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Properties of Alcohols - Chemistry, Class 12 Video Lecture
FAQs on Properties of Alcohols - Chemistry, Class 12 Video Lecture
| 1. What are the properties of alcohols? |  |
Ans. Alcohols have several properties that distinguish them from other organic compounds. Some important properties of alcohols include:
- Alcohols have higher boiling points compared to similar-sized hydrocarbons due to hydrogen bonding between alcohol molecules.
- They have the ability to dissolve in both polar and nonpolar solvents, making them versatile in various chemical reactions.
- Alcohols are generally less dense than water.
- They can undergo oxidation reactions to form aldehydes, ketones, or carboxylic acids.
- Alcohols can act as both acids and bases, undergoing reactions with strong bases and acids, respectively.
| 2. How does hydrogen bonding affect the physical properties of alcohols? | |
Ans. Hydrogen bonding plays a significant role in determining the physical properties of alcohols. Due to the presence of a highly polar O-H bond, alcohols can form hydrogen bonds with other alcohol molecules or other compounds containing hydrogen bond acceptors. This leads to:
- Higher boiling points compared to similar-sized hydrocarbons, as more energy is required to break the hydrogen bonds and convert the liquid to a gas phase.
- Increased solubility in polar solvents, as the hydrogen bonds can form with the solvent molecules.
- Enhanced intermolecular forces and stability, resulting in a more ordered and structured liquid phase.
| 3. How do alcohols dissolve in both polar and nonpolar solvents? | |
Ans. Alcohols possess a polar O-H bond due to the electronegativity difference between oxygen and hydrogen. This polar nature allows alcohols to dissolve in polar solvents, such as water, through hydrogen bonding. The oxygen atom of the alcohol molecule can form hydrogen bonds with the hydrogen atoms of water molecules.
On the other hand, alcohols also have a nonpolar hydrocarbon chain. This nonpolar region enables alcohols to dissolve in nonpolar solvents, such as hydrocarbons, oils, or fats. The nonpolar hydrocarbon chain interacts with the nonpolar solvent molecules through weak dispersion forces or Van der Waals forces.
Thus, the dual nature of alcohols, having both polar and nonpolar regions, allows them to dissolve in a wide range of solvents.
| 4. How do alcohols act as both acids and bases? | |
Ans. Alcohols can exhibit acidic or basic behavior depending on the reaction conditions. When reacting with strong bases, alcohols can act as acids by donating a proton (H+ ion). This process is known as deprotonation. For example, in the presence of a strong base like sodium hydroxide (NaOH), an alcohol molecule can donate a proton to the hydroxide ion (OH-) to form water and the corresponding alkoxide ion.
On the other hand, alcohols can also react with strong acids and act as bases by accepting a proton. This is known as protonation. For instance, in the presence of a strong acid like hydrochloric acid (HCl), an alcohol molecule can accept a proton from the acid to form a positively charged alkyl oxonium ion.
The ability of alcohols to act as both acids and bases is due to the presence of the polar O-H bond, which can either donate or accept a proton depending on the reaction conditions.
| 5. How do alcohols undergo oxidation reactions to form aldehydes, ketones, or carboxylic acids? | |
Ans. Alcohols can undergo oxidation reactions, where the oxygen atom in the O-H bond gains electrons or hydrogen atoms are removed. Depending on the degree of oxidation, alcohols can be oxidized to form aldehydes, ketones, or carboxylic acids.
Primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids. This oxidation process often involves the use of oxidizing agents such as potassium dichromate (K2Cr2O7) or acidified potassium permanganate (KMnO4).
Secondary alcohols can be oxidized to ketones using similar oxidizing agents.
Tertiary alcohols, lacking a hydrogen atom on the carbon atom bearing the hydroxyl group, cannot undergo oxidation reactions.
The oxidation of alcohols involves the breaking of the O-H bond and the formation of a new functional group, such as a carbonyl group (C=O) in aldehydes and ketones or a carboxyl group (COOH) in carboxylic acids.
Text Transcript from Video
Let's start with physical
properties of alcohols.
And so we're going to
compare, in this case,
alcohols to alkanes And this
alkane on the left here,
two carbons, so this
is of course ethane.
On the right, if we take
off one of those hydrogens
and replace it with an OH, we of
course have ethanol right here.
So let's start with
the boiling point.
So the boiling point of ethane
is approximately negative 89
degrees Celsius.
And since room temperature
is somewhere around 20 to 25
degrees Celsius,
at room temperature
we are much higher than the
boiling point of ethane,
which means it's already boiled.
It's already turned into a gas.
