Alkenes

A. Alkenes: Nomenclature

Alkenes are normally named using the IUPAC system. The rules for alkenes are similar to those used for
alkanes. The following rules summarize alkene nomenclature.

1. Identify the longest continuous chain of carbon atoms that contains the carboncarbon double
bond. The parent name of the alkene comes from the IUPAC name for the alkane with
the same number of carbon atoms, except the ane ending is changed to ene to signify the
presence of a double bond. For example, if the longest continuous chain of carbon atoms containing a
double bond has five carbon atoms, the compound is a pentene.

2. Number the carbon atoms of the longest continuous chain, starting at the end closest to the
double bond. Thus, is numbered from right to left, placing the double bond between the second and
third carbon atoms of the chain. (Numbering the chain from left to right incorrectly places the double
bond between the third and fourth carbons of the chain.)

3. The position of the double bond is indicated by placing the lower of the pair of numbers assigned to
the doublebonded carbon atoms in front of the name of the alkene. Thus, the compound shown in
rule 2 is 2pentene.

4. The location and name of any substituent molecule or group is indicated. For example, is 5chloro
2` hexene.

5. Finally, if the correct threedimensional relationship is known about the groups attached to the
double bonded carbons, the cis or trans conformation label may be assigned. Thus, the complete name
of the compound in rule 4 (shown differently here) is cis5chloro2hexene.

B. Alkenes: Physical Properties

The physical properties of alkenes are very similar to those of alkanes. Alkenes also exist as gases,
liquids, and solids at room temperature. Isomeric alkenes tend to have similar boiling points, which
makes it difficult to separate them by boiling point differences.
Substituted alkenes show small dipole moments due to small electron distribution differences. These
small differences allow cis and trans isomers to be distinguished from each other. The effects of
substitution must be deduced for each molecule, based on the positions and the electronegativity of the
atoms or groups attached to the carboncarbon double bond. Thus, in the case of cis and trans2
butene, the cis isomer shows a dipole moment of 0.33 debye units (D), while the trans isomer shows a
dipole moment of 0 D, due to cancellation of the electronic effects.

C. Sources
The natural sources of alkenes are natural gas and peteroleum.Well the olefin i.e alkene is derived from
dutch name of ethylene'olefiant gas' (oil forming gas) which refers to oily nature of product

D. Uses

Alkenes are extremely important in the manufacture of plastics. All plastics are in some way related to
alkenes. The names of some plastics (Polythene or Poly Ethene, Polypropene), relate to their alkene
partners. Plastics are used for all kinds of tasks, from packaging and wrapping, to clothing and outdoor
apparel.

Lower alkenes are used as fuel and illuminant. These may be obtained by the cracking of kerosene or
petrol.

For the manufacture of a wide variety of polymers, e.g., polyethene, polyvinylchloride (PVC) and teflon
etc.

As raw materials for the manufacture of industrial Chemicals such as alcohols, aldehydes, and etc.

Besides, alkenes also used for artificial ripening of fruits, as a general anesthetic, for making poisonous
mustard gas (War gas) and ethylene-oxygen flame.

E. Alkenes: Preparations

Alkenes are generally prepared through elimination reactions, in which two atoms on adjacent carbon
atoms are removed, resulting in the formation of a double bond.

Preparations include the dehydration of alcohols, the dehydrohalogenation of alkyl halides, and the
dehalogenation of alkanes.
Dehydration of alcohols. In dehydration reactions, a molecule of water is eliminated from an alcohol
molecule by heating the alcohol in the presence of a strong mineral acid. A double bond forms between
the adjacent carbon atoms that lost the hydrogen ion and hydroxide group.

The mechanism of this dehydration reaction consists of the following steps.

1. Protonation of the alcohol.

This step is a simple acidbase reaction, which results in the formation of an oxonium ion, a
positively charged oxygen atom.

2. Dissociation of the oxonium ion.

Dissociation of the oxonium ion produces a carbocation, which is a positively charged carbon
atom and an unstable intermediate.

