Which has the highest boiling point?

In summary, the conversation discusses the boiling points of three molecules: 3-pentanone, 1-butanol, and butanal. The question is which of these has the highest boiling point. One person argues that 3-pentanone should have the highest boiling point due to its molecular weight and dipole-dipole attraction. However, another person points out that when they searched online, butanol was listed as having the highest boiling point. The discussion then shifts to the types of intermolecular forces present in these molecules, with the conclusion that hydrogen bonding is stronger and applies to alcohols. However, it is noted that this is not always the case and other factors such as branching can also affect boiling points.
  • #1
Sall1230
10
0

Homework Statement


Which one of these had the highest boiling point?
A. 3-Pentanone B. 1-Butanol C. Butanal

Homework Equations

The Attempt at a Solution


The answer should be 3-pentanone because
1- it's molecular weight is approx 76 compared to the other which has approx 64
2 - because of the dipole-dipole attraction.

However when I googled the boiling points for each one it says that Butanol has the highest. Why is it that?
 
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  • #2
What kinds of intermolecular bonds/interactions/forces do you know?
 
  • #3
Borek said:
What kinds of intermolecular bonds/interactions/forces do you know?

I know the dipol-dipol attraction which is between carbon and oxygen and the Hydrogen bond which is as a result of unshared pare of electrons and the hydrogen.
 
  • #4
Which is stronger? And which apply to which of these molecules?
 
  • #5
Borek said:
Which is stronger? And which apply to which of these molecules?

Hydrogen bond is stronger and it applies to alcohols.
So, does that mean that alcohols always have higher boiling points than ketones/aldehydes regardless of their molecular weight?

However, if an alcohol has branching and the ketone does not, then the alcohol will have lower boiling points am I correct?
 
  • #6
Sall1230 said:
does that mean that alcohols always have higher boiling points than ketones/aldehydes regardless of their molecular weight?

Not necessarily.

Actually this is quite tricky, as such simplified comparisons work best with the assumption "all other things kept constant".

In this particular case all three molecules are reasonably similar when it comes to the molecular mass, so the answer is more or less obvious, hydrogen bonding should make the difference. But when the mass difference becomes larger things become less obvious.
 

1. What determines the boiling point of a substance?

The boiling point of a substance is determined by its intermolecular forces, specifically the strength of its hydrogen bonds, dipole-dipole interactions, and London dispersion forces. The stronger these forces are, the higher the boiling point will be.

2. Is there a relationship between molecular weight and boiling point?

Yes, generally as the molecular weight of a substance increases, so does its boiling point. This is because larger molecules have more electrons and a larger surface area, which leads to stronger intermolecular forces.

3. Why do similar substances have different boiling points?

The boiling point of a substance is not only determined by intermolecular forces, but also by the shape and structure of its molecules. Even substances with similar molecular weights can have different boiling points if their molecules are arranged differently.

4. Can the boiling point of a substance change?

Yes, the boiling point of a substance can change depending on external factors such as pressure and temperature. For example, increasing pressure can raise the boiling point of a substance, while decreasing pressure can lower it.

5. Are there any exceptions to the relationship between intermolecular forces and boiling point?

Yes, there are some substances that have higher boiling points than predicted by their intermolecular forces. This is due to the presence of hydrogen bonding, which is a very strong intermolecular force that can significantly increase the boiling point of a substance.

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