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AAMC FL 3 Question
Natasha_4902
#1 Posted : Friday, August 07, 2020 6:26:24 PM
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Hi,

For this question:

The relative thermodynamic stability of isomeric organic compounds can be inferred from which of the following types of experimental data?

A.Boiling points
B.UV–visible absorption spectra
C.Mass spectroscopic fragmentation patterns
D.Heats of combustion

Why is the answer D and not A? I thought structural isomers for example could have very different arrangement resulting in very different boiling points. Also why would more thermodynamically stable compounds release less heat upon combustion?

Thank you
INSTR_Katerina_102
#2 Posted : Saturday, August 08, 2020 3:03:06 AM
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Hi Natasha,

When discussing thermodynamic stability, I look for the lowest energy species, as I find an easier way to parse things is:

High energy = low stability
low energy = high stability

when I think of molecular stability, I think the strength of intramolecular bonds - oxygen is stable, as is methanol, despite having very different boiling points. As a result, boiling point can't really predict if something is unreactive or stable.

What is more telling, is how much energy a molecule releases upon reaction - if a molecule releases a lot of energy after burning, it must have been in a high energy, unstable state prior to reaction.

As a result, we would expect a low energy compound to release relatively little energy upon combustion, as it can't really react to reach a lower energy state than it already is at.

Please let me know if this is unclear,

Katt
Natasha_4902
#3 Posted : Saturday, August 08, 2020 6:51:21 PM
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Hi Katt,

So to confirm, if the question had asked for molecular stability then boiling point would have been a better choice?

Thank you
INSTR_Katerina_102
#4 Posted : Monday, August 10, 2020 4:39:27 AM
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Hi Natasha,

If it asked for molecular stability I would still have gone with D. Stability is distinct from the phase - we don't consider something that is solid to be more stable than something that is liquid or gas. We just think of stability as how much or how little energy something releases when it reacts.

I hope this clears things up!

Katt
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