QUESTION IMAGE
Question
your turn 1: which imf/bp is greater
based on the guidelines to the right, let’s determine which of the following substances below would have the higher boiling point. molar masses are given in parenthesis.
ch₃ - o - ch₃ (46.1 g/mol) or
ch₃nh₂ (31.1 g/mol)
remember to start by looking at which forces are the most important.
can either substance hydrogen bond?
yes, and because of hydrogen bonding, ch₃nh₂ has intermolecular forces that are stronger than ch₃ - o - ch₃
no, neither can form hydrogen bonds, so you’ll need to look at the other types of intermolecular forces
which substance has the stronger total intermolecular forces/the higher boiling point?
- first look to see if the substance can hydrogen bond. if so, it likely has the strongest intermolecular forces (e.g., hf > hcl).
- if you are comparing two molecules of very different molar masses, london dispersion forces are more important (e.g., hbr > hcl).
- if you are comparing two molecules of very similar molar mass, dipole - dipole forces are more important. the molecule with the greater dipole - dipole forces (the greatest electronegativity difference between the atoms within the molecule) will have the greatest boiling point.
Step1: Analyze hydrogen bonding capability
Hydrogen bonding occurs when a hydrogen atom is bonded to a highly electronegative atom (N, O, F). In \(CH_{3}NH_{2}\), the hydrogen is bonded to nitrogen, so it can form hydrogen bonds. In \(CH_{3}-O - CH_{3}\), there is no hydrogen bonded to a highly electronegative atom (the hydrogens are bonded to carbon), so it cannot form hydrogen bonds.
Step2: Compare intermolecular forces
Since \(CH_{3}NH_{2}\) can form hydrogen bonds (a strong type of intermolecular force) and \(CH_{3}-O - CH_{3}\) cannot, \(CH_{3}NH_{2}\) will have stronger intermolecular forces. Stronger intermolecular forces lead to a higher boiling point as more energy is required to overcome these forces to convert the liquid to a gas.
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Yes, and because of hydrogen bonding, \(CH_{3}NH_{2}\) has intermolecular forces that are stronger than \(CH_{3}-O - CH_{3}\)