1-Methylcyclohexene is a cyclic hydrocarbon with a molecular formula of C7H12. It is an unsaturated compound commonly used in organic synthesis and has a fruity odor.
| IUPAC Name | 1-Methylcyclohexene |
| Molecular Formula | C7H12 |
| CAS Number | 591-49-1 |
| Synonyms | Methyl-1-cyclohexene, 1-Methylcyclohex-1-ene, 1-Methyl-1-cyclohexene, 1-Methylcyclohexylene, 1-MCH, NSC 7411 |
| InChI | InChI=1S/C7H12/c1-7-5-3-2-4-6-7/h2-3,7H,4-6H2,1H3 |
1-Methylcyclohexene boiling point
The boiling point of 1-Methylcyclohexene is approximately 104-110°C at atmospheric pressure. This value is lower than the boiling point of cyclohexane, which is a saturated hydrocarbon with the same number of carbon atoms. This difference in boiling point is due to the presence of a double bond in 1-Methylcyclohexene, which results in weaker intermolecular forces compared to cyclohexane. The lower boiling point of 1-Methylcyclohexene makes it easier to separate from other compounds in a mixture by distillation.
1-Methylcyclohexene density g/ml
The density of 1-Methylcyclohexene is approximately 0.834 g/mL at 25°C (77°F). This value is lower than the density of water, which is 1.0 g/mL, indicating that 1-Methylcyclohexene will float on water.
1-Methylcyclohexene molar mass
The molar mass of 1-Methylcyclohexene is calculated to be approximately 96.17 g/mol. This value is derived from the sum of the atomic masses of all the atoms present in the molecule, which includes seven carbon atoms and twelve hydrogen atoms. The molar mass of 1-Methylcyclohexene is an important property used in the determination of the amount of the compound in a given sample.
Methylcyclohexene melting point
The melting point of methylcyclohexene is approximately -120°C (-184°F). This value is significantly lower than the melting point of cyclohexane, which is a saturated hydrocarbon with the same number of carbon atoms. The presence of a double bond in methylcyclohexene results in weaker intermolecular forces compared to cyclohexane, which accounts for the lower melting point.
Methylcyclohexene molecular weight
The molecular weight of methylcyclohexene is approximately 96.17 g/mol. This value is derived from the sum of the atomic masses of all the atoms present in the molecule.
Methylcyclohexene structure
The structure of methylcyclohexene consists of a cyclohexene ring with a methyl group attached to one of the carbons. The double bond in the cyclohexene ring gives the molecule its unsaturated character. The structure of methylcyclohexene can be visualized as a six-membered carbon ring with a double bond and a methyl group on one of the carbons.
Methylcyclohexene formula
The chemical formula of 1-Methylcyclohexene is C7H12. This formula represents the number and types of atoms present in the molecule. The formula can be used to determine the molar mass and other properties of 1-Methylcyclohexene.
| Appearance | Colorless to light yellow liquid |
| Specific Gravity | 0.834 at 25°C |
| Color | Colorless to light yellow |
| Odor | Fruity, sweet |
| Molar Mass | 96.17 g/mol |
| Density | 0.834 g/mL at 25°C |
| Melting Point | -120°C (-184°F) |
| Boiling Point | 104-110°C at atmospheric pressure |
| Flash Point | 7.8°C (46°F) |
| Water Solubility | Insoluble |
| Solubility | Soluble in organic solvents such as ethanol, ether, and acetone |
| Vapour Pressure | 35.8 mmHg at 25°C |
| Vapour Density | 3.3 (air=1) |
| pKa | ~43 |
| pH | Not applicable (1-Methylcyclohexene is a neutral molecule) |
Note: The values provided in the table are approximate and may vary depending on the source and conditions of measurement.
1-Methylcyclohexene Safety and Hazards
1-Methylcyclohexene is a hazardous chemical and can pose several safety risks if not handled properly. It is highly flammable and can form explosive mixtures with air. Exposure to 1-Methylcyclohexene can cause irritation to the eyes, skin, and respiratory system. It is important to wear proper personal protective equipment such as gloves and goggles when working with this chemical. In case of skin contact or ingestion, immediate medical attention should be sought. Proper storage and handling procedures should be followed to prevent accidental spills or releases. Overall, caution should be exercised when working with 1-Methylcyclohexene to ensure safety and prevent accidents.