3. Deprotonation of the carbocation.

The positively charged end carbon of the carbocation attracts the electrons in the overlap region
that bond it to the adjacent a carbon. This electron movement makes the carbon slightly
positive, which in turn attracts the electrons in the overlap regions of all other atoms bonded to it.
This results in the hydrogen on the carbon becoming very slightly acidic and capable of being
removed as a proton in an acidbase reaction.

Zaitsev rule. It may be possible in some instances to create a double bond through an alcohol
dehydration reaction in which hydrogen atoms are lost from two different carbons on the carbocation. The
major product is always the more highly substituted alkene, that is, the alkene with the greater number of
substituents on the carbon atoms of the double bond, an observation called the Zaitsev rule. Thus, in the
dehydration reaction of 2butanol, the following products are formed.
The Zaitsev rule predicts that the major product is 2butene. Notice that each carbon atom involved in the
double bond of 2butene has one methyl group attached to it. In the case of 1butene, one carbon atom of
the double bond has one substituent (the ethyl group), while the other carbon atom has no substituents.

Carbocation rearrangement. The carbocation in an alcohol dehydration may undergo rearrangement to

form more stable arrangements. Dehydration of 2methyl3pentanol, for example, leads to the production
of three alkenes. The mechanism for the reaction shows that the extra compound formation is due to
rearrangement of the carbocation intermediate.

The 2methyl1pentene molecule is formed via rearrangement of the intermediate carbocation.

The movement of a hydride ion (H: ) leads to the formation of a more stable carbocation. Carbocations
are classified as primary, secondary, and tertiary, as are the carbon atoms. A primary carbocation has
one alkyl group attached to it; a secondary carbocation is bonded to two alkyl groups; and a tertiary
carbocation has three alkyl groups around it.
Alkyl groups theoretically have the ability to push electrons away from themselves. This phenomenon is
called the inductive effect. The greater the number of alkyl groups pushing electrons toward a
positively charged carbon atom, the more stable the intermediate carbocation will be. This increase in
stability is due to the delocalization of charge density. A charge on an atom creates a stress on that atom.
The more the stress is spread over the molecule, the smaller the charge density becomes on any one
atom, reducing the stress. This lessening of stress makes the ion more stable. Thus, tertiary
carbocations, with three alkyl groups on which to delocalize the positive charge, are more stable than
secondary carbocations, which have only two alkyl groups on which to delocalize the positive charge. For
the same reason, secondary carbocations are more stable than primary carbocations.

In reality, alkyl groups do not push electrons away from themselves, but rather they have electrons
removed from them. When an atom picks up a positive charge and becomes an ion, its electronegativity
changes. In the original bond between two carbon atoms, the location of the overlap region relative to
each carbon atom is fixed in part by the electronegativity of the two atoms. With an increase in the
electronegativity of one of the carbon atoms due to ion formation, the overlap region shifts closer to the
more electronegative, positively charged carbon atom. This rearrangement of electron density produces a
partial positive charge on the neighboring carbon. The amount of charge gained by the second carbon
corresponds to the amount lost by the fully charged carbon atom. In this manner, the charge becomes
delocalized over the two carbons.

Dehydrohalogenation of alkyl halides. The dehydrohalogenation of alkyl halides, another

elimination reaction, involves the loss of a hydrogen and a halide from an alkyl halide (RX).
Dehydrohalogenation is normally accomplished by reacting the alkyl halide with a strong base, such as
sodium ethoxide.

This reaction also follows the Zaitsev rule, so in the reaction of 2chlorobutane with sodium ethoxide, the
major product is 2butene.

Dehydrohalogenation reactions proceed via the following mechanism.

1. A strong base removes a slightly acidic hydrogen proton from the alkyl halide via an acidbase
reaction.
 2. The electrons from the broken hydrogencarbon bond are attracted toward the slightly positive
carbon atom attached to the chlorine atom. As these electrons approach the second carbon, the halogen
atom breaks free, leading to the formation of the double bond. The diagram below summarizes this
mechanism.

Dehalogenation. Vicinal dihalides, which are alkane molecules that contain two halogen atoms on
adjacent carbon atoms, can form alkenes upon reaction with zinc.

F. Analysis

G. Reactions

THE HALOGENATION OF ALKENES

This page looks at the reaction of the carbon-carbon double bond in alkenes
such as ethene with halogens such as chlorine, bromine and iodine. This is
called halogenation.