So at room temperature and
room pressure, ethane is a gas.
Ethanol, however, has a
much higher boiling point,
somewhere around
78 degrees Celsius.
And once again, since
room temperature
is somewhere around 20 to 25,
the boiling point of ethanol
is much higher than
room temperature.
So at room temperature and
pressure ethanol is a liquid.
It hasn't boiled yet.
And these large differences
in boiling points
between these two
molecules can be attributed
to the intermolecular
forces that are present.
So if two molecules of
ethane are interacting,
really the only
intermolecular force
that's holding those
molecules together
would be London
dispersion forces,
which are the weakest of
the intermolecular forces.
So it's relatively easy to
pull part two ethane molecules.
And that accounts for the
very low boiling point.
Doesn't take a lot of
energy to pull them apart.
So it's easy for it
to turn into a gas.
Ethanol, however, has a
much higher boiling point,
which means it's much harder
to pull those molecules apart.
It takes more energy.
So let's look at why ethanol
has such a higher boiling point.
So if I show two ethanol
molecules interacting,
so here is one ethanol
molecule, and let's go ahead
and draw another ethanol
molecule right here.
And if I think about the
oxygen hydrogen bond,
I know that's a
polarized covalent bond.
I know that there's a large
difference in electronegativity
between the oxygen
and the hydrogen.
Oxygen's much more
electronegative,
which means the electrons
in the bond between oxygen
and hydrogen are going to be
much closer to the oxygen atom,
giving the oxygen atom a
partial negative charge.
So these electrons in this bond
between oxygen and hydrogen
are going to move away
from the hydrogens.
And hydrogen is going to lose a
little bit of electron density,
leaving it relatively positive.
So we give it a partial
positive charge.
It's the same thing for the
other ethanol molecule, right?
Partially negative
oxygen, partially positive
hydrogen, and we know that
opposite charges attract.
So the partially
positive hydrogen
is attracted to the
partially negative oxygen.
And so there's a strong
intermolecular force
that holds those two
molecules together.
And that, of course,
is hydrogen bonding.
So there's hydrogen bonding
between alcohol molecules.
And since hydrogen bonding's the
strongest intermolecular force,
it's relatively difficult to
pull those molecules apart.
It takes a lot of energy,
takes a lot of heat,
and that's why the
boiling point of ethanol
is so much higher than the
boiling point of ethane,
and it also accounts
for the state of matter.
What about solubility?
So is ethanol soluble in water?
And of course, it is.
And the reason why is
hydrogen bonding, once again.
So if we draw a water
molecule in here,
I know that the water molecule
is polarized in the same way
that the alcohol molecule is.
So the hydrogen is
partially positive,
and the oxygen right over
here is partially negative.
And so once again,
opposite charges attract.
The hydrogen is attracted
to this oxygen here.
And so because of
hydrogen bonding,
there's interaction
between the water molecule
and in between the
alcohol molecules.
So the water molecule is polar.
So if you want to think about
it in terms of polarity,
because of the difference
in electronegativity,
water is a polar molecule,
ethanol is a polar molecule,
and like dissolves like.
So these two molecules will
be soluble in each other.
So if I look at the
structure of ethanol,
the reason why it
is soluble in water
is because of this
portion of the molecule,
this hydroxyl group, this OH.
It's the differences
in electronegativity
that allow the hydrogen bonding.
So this portion of the
molecule is the polar portion
of the molecule.
And this portion of the
molecule is the part
that loves water, which
is why it is soluble.
So if it loves water, we say
it's hydrophilic, hydro meaning
water, phil meaning
love, so hydrophilic.
Whereas this portion
over here on the left,
this is more of an alkane
type of environment,
a non-polar type of environment.
So this part of the
molecule is scared of water.
So it's hydrophobic.
So we have the hydrophobic
portion of our alcohol
molecule, and we have
the hydrophilic portion
of the alcohol molecule.
Now, we know that
like dissolves like,
so non-polar will not
dissolve in polar.
But as long as we have a
relatively small number
of carbon atoms in
our alkyl group,
the OH group is polar
enough for the alcohol
to be soluble in water.
Now, if you have a large
number of carbon atoms,
your molecule is more
non-polar than polar.
And so alcohols will stop
being soluble in water
if they have a lot of
carbon atoms on them.
So let's look at now the
preparation of alkoxides.
So let's look at an alcohol.
So here we have our alcohol.
And if we react our alcohol
with a strong base--
So we'll give it a lone pair
of electrons, a negative 1
formal charge, so we
have a strong base here.
And our strong base is
going to take this proton
and leave these electrons
behind on this oxygen.
