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Triiodomethane (Iodoform) Reaction With Alcohols

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18 views1 page

Triiodomethane (Iodoform) Reaction With Alcohols

Uploaded by

李忠明
Copyright
© © All Rights Reserved
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THE TRIIODOMETHANE (IODOFORM)

REACTION WITH ALCOHOLS

This page looks at how the triiodomethane (iodoform) reaction


can be used to identify the presence of a CH3CH(OH) group in
alcohols.

Note: This reaction can also be used in testing for the


CH3CO group in aldehydes and ketones. You will find a link
to this at the bottom of the page.

Doing the triiodomethane (iodoform) reaction

There are two apparently quite different mixtures of reagents


that can be used to do this reaction. They are, in fact, chemically
equivalent.

Note: It would be silly to learn both of these methods. Use


whichever one your examiners want - find out by looking at
past papers and mark schemes. If you haven't got these, go
to the syllabuses page to find out how to get hold of them.

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

Using iodine and sodium hydroxide solution

This is chemically the more obvious method.

Iodine solution is added to a small amount of an alcohol,


followed by just enough sodium hydroxide solution to remove
the colour of the iodine. If nothing happens in the cold, it may be
necessary to warm the mixture very gently.

A positive result is the appearance of a very pale yellow


precipitate of triiodomethane (previously known as iodoform) -
CHI3.

Apart from its colour, this can be recognised by its faintly


"medical" smell. It is used as an antiseptic on the sort of sticky
plasters you put on minor cuts, for example.

Using potassium iodide and sodium chlorate(I) solutions

Sodium chlorate(I) is also known as sodium hypochlorite.

Potassium iodide solution is added to a small amount of an


alcohol, followed by sodium chlorate(I) solution. Again, if no
precipitate is formed in the cold, it may be necessary to warm
the mixture very gently.

The positive result is the same pale yellow precipitate as before.

Why the two reactions are equivalent: This reaction


happens in three stages. In the first, the alcohol is oxidised to
an aldehyde or ketone. In the first mixture, the iodine reacts
with the sodium hydroxide solution to produce some sodium
iodate(I). This is an oxidising agent.

In the second mixture, the sodium chlorate(I) already present


is an oxidising agent.

After that the reaction happens in two further stages: first the
aldehyde or ketone formed reacts with iodine, and the
product of that reaction reacts with hydroxide ions. Iodine and
sodium hydroxide is exactly what you are adding in the first
method above.

In the second method, the sodium chlorate(I) solution is an


oxidising agent, and oxidises the iodide ions in the potassium
iodide to iodine. As well as any possible precipitate, you will
also see the typical reddish-brown colour of iodine solution
being formed during the reaction.

So although you didn't put any iodine into the mixture, it is


made in situ. What about the hydroxide ions?

Sodium chlorate(I) solution is alkaline and contains enough


hydroxide ions to carry out the second half of the reaction.
Sodium chlorate(I) is alkaline because it reacts reversibly with
water to form the weak acid chloric(I) acid together with
hydroxide ions.

The chemistry of the triiodomethane (iodoform)


reaction

What the triiodomethane (iodoform) reaction shows

A positive result - the pale yellow precipitate of triiodomethane


(iodoform) - is given by an alcohol containing the grouping:

"R" can be a hydrogen atom or a hydrocarbon group (for


example, an alkyl group).

If "R" is hydrogen, then you have the primary alcohol ethanol,


CH3CH2OH.

Ethanol is the only primary alcohol to give the


triiodomethane (iodoform) reaction.

If "R" is a hydrocarbon group, then you have a secondary


alcohol. Lots of secondary alcohols give this reaction, but
those that do all have a methyl group attached to the
carbon with the -OH group.

No tertiary alcohols can contain this group because no


tertiary alcohols can have a hydrogen atom attached to the
carbon with the -OH group. No tertiary alcohols give the
triiodomethane (iodoform) reaction.

Summary of the reactions during the triiodomethane


(iodoform) reaction

We will take the reagents as being iodine and sodium hydroxide


solution.

This is being given as a flow scheme rather than full equations.


You aren't likely to need the equation for the oxidation stage for
UK A level purposes. The equations for the other two steps are
given on a page about reactions of aldehydes and ketones.
Follow the first link below if you are interested.

Questions to test your understanding

If this is the first set of questions you have done, please read the
introductory page before you start. You will need to use the BACK BUTTON
on your browser to come back here afterwards.

questions on the iodoform reaction

answers

Where would you like to go now?

Using the same reaction with aldehydes and ketones .


..

To the alcohols menu . . .

To the menu of other organic compounds . . .

To Main Menu . . .

© Jim Clark 2004 (modified November 2015)

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