Why is dichloromethane a good organic solvent?

In summary, the conversation discusses the differences in miscibility between water and dichloromethane with alcohols. It is noted that dichloromethane has a lower polarity compared to water, which allows it to mix better with organic compounds. This is especially useful for working with hydrophobic polymers, such as PLA. However, it should be noted that dichloromethane is toxic and precautions should be taken when handling it.
  • #1
birdstudyphys
2
0
I was working on my chem lab, this question occurred to me. Water and dichloromethane are both polar molecule. However, dichloromethane is able to mix with alcohols much better than water. Is there a polarity difference that caused the miscibility to be different?
 
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  • #2
birdstudyphys said:
I was working on my chem lab, this question occurred to me. Water and dichloromethane are both polar molecule. However, dichloromethane is able to mix with alcohols much better than water. Is there a polarity difference that caused the miscibility to be different?
Of course you are talking about higher weight alcohols, not CH3OH or C2H5OH, which are completely miscible with water. However CH2Cl2 is not as polar as water so it mix better than water with organic compounds.
 
  • #3
Yeh. CH2Cl2 is barely polar actually since C-Cl has deltaEN=0.5 where C-H gives a 0.4.
Much less polar than water for sure.. Well that explains it. Thanks. I was totally misled by my weird thinking... Egrrr.
 
  • #4
DCM is also an excellent solvent for convenient reasons like being more dense than water so it will be on the bottom in a separatory funnel if you do an aqueous workup and it is also easy to evaporate.
 
  • #5
However it is toxic, though the least of the chlorinated ethers. CH2Cl2 is partially miscible in water (it is not polar) , but its diffusivity in water is higher that water in CH2Cl2. IF working with hydrophobic polymers, it tends to be in general a good solvent. Specially for PLA.
 

FAQ: Why is dichloromethane a good organic solvent?

1. Why is dichloromethane commonly used as an organic solvent?

Dichloromethane, also known as methylene chloride, is widely used as an organic solvent due to its high solubility for a variety of organic compounds. It is also relatively inexpensive and has a low boiling point, making it easy to remove from the final product.

2. What makes dichloromethane a good solvent for organic reactions?

Dichloromethane is a polar aprotic solvent, meaning it has a dipole moment but does not participate in hydrogen bonding. This allows it to dissolve a wide range of polar and nonpolar organic compounds, making it suitable for a variety of reactions.

3. Is dichloromethane a safe solvent to use in a laboratory setting?

While dichloromethane is an effective solvent, it is also considered a hazardous chemical. It can cause irritation to the skin, eyes, and respiratory system, and should be handled with caution in a laboratory setting. Proper personal protective equipment and ventilation should be used when working with this solvent.

4. Can dichloromethane be used in place of other commonly used organic solvents?

Dichloromethane can often be substituted for other organic solvents such as chloroform, ethyl acetate, and diethyl ether. However, it is important to consider the specific properties and reactivity of each solvent before making a substitution.

5. What are some potential drawbacks of using dichloromethane as an organic solvent?

One potential drawback of using dichloromethane is its relatively low boiling point of 40°C. This can result in the solvent evaporating too quickly during reactions, leading to a decrease in reaction efficiency. Additionally, dichloromethane is known to be a volatile organic compound and can contribute to air pollution, so its use should be minimized when possible.

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