So now we have an
oxygen that used
to have two lone
pairs of electrons
and now has three lone pairs.
That gives it a negative
1 a formal charge.
And the base is
going to form a bond
with that proton like that.
So this is an acid
base reaction.
So if we react an alcohol
with a strong base--
so this is a strong
base here-- we're
going to form the conjugate
base to an alcohol, which
is called an alkoxide.
So this is an alkoxide
ion right here.
So a chemical
property of alcohols,
they are acidic if you
use a strong enough base.
And the conjugate base to an
alcohol is called an alkoxide.
Let's look at an example.
So let's take ethanol.
So here I have my
ethanol molecule,
and we'll react that
with a strong base,
something like sodium
hydride, so NaH.
So Na plus, and H with 2.
Hydrogen with two electrons
around it, which makes it a
negatively charged ion.
So that's called
the hydride anion.
So we have the basic portion,
the negatively charged
hydrogen.
It's going to
function as a base.
It's going to take
these two electrons.
It's going to take that
proton right there.
So the acidic proton on alcohols
is the one on the oxygen.
And the electrons
in here are going
to kick off onto our
oxygen like that.
So we're going to
get for our product
an alkoxide with three lone
pairs of electrons around it,
giving it a negative
1 formal charge.
The sodium is floating
around, positively charged.
So it's going to
electrostatically, ionically
interact with our
alkoxide anion.
And the hydride anion
picked up a proton.
So those two hydrogens combine
to form hydrogen gas, which
will, of course, bubble
out of your solution.
So the formation of
hydrogen gas will
be observed in this reaction.
And this is how you
form an alkoxide.
This molecule is
called sodium ethoxide.
So we have sodium
ethoxide over here
on the right, sodium
ethoxide, which
is a relatively
strong base that is
used in a lot of organic
chemistry reactions.
And let's see, we used a
strong base to form it.
We used sodium hydride over
here to form that molecule
from ethanol.
So there's another
way to form alkoxides.
So let's take a look
at a generic way
to form alkoxides from
group 1 alkali metals.
So here we have our
alcohol, like that.
And if we react our alcohol
with a group 1 metal, so
an alkali metal.
Those all have one valence
electron, being in group 1
on the periodic table.
So something like lithium
or sodium or potassium.
We're going to form an alkoxide.
So we're going to
form, let's see,
three lone pairs of electrons,
a negative 1 formal charge.
In the mechanism, the metal is
going to donate its one valence
electron, leaving it
with a plus 1 charge.
So it's going to interact
with your alkoxide, like that.
And this also releases
hydrogen gas, like that.
So that's your general reaction.
Let's look at an example,
where we react cyclohexanol.
So we're going to react
cyclohexanol with sodium.
So actually, let's
go ahead and redraw
that cyclohexanol
molecule here, because I
want to show a little
bit of the mechanism.
So let's go ahead and
draw it like that,
and put our lone pairs of
electrons on the oxygen.
So sodium metal has one
valence electron like that.
So if we think
about what happens,
sodium will donate its one
valence electron very easily,
because it will then
have the stable electron
configuration of a noble gas.
So the first step
in the mechanism
is donation of this
one valence electron.
So we're going to show the
movement of one electron.
So we're going to use
a half-headed arrow.
And then the two electrons
in the bottom between oxygen
and hydrogen, we're going
to use a two-headed arrow
to show the movement of
those two electrons off
onto that oxygen.
So let's go ahead and
draw what we have now.
We have our cyclohexane
ring, and we now
have three lone
pairs of electrons
around my oxygen, which
makes it negatively charged.
And the sodium donated
its one valence electron,
so now it has a plus 1 charge.
So it's going to interact with
that negatively charged oxygen.
And what happened
to the hydrogen?
That hydrogen there is going
to pick up one electron.
So now we have hydrogen
with one electron around it.
That is extremely reactive.
Hydrogen prefers to have
two electrons around it.
So when two of those hydrogen
atoms get close to each other,
they're going to, of course,
react and share their electrons
to form hydrogen gas.
So I could draw it like that.
So that's where those
two electrons are.
The two electrons are here.
So one from one hydrogen,
one from the other hydrogen.
So hydrogen gas is going to
be produced in this reaction,
as well.
So that's an overview
of physical properties,
and also the preparation
of alkoxide anions.
properties of alcohols.
And so we're going to
compare, in this case,
alcohols to alkanes And this
alkane on the left here,
two carbons, so this
is of course ethane.
On the right, if we take
off one of those hydrogens
and replace it with an OH, we of
course have ethanol right here.
So let's start with
the boiling point.
