Lewis structure of CH2CHCN

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Lewis structure of CH2CHCN
Lewis structure of CH2CHCN | Image: Root Memory

The Lewis structure of CH2CHCN contains four single bonds, one double bond, and one triple bond, with three carbons in the center, and nitrogen and three hydrogens on either side. The left carbon is attached with two hydrogens, center carbon is attached with one hydrogen, and right carbon is attached with one nitrogen. There is one lone pair on the nitrogen atom, and carbon atom and hydrogen atom do not have any lone pair.

Steps

By using the following steps, you can easily draw the Lewis structure of CH2CHCN.

#1 Draw skeleton
#2 Show chemical bond
#3 Mark lone pairs
#4 Complete octet on atoms
#5 Calculate formal charge and check stability

Let’s one by one discuss each step in detail.

#1 Draw skeleton

In this step, first calculate the total number of valence electrons. And then, decide the central atom.

  • Let’s calculate the total number of valence electrons

We know that… carbon is a group 14 element, hydrogen is a group 1 element, and nitrogen is a group 15 element. Hence, carbon has four valence electrons, hydrogen has one valence electron, and nitrogen has five valence electrons.

Now CH2CHCN has three carbon atoms, three hydrogen atoms, and one nitrogen atom.

So the total number of valence electrons = (valence electrons of carbon atom × 3) + (valence electrons of hydrogen atom × 3) + valence electrons of nitrogen atom

Therefore, the total number of valence electrons = 12 + 3 + 5 = 20

  • Now decide the central atom

We can not assume hydrogen as the central atom, because the central atom is bonded with at least two other atoms. And hydrogen has only one electron in its last shell, so it can not make more than one bond.

Therefore, choose the central atom from carbon and nitrogen.

The atom with the least electronegative value is placed at the center. By looking at the periodic table, we get the electronegativity values for carbon and nitrogen as follows:

Electronegativity value of carbon = 2.55
Electronegativity value of nitrogen = 3.04

Obviously, carbon is less electronegative than nitrogen. Hence, assume that center carbon is the central atom (as there are three carbons).

So now, put three carbons in the center and nitrogen and three hydrogens on either side. And draw the rough skeleton structure for the Lewis structure of CH2CHCN something like this:

Skeleton structure for Lewis structure of CH2CHCN | Image: Root Memory

#2 Show chemical bond

Place two electrons between the atoms to show a chemical bond. Since three carbons are surrounded by nitrogen and three hydrogens, use twelve electrons to show six chemical bonds as follows:

Six chemical bonds shown between atoms | Image: Root Memory

#3 Mark lone pairs

As calculated earlier, we have a total of 20 valence electrons. And in the above structure, we have already used twelve valence electrons. Hence, eight valence electrons are remaining.

Two valence electrons represent one lone pair. So eight valence electrons = four lone pairs.

Note that both (carbon and nitrogen) are the period 2 elements, so they can not keep more than 8 electrons in their last shell. And hydrogen is a period 1 element, so it can not keep more than 2 electrons in its last shell.

Also, make sure that you start marking these lone pairs on outside atoms first. And then, on the central atom.

The outside atoms are hydrogens, nitrogen, left carbon, and right carbon. But hydrogen can not keep more than 2 electrons in its last shell. Hence, don’t mark the lone pairs on hydrogen.

So nitrogen will get three lone pairs, and left carbon will get one lone pair. And right carbon and central atom (left carbon) will not get any lone pair, because all four lone pairs are used.

Now draw the Lewis structure of CH2CHCN something like this:

Lone pairs marked on Lewis structure of CH2CHCN | Image: Root Memory

In the above structure, you can see that the octet is completed on outside atoms (except right carbon). Also, the central atom (center carbon) doesn’t form an octet.

So in the next step, we have to complete the octet on center carbon and right carbon.

#4 Complete octet on atoms

Remember that carbon is a period 2 element, so it can not keep more than 8 electrons in its last shell.

Now center carbon already has six valence electrons. Hence, center carbon needs two more valence electrons to complete its octet.

And right carbon already has four valence electrons. Hence, right carbon needs four more valence electrons to complete its octet.

So convert one lone pair from the left carbon atom to make a new bond with the center carbon atom, and two lone pairs from the nitrogen atom to make a new bond with the right carbon atom.

And then, the Lewis structure of CH2CHCN looks something like this:

Lone pair of left carbon and nitrogen is converted, and octet is completed on atoms | Image: Root Memory

In the above structure, you can see that the octet is completed on the central atom (center carbon), and also on the outside atoms. Therefore, the octet rule is satisfied.

After completing the octet, one last thing we need to do is, calculate the formal charge and check the stability of the above structure.

#5 Calculate formal charge and check stability

The following formula is used to calculate the formal charges on atoms:

Formal charge = valence electrons – nonbonding electrons – ½ bonding electrons

Collect the data from the above structure and then, write it down below as follows:

  • For each hydrogen atom

Valence electrons = 1
Nonbonding electrons = 0
Bonding electrons = 2

Formal charge = 1 – 0 – ½ (2) = 0

  • For each carbon atom

Valence electrons = 4
Nonbonding electrons = 0
Bonding electrons = 8

Formal charge = 4 – 0 – ½ (8) = 0

  • For nitrogen atom

Valence electrons = 5
Nonbonding electrons = 2
Bonding electrons = 6

Formal charge = 5 – 2 – ½ (6) = 0

Mention the formal charges of atoms on the structure. So the Lewis structure of CH2CHCN looks something like this:

Formal charges are calculated, and got the stable Lewis structure of CH2CHCN | Image: Root Memory

In the above structure, you can see that the formal charges of all atoms are zero. Therefore, this is the stable Lewis structure of CH2CHCN.

And each horizontal line drawn in the above structure represents a pair of bonding valence electrons.

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External links

Deep

Rootmemory.com was founded by Deep Rana, who is a mechanical engineer by profession and a blogger by passion. He has a good conceptual knowledge on different educational topics and he provides the same on this website. He loves to learn something new everyday and believes that the best utilization of free time is developing a new skill.

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