Boiling point of ethers and alkanes

In summary, the rule of thumb for ethers having higher boiling points than alkanes due to dipole-dipole interactions is not always true for larger alkanes with 5 or more carbons. This is because longer, unbranched alkanes can have more Van der Waals interactions, leading to a higher boiling point. This is evidenced by the fact that hexane has a higher boiling point than ethyl-propyl-ether, and butane has a higher boiling point than ethyl methyl ether. Therefore, the rule only applies in certain cases and should not be taken as a definitive principle.
  • #1
Queequeg
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My organic chemistry textbook says that ethers generally have higher boiling points than alkanes because of dipole-diole interactions, but why then does hexane have a higher boiling point than ethyl-propyl-ether? Is this principle then not true for larger alkanes with 5 or more carbons? Diethyl ether also has a higher boiling point than pentane, but then butane has a higher B.P than ethyl methyl ether.
 
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  • #2
2 reasons:

1) As an alkane or alkyl gets longer but does not branch, its BP increases b/c it can have more Van der Waals interactions; thus, ethyl-propyl-ether has a higher bp than ethyl methyl ether;;; hexane has a higher BP than pentance, etc. hope this helps.
 
  • #3
Queequeg said:
My organic chemistry textbook says that ethers generally have higher boiling points than alkanes because of dipole-diole interactions

IMHO "generally" suggests it is just a rule of thumb, and as such can often fail.
 

1. What is the difference between the boiling point of ethers and alkanes?

Ethers typically have a lower boiling point than alkanes due to their weaker intermolecular forces. Ethers have dipole-dipole interactions, while alkanes only have London dispersion forces.

2. How does the length of the carbon chain affect the boiling point of alkanes?

As the length of the carbon chain increases, the boiling point of alkanes also increases. This is because longer carbon chains have more surface area, allowing for stronger London dispersion forces between molecules.

3. Why do branched alkanes have a lower boiling point than straight-chain alkanes?

Branched alkanes have a lower boiling point because their branching reduces surface area and therefore weakens the London dispersion forces between molecules.

4. How does the presence of double or triple bonds affect the boiling point of ethers and alkanes?

The presence of double or triple bonds in ethers and alkanes decreases their boiling point. This is because double and triple bonds disrupt the ability of molecules to pack tightly and form strong intermolecular forces.

5. Can the boiling point be used as a reliable way to identify a specific ether or alkane?

No, the boiling point alone cannot be used to identify a specific ether or alkane. Other factors such as molecular weight, functional groups, and isomers must also be taken into consideration.

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