5
$\begingroup$

The question asks us to select the compound with the smallest heat of hydrogenation per mole out of the following:

a) 1-butene

b) trans-2-butene

c) cis-2-butene

d) 1,3-butadiene

Since all four compounds form the same product (butane), a comparison without actual data should be possible. 1,3-butadiene is conjugated so it is the most stable compound and therefore its heat of hydrogenation should be the smallest.

But it requires 2 moles of hydrogen for complete conversion to butane. And the answer is actually trans-2-butene.

So would we consider each heat of hydrogenation "per mole of hydrogen" or "per mole of the given compound"? The question isn't clear about this and also, if we do consider it as "per mole of hydrogen" then is it correct to simply half the value heat of hydrogenation for 2 moles?

$\endgroup$
  • $\begingroup$ Related: Why is 2-methylpropene less in energy than its alkene counterparts? $\endgroup$ – Loong Jun 4 '15 at 18:15
  • $\begingroup$ Heat of hydration or heat of hydrogenation? Only hydrogenation leads to butane as the product. Hydration would potentially lead to different products for each molecule: (a) 1- or 2-butanol; (b) 2-butanol, (c) 2-butanol, (d) 1,4- or 1,3- or 2,3- butanediol. $\endgroup$ – Curt F. Jun 4 '15 at 19:19
  • $\begingroup$ @CurtF. I just realized I used both words in my question. Thanks for pointing it out, I've corrected it. $\endgroup$ – tkhanna42 Jun 5 '15 at 0:49
3
$\begingroup$

a comparison without actual data should be possible. 1,3-butadiene is conjugated so it is the most stable compound and therefore its heat of hydrogenation should be the smallest

No, 1,3-butadiene is not the most stable of these compounds, either for the whole molecule or on a per double bond basis (see below). The actual numbers (see table below) are too close, we need to look at some data in order to answer the question correctly.

The question asks us to select the compound with the smallest heat of hydrogenation per mole out of the following:

So would we consider each heat of hydrogenation "per mole of hydrogen" or "per mole of the given compound"?

Here is some data that will help answer the question.

enter image description here

(image source)

On a "per mole of given compound", trans-2-butene has the lowest heat of hydrogenation, 27.6 kcal/mole.

On a "per mole of hydrogen", 1,3-butadiene has a heat of hydrogenation between 28.2 (56.5/2) and 28.6 (57.1/2) kcal/mole, so trans-2-butene still has the lowest heat of hydrogenation at 27.6 kcal/mole.

So in this particular list of compounds, it doesn't matter whether the question is asking per mole of hydrogen or per mole of given compound, the answer is the same, trans-2-butene.

At first I thought "trick question", but then later thought, not really. The questioner did his homework and wanted the student to work out the answer both ways and see that since the you get the same answer whether you answer on a per mole compound or per mole hydrogen, you don't need to know whether the question is being asked on a per mole compound or per mole hydrogen basis.

$\endgroup$
  • $\begingroup$ is it fair to generalise that almost all conjugated hydrocarbons would have their electrons delocalised over the whole molecule and be able to share and make room for bonding? So making them less stable than a single (plain) double bond compound? (e.g. the above, 1-butene vs 1,3-butadiene) $\endgroup$ – bonCodigo Jul 25 '17 at 22:33
  • 1
    $\begingroup$ Yes and no. Yes, it is fair to generalize that most conjugated hydrocarbons would have their electrons delocalised over the whole molecule, but this makes them more stable. Fore example, as shown above, 1,3-pentadiene is more stable than 1,4-pentadiene due to this delocalization. $\endgroup$ – ron Jul 31 '17 at 2:12
1
$\begingroup$

To saturate one mole of 1,3-butadiene, there is a need of two mole hydrogen gas. In comparison with 1-butene, trans-2-butene, and cis-2-butene, these molecules only need 1 mole of hydrogen gas to be saturated to butane. Thus, 1,3-butadiene has the highest heat of hydrogenation. Stability of the remaining molecules can be used to measure qualitatively the trend of the heat of hydrogenation. Since trans is more stable among them, then it has the least heat of hydrogenation.

$\endgroup$
  • $\begingroup$ So by "heat of hydrogenation per mole", do we consider one mole of the compound to be hydrogenated? $\endgroup$ – tkhanna42 Jun 5 '15 at 10:51

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.