THE DEHYDRATION OF ETHANOL The alternative mechanism avoids the formation of the

carbocation, and so avoids the high activation energy.

This page looks at the mechanism for the acid catalysed
dehydration of a simple primary alcohol like ethanol to give
an alkene like ethene.
This isn't as straightforward as the dehydration of a secondary
or tertiary alcohol, and it is important that you read the page
about thedehydration of propan-2-ol before you continue with
this page.
We are going to discuss the mechanism using sulphuric acid.
In the first stage, one of the lone pairs of electrons on the
oxygen picks up a hydrogen ion from the sulphuric acid. The
alcohol is said to be protonated. That is exactly the same as
happens with propan-2-ol and the other secondary and tertiary
alcohols.

The dehydration of ethanol

The facts

Ethanol can be dehydrated to give ethene by heating it with an

excess of concentrated sulphuric acid at about 170°C.

Concentrated phosphoric(V) acid, H3PO4, can be used instead.

In the mechanism we have already looked at with propan-2-ol,

the next thing to happen was loss of water to form a
carbocation, followed by removal of a hydrogen ion from the
The acids aren't written into the equation because they serve as
carbocation and the formation of a double bond.
catalysts. If you like, you could write, for example, "conc
H2SO4" over the top of the arrow.
In this case, instead of happening in two separate steps, this all
happens at the same time in one smooth operation. By doing
The mechanism that, you avoid the formation of an unstable primary
carbocation.
A problem!

You will find two versions of the mechanism for the

dehydration of primary alcohols on the web and in various
textbooks.

One of these is exactly the same as the mechanism for the

reaction involving propan-2-ol and other secondary or tertiary
alcohols (known technically as an E1 mechanism), but the
other is different (known as an E2 mechanism).
Baeyer Test for Unsaturation
The more reliable sources give the E2 mechanism for the
dehydration of primary alcohols including ethanol. I am going The Baeyer reagent is a cold dilute aqueous solution of
to treat this as the "correct" version.
potassium permanganate which is a deep purple color.
The correct version in full Potassium permanganate does not react with alkanes because
they are saturated (single bonds which are all taken). When it
If you have read the page on the dehydration of propan-2-ol,
you will know that it involves the formation of a carbocation is added to alkanes the purple color does not change.
(a carbonium ion). However, when it is added to an alkene, the purple color

If ethanol used the same mechanism, you would get a primary
carbocation formed, CH3CH2+, but this is much less stable than
a secondary or tertiary carbocation.
That would lead to a very high activation energy for the
reaction.
slowly disappears and a brown MnO2 precipitate forms. The
appearance of the brown precipitate indicates a positive
test for unsaturation. The Baeyer test for unsaturation is used
when the color of the organic compound may interfere with
the result of the Bromine Test for Unsaturation.

Purple color dilutes to light purple = SATURATED.
Purple color disappears and brown ppt forms =
UNSATURATED.
Bromine Test for Hydrocarbon Reactivity
The bromine test is used to determine if the colorless organic
compound contains any double C=C bonds (the alkene
functional group). Bromine does not react with an alkane
because the alkane contains only single C-C bonds which
cannot add the bromine. Alkanes merely dilute the red-brown
bromine color to an orange or yellow color in the absence of a
strong catalyst.
Due to their C=C double bonds which can be broken, alkenes
react readily with bromine to produce saturated
dibromoalkanes. When an alkene is reacted with bromine, the
red-brown color of the bromine is immediately lost due to the
reaction of the bromine.
Alkane + bromine (No strong light or heat) results in
diluted solution colored orange or yellow indicating no
reaction.
Alkane + bromine (heat or strong light acting as a catalyst)
results in the brown red color of bromine slowly
disappearing.
Alkene + bromine results in the red brown color of
bromine rapidly or immediately disappearing giving a
colorless solution
Aromatic hydrocarbon + bromine (no heat or light acting
as a catalyst) results in no reaction and the red brown
color of bromine is diluted to orange or yellow.
Aromatic hydrocarbons are too stable to react without a
catalyst so they act like alkanes.
If an alkene is present, the π bond breaks and bromine is
added in two places.
 The gas burns with a luminous flame.
 The adding limewater to the test-tube
Red brown color of bromine slowly disappears =
unsaturated.
Red brown color of bromine dilutes to yellow or orange =
saturated.
Bromine test for Unsaturation
Again bromine is used to determine whether an alkane, alkene,
or aromatic hydrocarbon is present. If the substance is an
alkene it will react with the bromine, indicating the compound
is unsaturated. When the red-brown color of bromine
disappears it indicates the substance is unsaturated and a
reaction has occurred.
ALKANES contain only σ (single C-C) bonds and cannot
add any Br so red brown color of bromine dilutes to yellow
or orange = saturated.
ALKENES contains a π bond making it possible to add Br
so the red brown color of bromine disappears rapidly or
immediately = unsaturated
Ethene is the formal IUPAC name for H2C=CH2, but it also
goes by a common name: Ethylene. The name Ethylene is
used because it is like an ethyl group (CH2CH3) but there is a
double bond between the two carbon atoms in it. Ethene has
the formula C2H4 and is the simplest alkene because it has the
fewest carbons (two) necessary for a carbon-carbon double
bond. It is a colorless gas at room temperature with a slightly
sweet smell. Ethene is flammable. The reactive side of an
ethene is the double bond.
RESULTS AND DISCUSSIONS
The reason why we used sulfuric acid in the experiment is that
it serves as an acid catalyst. Acid catalysts that are normally
used in these kind of experiment are phosphoric acid and, of
course, sulfuric acid. Even though concentrated sulfuric acid
produces messy results, it is the one referred in the experiment
procedures. Not only is it an acid, but it is also a strong
oxidizing agent. It oxidizes some of the alcohol to carbon
dioxide and at the same time reduces itself to form sulfur
dioxide. Both of these gases have to be removed from the
alkene. However, we still managed to obtain ethene gases.
Combustion Test
turns limewater milky. This shows that carbon dioxide was
formed when ethene burns in air.
 Addition of Bromine Test

 Bromine water turns from yellow/red colour

to colourless.
 The decolorisation of bromine is the standart test
for unsaturation in a compound.