Reactions where the chlorine or bromine are in solution (for example,

"bromine water") are slightly more complicated and are treated separately
at the end.

Simple reactions involving halogens

In each case, we will look at ethene as typical of all of the alkenes. There are
no complications as far as the basic facts are concerned as the alkenes get
bigger.

Ethene and fluorine

Ethene reacts explosively with fluorine to give carbon and hydrogen fluoride
gas. This isn't a useful reaction, and you aren't likely to need it for exam
purposes in the UK at this level (A level or equivalent).

Ethene and chlorine or bromine or iodine

In each case you get an addition reaction. For example, bromine adds to give
1,2-dibromoethane.

Note: Follow this link if you aren't happy about naming

organic compounds

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page.

The reaction with bromine happens at room temperature. If you have a

gaseous alkene like ethene, you can bubble it through either pure liquid
bromine or a solution of bromine in an organic solvent like
tetrachloromethane. The reddish-brown bromine is decolourised as it reacts
with the alkene.

A liquid alkene (like cyclohexene) can be shaken with liquid bromine or its
solution in tetrachloromethane.

Chlorine reacts faster than bromine, but the chemistry is similar. Iodine
reacts much, much more slowly, but again the chemistry is similar. You are
much more likely to meet the bromine case than either of these.

Note: If you are interested in the mechanism for the

addition of bromine to alkenes you will find it in the
mechanism section of this site.

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page.
Alkenes and bromine water

Using bromine water as a test for alkenes

If you shake an alkene with bromine water (or bubble a gaseous alkene
through bromine water), the solution becomes colourless. Alkenes
decolourise bromine water.

The chemistry of the test

This is complicated by the fact that the major product isn't 1,2-
dibromoethane. The water also gets involved in the reaction, and most of
the product is 2-bromoethanol.

However, there will still be some 1,2-dibromoethane formed, so at this sort

of level you can probably get away with quoting the simpler equation:

ALKENES and HYDROGEN HALIDES

This page looks at the reaction of the carbon-carbon double bond in alkenes
such as ethene with hydrogen halides such as hydrogen chloride and
hydrogen bromide.

Symmetrical alkenes (like ethene or but-2-ene) are dealt with first. These are
alkenes where identical groups are attached to each end of the carbon-
carbon double bond. The extra problems associated with unsymmetrical
ones like propene are covered in a separate section afterwards.

Addition to symmetrical alkenes

What happens?
All alkenes undergo addition reactions with the hydrogen halides. A
hydrogen atom joins to one of the carbon atoms originally in the double
bond, and a halogen atom to the other.

For example, with ethene and hydrogen chloride, you get chloroethane:

With but-2-ene you get 2-chlorobutane:

Note: Follow this link if you aren't happy about naming organic
compounds

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What happens if you add the hydrogen to the carbon atom at the right-hand
end of the double bond, and the chlorine to the left-hand end? You would
still have the same product.

The chlorine would be on a carbon atom next to the end of the chain - you
would simply have drawn the molecule flipped over in space.

That would be different of the alkene was unsymmetrical - that's why we

have to look at them separately.

Conditions

The alkenes react with gaseous hydrogen halides at room temperature. If

the alkene is also a gas, you can simply mix the gases. If the alkene is a
liquid, you can bubble the hydrogen halide through the liquid.

Alkenes will also react with concentrated solutions of the gases in water. A
solution of hydrogen chloride in water is, of course, hydrochloric acid. A
solution of hydrogen bromide in water is hydrobromic acid - and so on.

There are, however, problems with this. The water will also get involved in
the reaction and you end up with a mixture of products.
 Warning! The mechanism for this reaction is almost invariably given
for the reaction involving the alkene and the simple molecules H-Cl or
H-Br or whatever. In the presence of water, these molecules will
already have reacted with the water to produce hydroxonium ions,
H3O+, and halide ions. The mechanism will therefore be different -
involving an initial attack by a hydroxonium ion. Avoid this problem by
using the pure gaseous hydrogen halide.

If you choose to follow this link to the mechanism, use the BACK
button on your browser to return to this page.

