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BONDING IN ETHYNE (ACETYLENE)
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Important! The approach on this page follows on from the

similar (but very slightly easier) explanation of the bonding in
ethene. Unless you are already familiar with this, you should
first read the page about ethene.

To understand ethene you also have to understand orbitals

and the bonding in methane - sorry, there are no short-cuts!
Depending on how many other pages you might have to refer
to as well, return here later using the BACK button on your
browser or the GO menu or HISTORY file - or via the Organic
Bonding Menu (link from the bottom of each page in this
section).

Ethyne, C2H2

The simple view of the bonding in ethyne

Ethyne has a triple bond between the two carbon atoms. In the
diagram each line represents one pair of shared electrons.

If you have read the ethene page, you will expect that ethyne is
going to be more complicated than this simple structure suggests.

An orbital view of the bonding in ethyne

Ethyne is built from hydrogen atoms (1s1) and carbon atoms

(1s22s22px12py1).

The carbon atom doesn't have enough unpaired electrons to form

four bonds (1 to the hydrogen and three to the other carbon), so it
needs to promote one of the 2s2 pair into the empty 2pz orbital.
This is exactly the same as happens whenever carbon forms
bonds - whatever else it ends up joined to.

Important! If this isn't really clear to you, you must go and

chemguide.co.uk/basicorg/…/ethyne.html 1/4
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read the article about the bonding in methane.
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Each carbon is only joining to two other atoms rather than four (as
in methane or ethane) or three (as in ethene) and so when the
carbon atoms hybridise their outer orbitals before forming bonds,
this time they only hybridise two of the orbitals.

They use the 2s electron and one of the 2p electrons, but leave the
other 2p electrons unchanged. The new hybrid orbitals formed are
called sp1 hybrids (sometimes just sp hybrids), because they are
made by an s orbital and a single p orbital reorganising
themselves.

What these look like in the atom (using the same colour coding) is:

Notice that the two green lobes are two different hybrid orbitals -
arranged as far apart from each other as possible. Don't confuse
them with the shape of a p orbital.

The two carbon atoms and two hydrogen atoms would look like
this before they joined together:

The various atomic orbitals which are pointing towards each other
now merge to give molecular orbitals, each containing a bonding
pair of electrons. These are sigma bonds - just like those formed
by end-to-end overlap of atomic orbitals in, say, ethane. The sigma
bonds are shown as orange in the next diagram.
chemguide.co.uk/basicorg/…/ethyne.html 2/4
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The various p orbitals (now shown in slightly different reds to avoid
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confusion) are now close enough together that they overlap w
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sideways.

Sideways overlap between the two sets of p orbitals produces two

pi bonds - each similar to the pi bond found in, say, ethene. These
pi bonds are at 90° to each other - one above and below the
molecule, and the other in front of and behind the molecule. Notice
the different shades of red for the two different pi bonds.

Note: Forgive my artistic (in)ability! In particular, these

diagrams are not to scale. To get the p orbitals to overlap and
still see what is going on at the back of the molecule, you
have to shorten the carbon-carbon distance completely out of
proportion. In truth, the carbon-hydrogen bond length is
shorter than the carbon-carbon triple bond.

Where would you like to go now?

To the organic bonding menu. . .

To menu of basic organic chemistry. . .

chemguide.co.uk/basicorg/…/ethyne.html 3/4
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© Jim Clark 2006

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