Addition of Acidified Potassium Permanganate Note: This type of equation is quite commonly used in
organic chemistry. Oxygen written in square brackets is taken
(KMnO4) Test to mean "oxygen from an oxidising agent". The reason for this
is that a more normal equation tends to obscure the organic
change in a mass of other detail - as you will find below!
 Purple colour to colourless.
 This is also used to test for presence of a C=C double The full equations are given below, although you probably
bond (unsaturation). won't need them.
Read more on StudyNotes.ie : http://studynotes.ie/leaving-
cert/chemistry/experiment-to-prepare-ethene-and-examine-its-
properties/#ixzz2fDAaUFfz

ALKENES and POTASSIUM MANGANATE(VII)

The full equation depends on the conditions.
This page looks at the reaction of the carbon-carbon double
bond in alkenes such as ethene with potassium Under acidic conditions, the manganate(VII) ions are reduced
manganate(VII) solution (potassium permanganate solution). to manganese(II) ions.

Oxidation of alkenes with cold dilute potassium

manganate(VII) solution

Experimental details

Alkenes react with potassium manganate(VII) solution in the

cold. The colour change depends on whether the potassium
manganate(VII) is used under acidic or alkaline conditions. THE REACTION BETWEEN SYMMETRICAL
ALKENES AND BROMINE
If the potassium manganate(VII) solution is acidified with
dilute sulphuric acid, the purple solution becomes colourless.

If the potassium manganate(VII) solution is made slightly
alkaline (often by adding sodium carbonate solution), the
purple solution first becomes dark green and then produces a
dark brown precipitate.
Chemistry of the reaction
We'll look at the reaction with ethene. Other alkenes react in
just the same way.
Manganate(VII) ions are a strong oxidising agent, and in the
first instance oxidise ethene to ethane-1,2-diol (old name:
ethylene glycol).
Looking at the equation purely from the point of view of the
organic reaction:
This page gives you the facts and a simple, uncluttered
mechanism for the electrophilic addition reactions between
bromine (and the other halogens) and alkenes like ethene and
cyclohexene. If you want the mechanisms explained to you in
detail, there is a link at the bottom of the page.
The electrophilic addition of bromine to ethene
The facts
Alkenes react in the cold with pure liquid bromine, or with a
solution of bromine in an organic solvent like
tetrachloromethane. The double bond breaks, and a bromine
atom becomes attached to each carbon. The bromine loses its
original red-brown colour to give a colourless liquid. In the
case of the reaction with ethene, 1,2-dibromoethane is formed.
This decolourisation of bromine is often used as a test for a
carbon-carbon double bond. If an aqueous solution of bromine
is used ("bromine water"), you get a mixture of products. The
presence of the water complicates the mechanism beyond
what is required by current UK A level (or equivalent)
syllabuses.
The mechanism for the reaction between ethene and
bromine
The reaction is an example of electrophilic addition.
Bromine as an electrophile
The bromine is a very "polarisable" molecule and the
approaching pi bond in the ethene induces a dipole in the
bromine molecule. If you draw this mechanism in an exam,
write the words "induced dipole" next to the bromine molecule
- to show that you understand what's going on.
The simplified version of the mechanism
The more accurate version of the mechanism
In the first stage of the reaction, one of the bromine atoms
becomes attached to both carbon atoms, with the positive
charge being found on the bromine atom. A bromonium ion is
formed.
The bromonium ion is then attacked from the back by a
bromide ion formed in a nearby reaction.
Combustion
All hydrocarbons will burn in the presence of oxygen (in the
air). This reaction is
called combustion, and the products of this reaction are water
and carbon dioxide gas.
Alkenes and alkynes are much more reactive than alkanes.
They will react readily with Br2 or Cl2, and ultraviolet light is
not needed for the reaction. This reaction is an addition
reaction – the halogen atoms will add at the site of the double
bond only.
Oxidation
Another reaction that alkenes undergo is oxidation. When a
purple solution of the oxidizing agent KMnO4 is added to an
alkene, the alkene is oxidized to a diol and the KMnO4 is
converted to brown MnO2. Thus, if the purple color changes
to brown in this reaction, it is a positive reaction.
http://www.laney.edu/wp/cheli-
fossum/files/2012/01/5-Reactions-of-Hydrocarbons.pdf
 Why does the liquid become darker?
 Sulphuric acid is an oxidising agent, and removes not
only water from ethanol but also hydrogen, leaving
the carbon behind. This charring is unavoidable. The
sulphuric acid is reduced to sulphur dioxide.
What is the color of Methane gas, acetylene gas, and
Ethylene gas flame?
The flames color differ in temperature. the hotter the flame the
bluer and whiter they are. the cooler the flame the more
yellowish. so it really depends on that particular flames
temperature.
Clean blue flame