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  • Voiceover: Before we get into the physical properties

  • of aldehydes and ketones, I just wanted to cover

  • where the names for those functional groups come from.

  • So, one way to make aldehydes and ketones

  • is to oxidize alcohol.

  • So if we start over here on the left

  • and we have methanol, we can oxidize that to

  • methonal over here on the right.

  • Also called formaldehyde.

  • And if we analyze the atoms here,

  • one carbon on the left and one carbon on the right,

  • one oxygen on the left and one oxygen on the right,

  • four hydrogens on the left and only two on the right,

  • so a loss of two hydrogens can convert methonol

  • to methonal, and so the name of aldehyde

  • comes from these words here.

  • So if I write alcohol and then dehydrogenatum,

  • which refers to the fact that we are losing hydrogens.

  • If you look closely you can see the name for aldehyde.

  • If you take the name al from alcohol,

  • and then this portion of this word,

  • and then add an e on,

  • you get the name aldehyde.

  • So that's the idea.

  • You can also make ketones.

  • So if I oxidize this alcohol on the left to propanol,

  • also called isopropanol or isopropyl alcohol

  • and then finally rubbing alcohol.

  • If you oxidize this molecule,

  • then you get this molecule over here on the right.

  • So there are three carbons ...

  • So a three carbon ketone is called a propanone

  • and of course no one usually calls this propanone.

  • This is a famous molecule.

  • This is acetone.

  • And the old German word for acetone ...

  • If you spell out the old German word for acetone,

  • it's easy to see where the word ketone comes from, right?

  • 'Cause if I take this right here and add an e on,

  • I get ketone.

  • So just a little bit of insight into those names

  • which I think is pretty interesting.

  • In terms of physical properties,

  • let's use these last two molecules here to

  • describe boiling points of aldehydes and ketones.

  • Let's take two propanol over here on the left,

  • and let's compare the boiling point of

  • of two propanol to acetone.

  • So when you are talking about boiling point,

  • you need to think about intermolecular forces,

  • so the forces between molecules.

  • So let's draw out two molecules of isopropanol here.

  • Let's go ahead and draw one, so we have our

  • oxygen, we have our hydrogen right here.

  • Now we know that oxygen is more electronegative

  • than hydrogen, so the electrons in this bond

  • are going to be pulled closer to the oxygen

  • giving the oxygen a partial negative charge

  • and giving this hydrogen a partial positive charge.

  • If another molecule of isopropanol comes along,

  • let's go ahead and show that,

  • it has the same situation, right?

  • The oxygen is partially negative

  • and the hydrogen is partially positive.

  • We know that opposite charges attract.

  • Right, so this partial positive charge

  • is attracted to this partial negative charge,

  • and this intermolecular force is called hydrogen bonding.

  • So this is an example of hydrogen bonding,

  • which we know is between hydrogen and

  • a very electronegative atom like

  • fluorine, oxygen, or nitrogen,

  • and also this hydrogen has to be bonded

  • to another electronegative atom,

  • so here we have oxygen.

  • So this is an example of hydrogen bonding.

  • The strongest type of intermolecular force.

  • It takes a lot of energy to pull these molecules apart,

  • so it takes a lot of heat.

  • And so the boiling point of isopropanol is relatively high.

  • The boiling point is approximately 83 degrees Celsius.

  • So let's compare that situation with acetone.

  • So let's go ahead and draw out acetone here.

  • And so here is one molecule of acetone.

  • If we think about oxygen compared to this

  • carbonyl carbon here, oxygen is more electronegative,

  • and so there is going to be a polarization, right?

  • So the oxygen is going to withdraw electron density

  • making the oxygen partially negative.

  • It is taking electron density away from this carbon,

  • so this carbonyl carbon is partially positive

  • and so we have a dipole situation.

  • So this molecule has a dipole moment.

  • And if we think about another molecule of acetone,

  • right so another one has the exact same situation, right?

  • The oxygen is partially negative,

  • this carbonyl carbon is partially positive,

  • and so we have an attraction between

  • this partially negative oxygen

  • and this partially positive carbon.

  • So there is an attraction between these two dipoles.

  • So we call this dipole-dipole interaction,

  • which is another type of intermolecular force.

  • Actually hydrogen bonding is just an example

  • of a very strong dipole-dipole interaction.

  • So dipole-dipole interactions are not as strong

  • as hydrogen bonding, so molecules of acetone

  • aren't attracted to each other as much as

  • molecules of isopropanol, so it doesn't take

  • as much energy to pull apart molecules of acetone,

  • and therefore the boiling point is lower.

  • The boiling point of acetone is

  • approximately 56 degrees Celsius.

  • Both of these temperatures are above room temperature,

  • but both of these boiling points are above room temperature

  • so at room temperature and pressure,

  • two propanol and acetone are both liquids.

