Rank the following compounds from lowest boiling point to highest boiling point.

Question

BlackTom AI · Accepted Answer

When ranking boiling points among compounds of similar molecular weight, several factors come into play: hydrogen bonding capability, molecular polarity, and molecular symmetry/branching which affects surface area.

Option a: 'C < A < B' would mean A has a higher boiling point than B. If A possesses more accessible hydrogen-bond donors/acceptors or a larger, less-branched surface area than B, this could push A’s bp above B. However, given typical amide-like structures with substantial hydrogen-bonding networks, a large, highly branched species tends to disrupt efficient packing and lower bp, while a less-branched counterpart with similar functional groups often has a higher bp due to stronger intermolecular interactions and greater surface contact. Therefore, this ordering seems inconsistent with the expectation that the least branched species (A) would exhibit the highest bp, not B.

Option b: 'C < B < A' represents the idea that C is the most branched or least able to engage in effective intermolecular interactions, leading to the lowest boiling point, while A is the least branched or most capable of hydrogen bonding, giving it the highest boiling point. This aligns with the general trend: increasing branching lowers boiling point by reducing surface area and packing efficiency, whereas strong hydrogen bonding and greater surface contact raise boiling points. Here, C would be the smallest effect due to steric hindrance and branching, B would be intermediate, and A would exhibit the strongest intermolecular attractions, yielding the highest bp.

Option c: 'B < C < A' would imply C has a higher bp than B. If C were more capable of hydrogen bonding or presented a larger, less hindered surface than B, this could occur. But given the visual cues of increased branching or steric bulk in C relative to B, C would typically fail to surpass B in bp, making this ordering unlikely.

Option d: 'A < B < C' would place A as the lowest bp and C as the highest, which contradicts the expectation that A, being less hindered or possessing favorable H-bonding, would have a stronger intermolecular interaction and thus a higher bp than C. This sequence generally runs against the standard pattern for similarly functionalized, progressively more branched molecules.

In summary, the most plausible trend in such a set, considering branching and hydrogen-bonding potential, is that C has the lowest boiling point, B is intermediate, and A has the highest boiling point. The option that expresses 'C < B < A' matches this reasoning and is the sequence that reflects the impact of branching and hydrogen-bonding on boiling points across these structures.

CHM1052 - MUM S2 2025 CHM1052 2022 practice exam 1

Rank the following compounds from lowest boiling point to highest boiling point.

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