Reaction rates

Variation of rates when you change the halogen

Reaction rates increase in the order HF - HCl - HBr - HI. Hydrogen fluoride
reacts much more slowly than the other three, and is normally ignored in
talking about these reactions.

When the hydrogen halides react with alkenes, the hydrogen-halogen bond
has to be broken. The bond strength falls as you go from HF to HI, and the
hydrogen-fluorine bond is particularly strong. Because it is difficult to break
the bond between the hydrogen and the fluorine, the addition of HF is
bound to be slow.

Variation of rates when you change the alkene

This applies to unsymmetrical alkenes as well as to symmetrical ones. For

simplicity the examples given below are all symmetrical ones- but they don't
have to be.

Reaction rates increase as the alkene gets more complicated - in the sense
of the number of alkyl groups (such as methyl groups) attached to the
carbon atoms at either end of the double bond.

For example:
There are two ways of looking at the reasons for this - both of which need
you to know about the mechanism for the reactions.

Note: If you should know about the mechanism, but are a bit
uncertain about it, then you should spend some time exploring
the electrophilic addition mechanisms menu before you go on, and
then come back to this page later. You should look at the addition of
hydrogen halides to unsymmetrical alkenes as well as symmetrical
ones.

This will take you some time. Use the BACK button (or, more
efficiently, the HISTORY file or GO menu) on your browser to return to
this page.

If you don't need to know about the mechanisms, skip over the next
bit!

Alkenes react because the electrons in the pi bond attract things with any
degree of positive charge. Anything which increases the electron density
around the double bond will help this.

Alkyl groups have a tendency to "push" electrons away from themselves

towards the double bond. The more alkyl groups you have, the more
negative the area around the double bonds becomes.

The more negatively charged that region becomes, the more it will attract
molecules like hydrogen chloride.

Note: If you aren't sure about pi bonds, you will find a simple mention
of them in the introductory page on alkenes

You will find more about the electron pushing effect of alkyl groups on
a page about carbocations in the mechanism section of this site. That is
also important reading if you are to understand the next bit.

Use the BACK button on your browser to return to this page later.
The more important reason, though, lies in the stability of the intermediate
ion formed during the reaction. The three examples given above produce
these carbocations (carbonium ions) at the half-way stage of the reaction:

The stability of the intermediate ions governs the activation energy for the
reaction. As you go towards the more complicated alkenes, the activation
energy for the reaction falls. That means that the reactions become faster.

Didn't understand this? You should have followed the link to the page
about carbocations mentioned above!

Use the BACK button on your browser to return to this page

afterwards.

Addition to unsymmetrical alkenes

What happens?

In terms of reaction conditions and the factors affecting the rates of the
reaction, there is no difference whatsoever between these alkenes and the
symmetrical ones described above. The problem comes with the orientation
of the addition - in other words, which way around the hydrogen and the
halogen add across the double bond.
Orientation of addition

If HCl adds to an unsymmetrical alkene like propene, there are two possible
ways it could add. However, in practice, there is only one major product.

This is in line with Markovnikov's Rule which says:

When a compound HX is added to an unsymmetrical alkene, the hydrogen

becomes attached to the carbon with the most hydrogens attached to it
already.

In this case, the hydrogen becomes attached to the CH2 group, because the
CH2 group has more hydrogens than the CH group.

Notice that only the hydrogens directly attached to the carbon atoms at
either end of the double bond count. The ones in the CH3 group are totally
irrelevant.

Warning! Markovnikov's Rule is a useful guide for you to work out

which way round to add something across a double bond, but it isn't
the reason why things add that way. As a general principle, don't quote
Markovnikov's Rule in an exam unless you are specifically asked for it.

You will find the proper reason for this in a page about the addition of
hydrogen halides to unsymmetrical alkenes in the mechanism section
of this site.

Use the BACK button on your browser if you want to return to this
page.
A special problem with hydrogen bromide

Unlike the other hydrogen halides, hydrogen bromide can add to a carbon-
carbon double bond either way around - depending on the conditions of the
reaction.

If the hydrogen bromide and alkene are entirely pure

In this case, the hydrogen bromide adds on according to Markovnikov's Rule.