  • Let's look at some other molecules

  • and let's compare them here.

  • So we have all molecules with three carbons.

  • So over here on the left, this is propane.

  • And the boiling point for propane is approximately

  • negative 42 degrees Celsius,

  • so that's well below room temperature.

  • Room temperature is approximately

  • between 20 and 25 degrees Celsius,

  • and so since the boiling point for propane

  • is well below room temp, the propane is already a gas.

  • So this state of matter of propane is a gas here.

  • It terms of intermolecular forces,

  • the only intermolecular forces holding together

  • alkanes are London dispersion forces.

  • So let's go ahead and write that up here.

  • Next, let's analyze an aldehyde.

  • Right so a three carbon aldehyde,

  • one, two, three, so this must be proponal.

  • The boiling point for proponal is

  • approximately 50 degrees Celsius.

  • Once again, higher than room temperature,

  • so proponal is a liquid.

  • We have just analyzed acetone.

  • Our next boiling point is approximately 56 degrees,

  • and for both proponal and for acetone,

  • you have the dipole-dipole interaction between molecules.

  • So we already covered acetone.

  • The same situation exists for this aldehyde.

  • So we have a partial negative here and

  • a partial positive right here,

  • and so there is going to be dipole-dipole interaction

  • between molecules of proponal.

  • So we have once dispersion for our alkane,

  • and then for our aldehyde and ketone

  • we have dipole-dipole interaction.

  • And then finally we have another alcohol.

  • So instead of two propanol, this is one propanol,

  • which has a boiling point of approximately 97 degrees.

  • And one proponal also has of course hydrogen bonding.

  • So we can see that the boiling points reflect

  • the type of intermolecular force.

  • Hydrogen bonding is stronger than dipole-dipole interaction,

  • and so therefore the boiling points for alcohols

  • are higher than the boiling points for aldehydes or ketones,

  • but aldehydes and ketones have a higher boiling point

  • than alkanes because dipole-dipole interactions

  • are stronger than London dispersion forces.

  • So let's look at solubility next.

  • I just did boiling point,

  • now lets think about solubility in water.

  • So let's go ahead and write that.

  • And once again, let's think about acetone as our example.

  • And so if we draw this out, here's one molecule

  • of acetone and I can go ahead and put my lone

  • pairs of electrons in there on my oxygen,

  • once again, the oxygen gets a partial negative charge

  • so the oxygen withdraws some electron density

  • so it gets a little more negative and

  • this carbonyl carbon gets a little bit positive,

  • and so we have this polarized situation

  • in our acetone molecule.

  • The thing about solubility and water ...

  • I'll go ahead and draw the dot structure for water.

  • We know that water is also polarized here,

  • so these electrons and this bond

  • are pulled closer to the oxygen.

  • So these electrons are pulled closer to the oxygen

  • giving the oxygen a partial negative,

  • and giving this hydrogen a partial positive.

  • So we can see there is going to be an attractive force

  • between this partial negative and this partial positive.

  • In terms of intermolecular forces,

  • we should recognize that as hydrogen bonding.

  • So this is hydrogen bonding right here.

  • Because of that, we know that acetone

  • is going to be soluble in water.

  • So we have hydrogen bonding.

  • Now one quick point that I have forgot to mention

  • in the previous example.

  • Some people are confused as to why molecules

  • of acetone can't hydrogen bond with themselves,

  • so let's go back up here and look at those

  • two molecules again.

  • So if I think about the possibility

  • of hydrogen bonding here,

  • there is a hydrogen connected to this carbon,

  • but that's the point.

  • This hydrogen is connected to a carbon.

  • It is not connected to something like oxygen,

  • which is what we had over here.

  • So hydrogen bonding between molecules of acetone

  • is not possible because the hydrogen is bonded

  • to a carbon and not to something like an oxygen.

  • So even though hydrogen bonding between

  • molecules of acetone is not possible,

  • hydrogen bonding between acetone and water is possible,

  • and so acetone is going to be soluble in water.

  • So same idea for other small aldehydes and ketones.

  • Small aldehydes are ketones are going to be

  • relatively soluble in water.

  • However, as you increase the chain length,

  • so if you think about the alkyl groups

  • attached to either a ketone or an aldehyde,

  • so let's just look at the alkyl groups here.

  • As you increase the number of carbons

  • that are bonded to an aldehyde or ketone,

  • that increases the non-polar character of the molecule.

  • So as you increase the chain length,

  • you make the molecule more non-polar,

  • and therefore you are going to decrease

  • the solubility in water.

Voiceover: Before we get into the physical properties

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B1 中級

醛類和酮類的物理性質。 (Physical properties of aldehydes and ketones)

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    吳思賢 發佈於 2021 年 01 月 14 日
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