So the boiling point of ethane
is approximately negative 89
degrees Celsius.
And since room temperature
is somewhere around 20 to 25
degrees Celsius,
at room temperature
we are much higher than the
boiling point of ethane,
which means it's already boiled.
It's already turned into a gas.
So at room temperature and
room pressure, ethane is a gas.
Ethanol, however, has a
much higher boiling point,
somewhere around
78 degrees Celsius.
And once again, since
room temperature
is somewhere around 20 to 25,
the boiling point of ethanol
is much higher than
room temperature.
So at room temperature and
pressure ethanol is a liquid.
It hasn't boiled yet.
And these large differences
in boiling points
between these two
molecules can be attributed
to the intermolecular
forces that are present.
So if two molecules of
ethane are interacting,
really the only
intermolecular force
that's holding those
molecules together
would be London
dispersion forces,
which are the weakest of
the intermolecular forces.
So it's relatively easy to
pull part two ethane molecules.
And that accounts for the
very low boiling point.
Doesn't take a lot of
energy to pull them apart.
So it's easy for it
to turn into a gas.
Ethanol, however, has a
much higher boiling point,
which means it's much harder
to pull those molecules apart.
It takes more energy.
So let's look at why ethanol
has such a higher boiling point.
So if I show two ethanol
molecules interacting,
so here is one ethanol
molecule, and let's go ahead
and draw another ethanol
molecule right here.
And if I think about the
oxygen hydrogen bond,
I know that's a
polarized covalent bond.
I know that there's a large
difference in electronegativity
between the oxygen
and the hydrogen.
Oxygen's much more
electronegative,
which means the electrons
in the bond between oxygen
and hydrogen are going to be
much closer to the oxygen atom,
giving the oxygen atom a
partial negative charge.
So these electrons in this bond
between oxygen and hydrogen
are going to move away
from the hydrogens.
And hydrogen is going to lose a
little bit of electron density,
leaving it relatively positive.
So we give it a partial
positive charge.
It's the same thing for the
other ethanol molecule, right?
Partially negative
oxygen, partially positive
hydrogen, and we know that
opposite charges attract.
So the partially
positive hydrogen
is attracted to the
partially negative oxygen.
And so there's a strong
intermolecular force
that holds those two
molecules together.
And that, of course,
is hydrogen bonding.
So there's hydrogen bonding
between alcohol molecules.
And since hydrogen bonding's the
strongest intermolecular force,
it's relatively difficult to
pull those molecules apart.
It takes a lot of energy,
takes a lot of heat,
and that's why the
boiling point of ethanol
is so much higher than the
boiling point of ethane,
and it also accounts
for the state of matter.
What about solubility?
So is ethanol soluble in water?
And of course, it is.
And the reason why is
hydrogen bonding, once again.
So if we draw a water
molecule in here,
I know that the water molecule
is polarized in the same way
that the alcohol molecule is.
So the hydrogen is
partially positive,
and the oxygen right over
here is partially negative.
And so once again,
opposite charges attract.
The hydrogen is attracted
to this oxygen here.
And so because of
hydrogen bonding,
there's interaction
between the water molecule
and in between the
alcohol molecules.
So the water molecule is polar.
So if you want to think about
it in terms of polarity,
because of the difference
in electronegativity,
water is a polar molecule,
ethanol is a polar molecule,
and like dissolves like.
So these two molecules will
be soluble in each other.
So if I look at the
structure of ethanol,
the reason why it
is soluble in water
is because of this
portion of the molecule,
this hydroxyl group, this OH.
It's the differences
in electronegativity
that allow the hydrogen bonding.
So this portion of the
molecule is the polar portion
of the molecule.
And this portion of the
molecule is the part
that loves water, which
is why it is soluble.
So if it loves water, we say
it's hydrophilic, hydro meaning
water, phil meaning
love, so hydrophilic.
Whereas this portion
over here on the left,
this is more of an alkane
type of environment,
a non-polar type of environment.
So this part of the
molecule is scared of water.
So it's hydrophobic.
So we have the hydrophobic
portion of our alcohol
molecule, and we have
the hydrophilic portion
of the alcohol molecule.
Now, we know that
like dissolves like,
so non-polar will not
dissolve in polar.
But as long as we have a
relatively small number
of carbon atoms in
our alkyl group,
the OH group is polar
enough for the alcohol
to be soluble in water.
Now, if you have a large
number of carbon atoms,
your molecule is more
non-polar than polar.
And so alcohols will stop
being soluble in water
if they have a lot of
carbon atoms on them.
So let's look at now the
preparation of alkoxides.
