I'm taking a chemistry test on around 3 hours and there's one question that I wasn't able to google or get from the text books.

Which of the following is soluble in water and which gives more energy? Why?
Then it gives me glucose and butanoic acid. Google says they are both soluble on water and it doesn't say shit about energy. It's driving me crazy.

7 years ago

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First off, what kind of chemistry is it? (Organic, Biochemistry, Physical Chemistry, etc)

By energy, the question could be referring to several context-specific things:

  1. Metabolism (in general, fats give more energy than carbohydrates, but you would have to do the calculations for butanoic acid and glucose for direct comparison as butanoic acid would be a late-stage product of fat catabolism and would give less energy than a fatty acid)
  2. Thermochemistry related energies (Heat of combustion, for example. According to wiki, glucose wins that one).
7 years ago
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Organic, and I suppose it's related to metabolism, given that we never saw termochemistry energies.

7 years ago
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Hmm... it's unusual to do metabolic energy gains in detail in organic chemistry, but if you use ATP as energy count and do full catabolism down to CO2, I think glucose wins over butanoic acid (30 ATP vs 22 or so, using 30 instead of 36 theoretical glucose gain). Don't take my word for it though, been a while since I did these things.

Another possibility is that they want you to discuss the dissolution of the compounds in water, in which case, glucose, as it forms more hydrogen bonds, will probably have a more favourable dissolution profile (unless a butanoate overcomes it, as it's a pure charge solvating).

7 years ago
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I'll keep it in mind, thanks a bunch!

7 years ago
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Sorry, I mastered only nuclear fusion.

7 years ago
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SCIENCE!

7 years ago
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Solubility in water is directly related to the amount of polar groups a givem molecule contains.
Butanoic acid contains 1 polar group (the -OH)
Glucose has 5 polar groups (all of them -OH)
Therefore glucose is more soluble in water than butanoic acid

In aerobic respiration, one molecule of glucose gives a net yield of 36 ATP molecules (a total of 38 but 2 are used to recover NADH)
Through fatty acid metabolism, butanoic acid would yield only one ATP as it's too short for more than one cycle (each cycle requires two -CH2- groups and butanoic acid only has 3)
So glucose gives more energy

Source: I'm a biotech student (I admit my organic chemistry is a little rusty so take all this with a grain of salt)

7 years ago
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Thanks!

7 years ago
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I don't remember much about chemistry, but I know that dropping some water on acid will create a reaction that releases a lot of energy. But nothing of the sort happens if you drop a bit of acid in water. Even so, this alone doesn't answer your question, so... Just ignore this post.

7 years ago
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True! The hydration of acid ions produces heat which may make the water start to boil (very dangerous because drops of acid may end up flying everywhere)
However it is important to remember that this only happens with acids that dissociate completely into ions (so called strong acids, like sulfuric) Butanoic acid is not a strong acid so it can be diluted in water safely.
("Fun" fact, butanoic acid is responsible for the smell of human vomit)

For anyone curious about the exact chemistry: http://chemistry.stackexchange.com/questions/893/why-first-water-and-then-acid

(Oops sorry, I didn't mean to write this much haha)

7 years ago
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Wow, you really like chemistry! Thanks for the data :)

7 years ago
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