditions to minimize the occurrence of these side reactions.
Applications and Uses: Cis 1 Chloro 2 Methylcyclohexane
Cis 1-chloro-2-methylcyclohexane is a versatile chemical compound with a wide range of applications in various industries and laboratories.
It is primarily used as a solvent due to its ability to dissolve a wide range of organic compounds. Its non-polar nature makes it an effective solvent for non-polar substances such as oils, fats, and waxes.
As a Starting Material
Cis 1-chloro-2-methylcyclohexane is also employed as a starting material in the synthesis of various other organic compounds. It can undergo a variety of reactions, including substitution, elimination, and addition reactions.
Environmental and Health Implications, Cis 1 chloro 2 methylcyclohexane
It is essential to note the potential environmental and health implications associated with the use of cis 1-chloro-2-methylcyclohexane. As a volatile organic compound (VOC), it can contribute to air pollution and may have adverse effects on human health if inhaled in high concentrations.
Proper handling and disposal procedures are crucial to minimize the environmental impact and protect human health. Adhering to established safety guidelines and regulations is essential when working with this compound.
Helpful Answers
What is the IUPAC name of cis 1 chloro 2 methylcyclohexane?
1-Chloro-2-methylcyclohexane
What is the boiling point of cis 1 chloro 2 methylcyclohexane?
162-164 °C
How is cis 1 chloro 2 methylcyclohexane synthesized?
By the addition of hydrogen chloride to 1-methylcyclohexene
