Of 2-methyl-2-butanamine and ethypropylamine, which has the highest boiling point and why?
1 Answer
Explanation:
You have isomeric primary and secondary amines. Hydrogen bonding can occur for both substances. Ordinarily, we would predict that the primary amine would be most involatile, and have the higher boiling point, because it has the greater opportunity for intermolecular interaction thru hydrogen bonding.
On the other hand, as the chain length of an organic molecule grows, there is greater possibility for chain-chain interactions, and boiling point increases. For the
I will stick my neck out, and claim that
But a scientist relies on data. I may be right, I may be wrong. But I have to consult the data. I just had a look at my trusty Aldrich catalogue, and it lists the boiling point of ethylpropylamine as
Evidently, hydrophobic interaction along the chain are greater than the effect of hydrogen bonding in this specific instance. Given that the amino function of the primary amine is sterically hindered, which would tend to reduce intermolecular ineraction, this can be rationalized.