For example, with propene you would get 2-bromopropane.

That is exactly the same as the way the other hydrogen halides add.

If the hydrogen bromide and alkene contain traces of organic peroxides

Oxygen from the air tends to react slowly with alkenes to produce some
organic peroxides, and so you don't necessarily have to add them
separately. This is therefore the reaction that you will tend to get unless you
take care to exclude all air from the system.

In this case, the addition is the other way around, and you get 1-
bromopropane:

This is sometimes described as an anti-Markovnikov additionor as

the peroxide effect.

Organic peroxides are excellent sources of free radicals. In the presence of

these, the hydrogen bromide reacts with alkenes using a different (faster)
mechanism. For various reasons, this doesn't happen with the other
hydrogen halides.

This reaction can also happen in this way in the presence of ultra-violet light
of the right wavelength to break the hydrogen-bromine bond into hydrogen
and bromine free radicals.

ALKENES and SULPHURIC ACID

This page looks at the reaction of the carbon-carbon double bond in
alkenes such as ethene with concentrated sulphuric acid. It includes the
conversion of the product into an alcohol.

The addition of sulphuric acid to alkenes

The reaction with ethene

Alkenes react with concentrated sulphuric acid in the cold to produce alkyl
hydrogensulphates. Ethene reacts to give ethyl hydrogensulphate.

The structure of the product molecule is sometimes written as

CH3CH2HSO4, but the version in the equation is better because it shows
how all the atoms are linked up. You may also find it written as
CH3CH2OSO3H.

Confused by all this? Don't be!

All you need to do is to learn the structure of sulphuric acid. A

hydrogen from the sulphuric acid joins on to one of the carbon
atoms, and the rest joins on to the other one. Make sure that
you can see how the structure of the sulphuric acid relates to
the various ways of writing the formula for the product.

Important! Learn this structure for sulphuric acid. Sketch it

over and over again until you can't possibly get it wrong.

Follow this link if you want the mechanism for this reaction.

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The reaction with propene

This is typical of the reaction with unsymmetrical alkenes. An unsymmetrical

alkene has different groups at either end of the carbon-carbon double bond.

If sulphuric acid adds to an unsymmetrical alkene like propene, there are

two possible ways it could add. You could end up with one of two products
depending on which carbon atom the hydrogen attaches itself to.
However, in practice, there is only one major product.

This is in line with Markovnikov's Rule which says:

When a compound HX is added to an unsymmetrical alkene, the hydrogen

becomes attached to the carbon with the most hydrogens attached to it
already.

In this case, the hydrogen becomes attached to the CH2 group, because the
CH2 group has more hydrogens than the CH group.

Notice that only the hydrogens directly attached to the carbon atoms at
either end of the double bond count. The ones in the CH3 group are totally
irrelevant.

Warning! Markovnikov's Rule is a useful guide for you to work

out which way round to add something across a double bond,
but it isn't the reason why things add that way. As a general
principle, don't quote Markovnikov's Rule in an exam unless
you are specifically asked for it.

You can find more about this in the mechanism section of this
site. You will find the mechanism for this reaction discussed in
detail if you follow this link.

Use the BACK button (or HISTORY file or GO menu, if you have
to explore several pages) on your browser if you want to return
to this page.

Using these reactions to make alcohols

Making ethanol

Ethene is passed into concentrated sulphuric acid to make ethyl

hydrogensulphate (as above). The product is diluted with water and then
distilled.
The water reacts with the ethyl hydrogensulphate to produce ethanol which
distils off.

Making propan-2-ol

More complicated alkyl hydrogensulphates react with water in exactly the

same way. For example:

Notice that the position of the -OH group is determined by where the
HSO4 group was attached. You get propan-2-ol rather than propan-1-ol
because of the way the sulphuric acid originally added across the double
bond in propene.

Using these reactions

These reactions were originally used as a way of manufacturing alcohols

from alkenes in the petrochemical industry. These days, alcohols like ethanol
or propan-2-ol tend to be manufactured by direct hydration of the alkene
because it is cheaper and easier.

ALKENES and POTASSIUM MANGANATE(VII)

This page looks at the reaction of the carbon-carbon double bond in alkenes
such as ethene with potassium manganate(VII) solution (potassium
permanganate solution).

