Which Structural Isomer Has the Highest Boiling Point?

[i_love_science]

Homework Statement

There are 4 different isomers of C3H9N. They have boiling points that range from 3°C to 48°C. Identify the isomers that you would expect to exhibit the lowest and highest boiling points. Explain your reasoning in terms of the intermolecular forces involved.

Relevant Equations

structural formulas

Why does the isomer C-C-C-N have the highest boiling point, rather than CC(N)C (where the N is attached to the second carbon)?
Isn't N able to form 3 H-bonds in both cases? Thanks.

 

[Borek]

What has larger contact area: two pencils, or two balls?

 

[Physics guy]

Larger contact area; more Force of attraction, so ...

 

[i_love_science]

Larger contact area; more Force of attraction, so ...

Does the N in CC(N)C has less contact area because of the 3 C chain?

 

[Physics guy]

Does the N in CC(N)C has less contact area because of the 3 C chain?

We are not talking bout the area of a single atom, it does not concern us here. We are trying to identify which of the isomers has larger area to have contact with another molecule. This will cause attraction due to wander walls force. Note that there are also other factors that come into play like Hydrogen bonding etc

 

[i_love_science]

We are not talking bout the area of a single atom, it does not concern us here. We are trying to identify which of the isomers has larger area to have contact with another molecule. This will cause attraction due to wander walls force. Note that there are also other factors that come into play like Hydrogen bonding etc

So the hydrogen bonding involving N is only one factor determining the force of attraction, other intermolecular forces play an major role as well?
Thanks, I understand now.