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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.