So let's look at an alcohol.
So here we have our alcohol.
And if we react our alcohol
with a strong base--
So we'll give it a lone pair
of electrons, a negative 1
formal charge, so we
have a strong base here.
And our strong base is
going to take this proton
and leave these electrons
behind on this oxygen.
So now we have an
oxygen that used
to have two lone
pairs of electrons
and now has three lone pairs.
That gives it a negative
1 a formal charge.
And the base is
going to form a bond
with that proton like that.
So this is an acid
base reaction.
So if we react an alcohol
with a strong base--
so this is a strong
base here-- we're
going to form the conjugate
base to an alcohol, which
is called an alkoxide.
So this is an alkoxide
ion right here.
So a chemical
property of alcohols,
they are acidic if you
use a strong enough base.
And the conjugate base to an
alcohol is called an alkoxide.
Let's look at an example.
So let's take ethanol.
So here I have my
ethanol molecule,
and we'll react that
with a strong base,
something like sodium
hydride, so NaH.
So Na plus, and H with 2.
Hydrogen with two electrons
around it, which makes it a
negatively charged ion.
So that's called
the hydride anion.
So we have the basic portion,
the negatively charged
hydrogen.
It's going to
function as a base.
It's going to take
these two electrons.
It's going to take that
proton right there.
So the acidic proton on alcohols
is the one on the oxygen.
And the electrons
in here are going
to kick off onto our
oxygen like that.
So we're going to
get for our product
an alkoxide with three lone
pairs of electrons around it,
giving it a negative
1 formal charge.
The sodium is floating
around, positively charged.
So it's going to
electrostatically, ionically
interact with our
alkoxide anion.
And the hydride anion
picked up a proton.
So those two hydrogens combine
to form hydrogen gas, which
will, of course, bubble
out of your solution.
So the formation of
hydrogen gas will
be observed in this reaction.
And this is how you
form an alkoxide.
This molecule is
called sodium ethoxide.
So we have sodium
ethoxide over here
on the right, sodium
ethoxide, which
is a relatively
strong base that is
used in a lot of organic
chemistry reactions.
And let's see, we used a
strong base to form it.
We used sodium hydride over
here to form that molecule
from ethanol.
So there's another
way to form alkoxides.
So let's take a look
at a generic way
to form alkoxides from
group 1 alkali metals.
So here we have our
alcohol, like that.
And if we react our alcohol
with a group 1 metal, so
an alkali metal.
Those all have one valence
electron, being in group 1
on the periodic table.
So something like lithium
or sodium or potassium.
We're going to form an alkoxide.
So we're going to
form, let's see,
three lone pairs of electrons,
a negative 1 formal charge.
In the mechanism, the metal is
going to donate its one valence
electron, leaving it
with a plus 1 charge.
So it's going to interact
with your alkoxide, like that.
And this also releases
hydrogen gas, like that.
So that's your general reaction.
Let's look at an example,
where we react cyclohexanol.
So we're going to react
cyclohexanol with sodium.
So actually, let's
go ahead and redraw
that cyclohexanol
molecule here, because I
want to show a little
bit of the mechanism.
So let's go ahead and
draw it like that,
and put our lone pairs of
electrons on the oxygen.
So sodium metal has one
valence electron like that.
So if we think
about what happens,
sodium will donate its one
valence electron very easily,
because it will then
have the stable electron
configuration of a noble gas.
So the first step
in the mechanism
is donation of this
one valence electron.
So we're going to show the
movement of one electron.
So we're going to use
a half-headed arrow.
And then the two electrons
in the bottom between oxygen
and hydrogen, we're going
to use a two-headed arrow
to show the movement of
those two electrons off
onto that oxygen.
So let's go ahead and
draw what we have now.
We have our cyclohexane
ring, and we now
have three lone
pairs of electrons
around my oxygen, which
makes it negatively charged.
And the sodium donated
its one valence electron,
so now it has a plus 1 charge.
So it's going to interact with
that negatively charged oxygen.
And what happened
to the hydrogen?
That hydrogen there is going
to pick up one electron.
So now we have hydrogen
with one electron around it.
That is extremely reactive.
Hydrogen prefers to have
two electrons around it.
So when two of those hydrogen
atoms get close to each other,
they're going to, of course,
react and share their electrons
to form hydrogen gas.
So I could draw it like that.
So that's where those
two electrons are.
The two electrons are here.
So one from one hydrogen,
one from the other hydrogen.
So hydrogen gas is going to
be produced in this reaction,
as well.
So that's an overview
of physical properties,
and also the preparation
of alkoxide anions.
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