Organic Chemistry
Rank the following isomers from the one with the lowest boiling point to the one with the highest boiling point. Explain your answer.
Determine which of the following two compounds has the higher boiling point. Explain why that compound has the higher boiling point. 1-bromopropane and 1-chloropropane.
List these three compounds from the one with the lowest boiling point to the one with the highest boiling point. Pentane, propane and butane.
Determine which compound has the higher boiling point for each of the following pairs: (i): 3-methylpiperidine or 1,3-dimethylpyrrolidine, and (ii): 2,4-dimethylpyrrolidine or 4-methylpyrrolidin-2-one. Explain.
Determine which compound has the higher boiling point for each of the following pairs: CH3CH2CH2CH3 or (CH3)2CHCH3, and CH3CH2CH2CH3 or CH3CH2CH2CH2Cl. Explain.
Identify: (i) compounds that can form intermolecular hydrogen bonds; (ii) compounds that can form hydrogen bonds with water; (iii) compounds which you think are soluble in water. CH3(CH2)2CH3, CH2=CH-CH3, CH3CHO and CH3COOH.
Determine which compound has the higher boiling point for each of the following pairs: CH3OCH3 or CH3CH2OH, and CH3CH2CH3 or CH3CH2CH2CH3. Explain.
Show the intermolecular hydrogen bonding between two molecules of methanol and the intermolecular hydrogen bonding between two molecules of methylamine.
Determine which compound you expect to have the higher boiling point for each of the following pairs: (CH3)3C-CH2-C(CH3)3 or (CH3)2CH-CH2CH2CH2-CH(CH3)2, CH3(CH2)5CH3 or CH3(CH2)4CH2OH, and CH3OCH3 or CH3CH2OH. Explain your reasoning.
Determine which of the following compounds, cis-2,3-dibromobut-2-ene or trans-2,3-dibromobut-2-ene, has a higher boiling point, and which has zero dipole moment.
Between the given substances, dipropyl ether and hexan-1-ol, which one exhibits a higher boiling point?
Determine the atoms that act as hydrogen bond donors and acceptors in the molecule below.
Indicate the atoms that act as hydrogen bond donors and acceptors in the given molecule.
Determine which molecule is expected to have a higher boiling point in the given pair and explain your reasoning.
Which of the two given molecules would have the higher melting point and why?
Explain why benzene melts at a higher temperature even though it has a smaller molecular weight than toluene. Consider the possible interactions between molecules based on their shapes.
Despite having a high melting point, ionic compounds like sodium carbonate are quite soluble in water. Explain why.
Identify the compounds which can form intermolecular hydrogen bonds.
a. CH3CH2OH
b. (CH3)2NH
c. (CH3)3N
Explain:
a. Why does ethyl alcohol (78 °C) boils at a higher temperature than ethylamine (16 °C)?
b. Why does dimethylamine (7 °C) boils at a higher temperature than dimethyl ether (-24 °C)?
Explain why 1-heptanol boils at a higher temperature compared to 4-heptanol.
Predict which one of the given compounds has a stronger dipole moment and which one has a higher boiling point.
Explain why pyrrole (129 °C) boils at a higher temperature than N-methyl pyrrole (112 °C).
Arrange the given compounds in decreasing order of their boiling points (from highest to lowest).
Illustrate the hydrogen bonding present in propan-2-ol.
Which of the following substances, 1-bromohexane or 1-chlorohexane, has a higher boiling point?
From the two compounds below, which has a lower net dipole? Which is expected to have a lower boiling point?
Illustrate the hydrogen bonding that exists between (i) two molecules of triethylamine ((CH 3CH2)3N) and one molecule of water (H2O) and (ii) one molecule of ethoxyethane (CH 3CH2OCH2CH3) and two molecules of water (H 2O). Use dashes or broken lines to show the interactions.
Dipropyl ether and 1-hexanol are isomers. The two compounds have similar solubilities in water but have very different boiling points. Account for this observation.
The two N-containing isomers below have a boiling point difference of 19.0 °C. Meanwhile, the two O-containing isomers have a boiling point difference of 83.2 °C. The two N-containing isomers have a much smaller boiling point difference than the two O-containing isomers. Explain this observation.
Using the intermolecular forces of attraction concept, explain why propionic acid (bp = 141 °C) has a higher boiling point than propaneperoxoic acid (bp = 120°C; explodes) even though the former has a lower molecular weight than the latter.