| Hazard Symbols | F, Xi |
| Safety Description | Keep away from heat, sparks, open flames, and hot surfaces. Avoid breathing dust/fume/gas/mist/vapors/spray. Wear protective gloves/protective clothing/eye protection/face protection. Use explosion-proof electrical/ventilating/lighting/equipment. Keep container tightly closed. Store in a well-ventilated place. |
| UN IDs | UN2294 |
| HS Code | 290219 |
| Hazard Class | 3 |
| Packing Group | III |
| Toxicity | May cause irritation to the eyes, skin, and respiratory system. Prolonged or repeated exposure may cause skin dryness or cracking. |
1-Methylcyclohexene Synthesis Methods
Methylcyclohexene can be synthesized through various methods, including dehydration of 1-methylcyclohexanol and dehydrogenation of 1-methylcyclohexane.
- In the dehydration method, a strong acid catalyst, such as sulfuric acid, heats 1-methylcyclohexanol to remove a water molecule and form methyl cyclohexane. The reaction typically carries out under reflux conditions with a Dean-Stark trap, which removes the water as it forms.
- The dehydrogenation of 1-methylcyclohexane involves heating the compound with a suitable catalyst, such as copper or platinum, to remove two hydrogen atoms and form methylcyclohexene. This reaction typically carries out at high temperatures and pressures to promote the removal of the hydrogen atoms.
- The synthesis of methylcyclohexene involves the reaction of cyclohexene and methanol in the presence of a strong acid catalyst, such as sulfuric acid. Distillation is used to isolate the product after the reaction.
Overall, the synthesis of methylcyclohexene requires careful attention to reaction conditions and proper handling of reagents and catalysts to ensure a safe and efficient process.
Methylcyclohexene Uses
Methylcyclohexene has a variety of uses in different industries.
- Manufacturers use methylcyclohexene as a solvent in the production of paints, coatings, adhesives, and other chemical products.
- The fragrance industry utilizes methylcyclohexene as a key ingredient in the production of perfumes and scented products because of its pleasant and distinctive odor, which resembles the smell of freshly cut grass.
- Organic chemists use methylcyclohexene as a reagent in reactions involving the formation of carbon-carbon double bonds, such as in the synthesis of alkenes and dienes.
- Methylcyclohexene serves as a valuable tool in organic synthesis due to its unique structure and reactivity.
- Methylcyclohexene is a monomer used in the production of rubber and plastics, serving as a building block for larger polymer chains.
- Manufacturers use methylcyclohexene in the production of pesticides, herbicides, and other agricultural chemicals.
Overall, the versatile properties of methylcyclohexene make it an important component in various industrial processes and applications.
Questions:
What alcohol would be most appropriate for the synthesis of methylcyclohexene?
The most appropriate alcohol for the synthesis of methylcyclohexene would be 1-methylcyclohexanol. This is because 1-methylcyclohexanol is structurally similar to methyl cyclohexene, with the exception of an -OH functional group attached to one of the carbons. By removing the -OH group through dehydration, 1-methylcyclohexanol can be converted to methylcyclohexene.
Using 1-methylcyclohexanol as the starting material offers several advantages. First, it ensures that the desired product is formed, since the starting material and the desired product have similar structures. Second, using the same compound as both the starting material and the product simplifies the purification process, since the product can be isolated through distillation or other methods that take advantage of the differences in boiling points between the starting material and the product. Finally, using 1-methylcyclohexanol can also help to minimize waste and reduce costs, since it is often readily available and inexpensive.
What is the major product obtained from hydroboration-oxidation of methyl cyclohexene?
The major product obtained from hydroboration-oxidation of methyl cyclohexene is 1-methylcyclohexanol. Hydroboration-oxidation is a two-step process that involves the addition of borane (BH3) to the double bond of methylcyclohexene, followed by the oxidation of the resulting boron-containing intermediate with hydrogen peroxide (H2O2) and sodium hydroxide (NaOH).
During the first step of the reaction, borane adds to the double bond of methyl cyclohexene to form a boron-containing intermediate. The addition of borane occurs in an anti-Markovnikov fashion, meaning that the boron atom adds to the less substituted carbon of the double bond. The resulting intermediate is then oxidized in the second step of the reaction using hydrogen peroxide and sodium hydroxide, resulting in the formation of 1-methylcyclohexanol.
The hydroboration-oxidation reaction is a useful method for synthesizing alcohols from alkenes, as it proceeds with high regioselectivity and stereoselectivity. In the case of methylcyclohexene, hydroboration-oxidation results in the formation of a single product, 1-methylcyclohexanol, with no significant formation of any other byproducts.