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.

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:

Note: This type of equation is quite commonly used in organic

chemistry. Oxygen written in square brackets is taken 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!

The full equations are given below, although you probably won't
need them.

The full equation depends on the conditions.

Under acidic conditions, the manganate(VII) ions are reduced to

manganese(II) ions.

Note: If you want to know how to write equations for redox

reactions like this you could follow this link, and explore in the redox
section of this site.

Use the BACK button (or HISTORY file or GO menu) on your

browser to return to this page later.
Under alkaline conditions, the manganate(VII) ions are first
reduced to green manganate(VI) ions . . .

. . . but eventually you get dark brown solid manganese(IV)

oxide (manganese dioxide) formed. The overall equation for the
formation of this from the manganate(VII) ions is:

This last reaction is also the one you would get if the reaction
was done under neutral conditions. You will notice that there are
neither hydrogen ions nor hydroxide ions on the left-hand side of
the equation.

Note: You might possibly remember that further up the page it says
that potassium manganate(VII) is often made slightly alkaline by
adding sodium carbonate solution. Where are the hydroxide ions in
this?

Carbonate ions react with water to some extent to produce

hydrogencarbonate ions and hydroxide ions. It is the presence of
these hydroxide ions that gives sodium carbonate solution its pH in
the 10 - 11 region.

Using the reaction to test for carbon-carbon double bonds

If an organic compound reacts with dilute alkaline potassium

manganate(VII) solution in the cold to give a green solution
followed by a dark brown precipitate, then it may contain a
carbon-carbon double bond. But equally it could be any one of a
large number of other compounds all of which can be oxidised
by manganate(VII) ions under alkaline conditions.

The situation with acidified potassium manganate(VII) solution is

even worse because it has a tendency to break carbon-carbon
bonds. It reacts destructively with a large number of organic
compounds and is rarely used in organic chemistry.

You could use alkaline potassium manganate(VII) solution if, for

example, all you had to do was to find out whether a
hydrocarbon was an alkane or an alkene - in other words, if
there was nothing else present which could be oxidised.

It isn't a useful test. Bromine water is far more clear cut.

Note: You will find details of the use of bromine water in testing for
carbon-carbon double bonds in the page about the reactions of
alkenes with halogens.

Oxidation of alkenes with hot concentrated acidified

potassium manganate(VII) solution

This is where it gets complicated! Check with your syllabus to

see whether you need to know about it before you go any
further. This section was written to cover a statement in the
Cambridge International (CIE) A level syllabus.

The problem

The diols, such as ethane-1,2-diol, which are the products of the

reaction with cold dilute potassium manganate(VII), are
themselves quite easily oxidised by manganate(VII) ions. That
means that the reaction won't stop at this point unless the
potassium manganate(VII) solution is very dilute, very cold, and
preferably not under acidic conditions.

If you are using hot concentrated acidified potassium

manganate(VII) solution, what you finally end up with depends
on the arrangement of groups around the carbon-carbon double
bond.

Writing a structural formula to represent any alkene

The formula below represents a general alkene. In organic

chemistry, the symbol R is used to represent hydrocarbon
groups or hydrogen in a formula when you don't want to talk
about specific compounds. If you use the symbol more than
once in a formula (as here), the various groups are written as
R1, R2, etc.

In this particular case, the double bond is surrounded by four

such groups, and these can be any combination of same or
different - so they could be 2 hydrogens, a methyl and an ethyl,
or 1 hydrogen and 3 methyls, or 1 hydrogen and 1 methyl and 1
ethyl and 1 propyl, or any other combination you can think of.

In other words, this formula represents every possible simple

alkene:

The first stage of the extended oxidation

The acidified potassium manganate(VII) solution oxidises the

alkene by breaking the carbon-carbon double bond and
replacing it with two carbon-oxygen double bonds.

The products are known as carbonyl compounds because

they contain the carbonyl group, C=O. Carbonyl compounds can
also react with potassium manganate(VII), but how they react
depends on what is attached to the carbon-oxygen double bond.
So we need to work through all the possible combinations.

