2013年10月22日星期二

Questions about Cyclohexane

Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which being intermediates used in the production of nylon. 

On an industrial scale, cyclohexane is produced by reacting benzene with hydrogen. Producers of cyclohexane account for approximately 11.4% of global demand for benzene. Because of its unique chemical and conformational properties, it is also used in labs in analysis and as a standard. It has a distinctive detergent-like odor, reminiscent of cleaning product (in which it is sometimes used). Although Cyclohexane(CAS NO. :110-82-7) is used widely in our life, there are many questions about Cyclohexane in our mind. This article will list some questions about this chemical, I hope it will give you a little help.

First question from a chemistry student about how to make the molecular model of Cyclohexane?

If the model in your syllabus is a planar model:
1. Get 6 completely straight metal wires of equal length. The thinner the better. They represent the C-C bonds in the molecule.
2. Get some modelling clay (the soft and moldable kind) and make 6 small marble-sized balls out of it. these marbles represent carbon atoms. 
3. with the help of a protractor, measure 120 degrees and fasten the six wires using the clay-marbles to form a sort of hexagonal ring. 
4. You could attatch two small beads to each marble to represent hydrogen atoms. 

If the model is to be in accordance with the sasche-mohr theory wherin Cyclohexane has a puckered configuration, here's how you should do it: 
1. Get 6 completely straight metal wires of equal length. The thinner the better. They represent the C-C bonds in the molecule. 
2. Get some modelling clay (the soft and moldable kind) and make 6 small marble-sized balls out of it. these marbles represent carbon atoms. 
3. with the help of a protractor, measure 109.5 degrees and fasten the six wires using the clay-marbles to form a sort of ring which is not planar but resembles a chair or boat. 
4. You could attatch two small beads to each marble to represent hydrogen atoms.

Second about what are the difference between cyclohexane and benzene anybody?

Cyclohexane has no double bonds, it is just hexane joined up in a circle with two less hydrogens. Wheras benzene has a ring of dislocated electrons shown as three double bonds and so it is like cyclohexane but with only one hydrogen per carbon. In the other words, Cyclohexane is a ring of carbons single-bonded to each other with 2 hydrogens bonded to each carbon. Benzene is a ring of carbons with a double bond between every other carbon and one hydrogen bonded to each carbon. Benzene also has resonance between its bonds and is a flat molecule.
Can acetone have dipole-dipole interactions with cyclohexane?

Cyclohexane has no polar functional groups. Acetone has a polar carbonyl functional group. There would be no dipole-dipole interaction between the two because cyclohexane has no dipole moment. However, the dipole moment in the acetone (because the electron charge density favors the oxygen) will induce a momentary dipole in the cyclohexane (like a London dispersion force, but stronger because this is induced, whereas the London disperson force is due to chance). This dipole-induced dipole characterizes the intermolecular interaction between cyclohexane and acetone.

Is cyclohexane and cyclohexene soluble in water?

Cyclohexane is not soluble in, or miscible with water. Given the general rule of "like dissolves like", a quick check of the chemical structure of cyclohexane suggests that it is extremely low in polarity. It is a completely symmetrical saturated 6 membered ring containing carbon and hydrogen only. Nothing with sufficient electronegativity to cause significant polarity, and no asymmetry to cause any uneven electron distribution. Water on the other hand, not only contains highly electronegative oxygen, but also two hydrogen atoms, whose electron cloud is being pulled by the oxygen, so it is a dipole. 

I would disagree with some of the other contributors in terms of cyclohexene though. I wouldn't say it was "insoluble" in water, I would say it is "very sparingly soluble" in water. You can dissolve about 200 mg of cylcohexene into a litre of water at ambient temperature. The presence of the double bond in cyclohexene makes it (very very) slightly more polar than cyclohexane, which enables a tiny proportion to be solvated.

Want to learn more information about cyclohexane, you can access the guidechem.com. Guidechem.com is just a place for you to look for some chemicals.

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