Warning: The rest of this page is going to look quite difficult,

because it talks in some detail about compounds you probably won't
 have studied yet. It may be best just to go through this quickly for
now, and then come back to it later on after you have studied
aldehydes and ketones.

What happens next?

If both attached R groups in the products are alkyl groups

Carbonyl compounds which have two hydrocarbon groups

attached to the carbonyl group are called ketones. Ketones
aren't that easy to oxidise, and so there is no further action. (But
see note in red below.)

If the groups attached either side of the original carbon-carbon

double bond were the same, then you would end up with a
single ketone. If they were different, then you would end up with
a mixture of two.

For example:

In this case, you would end up with two identical molecules

called propanone. On the other hand, if one of the methyl
groups in the original molecule was replaced by an ethyl group,
you would get a mixture of two different ketones - propanone
and butanone.

What would you get if there was a methyl and an ethyl group on
both sides of the original carbon-carbon double bond? Again,
you would get a single ketone formed - in this case, butanone. If
you aren't sure about this, draw the structures and see.

Important: This last section is a gross over-simplification for the

purposes of the CIE A level syllabus. In practice,
ketones are oxidised by potassium manganate(VII) solution under
these conditions. The reaction is untidy and results in breaking
carbon-carbon bonds either side of the carbonyl group. If you are
doing CIE, then you will have to learn this as stated above. If you are
 doing anything else, you probably shouldn't be wasting your time
reading this anyway. Potassium manganate(VII) is such a
devastating oxidising agent that it is rarely used in organic chemistry.
Check your syllabus!

If a product has one hydrocarbon group and one hydrogen

For example, suppose the first stage of the reaction was:

In this case, the first product molecule has a methyl group and a
hydrogen attached to the carbonyl group. This is a different sort
of compound known as an aldehyde.

Aldehydes are readily oxidised to give carboxylic acids,

containing the -COOH group. So this time, the reaction will go
on a further step to give ethanoic acid, CH3COOH.

The acid structure has been turned around slightly to make it

look more like the way we normally draw acids, but the net effect
is that an oxygen has been slotted in between the carbon and
hydrogen.

The overall effect of the potassium manganate(VII) on this kind

of alkene is therefore:

Obviously, if there was a hydrogen atom attached to both

carbons at the ends of the carbon-carbon double bond, you
would get two carboxylic acid molecules formed - which might
be the same or different, depending on whether the alkyl groups
were the same or different.

Play around with this until you are happy about it. Draw a
number of alkenes, all of which have a hydrogen attached at
both ends of the carbon-carbon double bond. Vary the alkyl
groups - sometimes the same on each end of the double bond,
sometimes different. Oxidise them to form the acids, and see
what you get.

If a product has two hydrogens but no hydrocarbon group

You might have expected that this would produce methanoic

acid, as in the equation:

But it doesn't! That's because methanoic acid is also easily

oxidised by potassium manganate(VII) solution. In fact, it
oxidises it all the way to carbon dioxide and water.

So the equation in a case like this might be, for example:

The exact nature of the other product (in this example,

propanone) will vary depending on what was attached to the
right-hand carbon in the carbon-carbon double bond.

If there were two hydrogens at both ends of the double bond (in
other words, if you had ethene), then all you would get would be
carbon dioxide and water.

Summary
Think about both ends of the carbon-carbon double bond
separately, and then combine the results afterwards.

If there are two alkyl groups at one end of the bond, that
part of the molecule will give a ketone.
If there is one alkyl group and one hydrogen at one end
of the bond, that part of the molecule will give a carboxylic
acid.
If there are two hydrogens at one end of the bond, that
part of the molecule will give carbon dioxide and water.

What is the point of all this?

Working back from the results helps you to work out the
structure of the alkene. For example, the alkene C4H8 has three
structural isomers:

Work out which of these would give each of the following results
if they were treated with hot concentrated potassium
manganate(VII) solution. The isomers above are not in the order
A, B and C.

Don't read the answers in the green box until you have had a go
at this.

Isomer A gives a ketone (propanone) and carbon dioxide.

Isomer B gives a carboxylic acid (propanoic acid) and
carbon dioxide.
Isomer C gives a carboxylic acid (ethanoic acid).