Generating the Lewis dot Structure. To generate the Lewis dot structure, you have to follow the given steps: Find the total count of valence electrons to molecules. In this step, add the total count of valence electrons from all the atoms in a bit. Find the required count of electrons needed to make the atoms complete.

The ChemDoodle Web Components library is a pure JavaScript chemical graphics and cheminformatics library derived from the ChemDoodle application and produced by iChemLabs. ChemDoodle Web Components allow the wielder to present publication quality 2D and 3D graphics and animations for chemical structures, reactions and spectra. Lewis Dot Structure. Lewis dot structures reflect the electronic structures of the elements, including how the electrons are paired. Lewis structures are a useful way to summarize certain information about bonding and may be thought of as “electron bookkeeping”. In Lewis dot structures each dot represents an electron. A pair of dots between. A step-by-step explanation of how to draw the LiF Lewis Dot Structure.For LiF we have an ionic compound and we need to take that into account when we draw th.

Lewis structures, also known as Lewis dot formulas,Lewis dot structures, electron dot structures, or Lewis electron dot structures (LEDS), are diagrams that show the bonding between atoms of a molecule and the lone pairs of electrons that may exist in the molecule.^[1][2][3] A Lewis structure can be drawn for any covalently bonded molecule, as well as coordination compounds. The Lewis structure was named after Gilbert N. Lewis, who introduced it in his 1916 article The Atom and the Molecule.^[4] Lewis structures extend the concept of the electron dot diagram by adding lines between atoms to represent shared pairs in a chemical bond.

Lewis structures show each atom and its position in the structure of the molecule using its chemical symbol. Lines are drawn between atoms that are bonded to one another (pairs of dots can be used instead of lines). Excess electrons that form lone pairs are represented as pairs of dots, and are placed next to the atoms.

Although main group elements of the second period and beyond usually react by gaining, losing, or sharing electrons until they have achieved a valence shell electron configuration with a full octet of (8) electrons, hydrogen (H) can only form bonds which share just two electrons.

Construction and electron counting[edit]

The total number of electrons represented in a Lewis structure is equal to the sum of the numbers of valence electrons on each individual atom. Non-valence electrons are not represented in Lewis structures.

Once the total number of available electrons has been determined, electrons must be placed into the structure according to these steps:

1. The atoms are first connected by single bonds.
2. If t is the total number of electrons and n the number of single bonds, t-2n electrons remain to be placed. These should be placed as lone pairs: one pair of dots for each pair of electrons available. Lone pairs should initially be placed on outer atoms (other than hydrogen) until each outer atom has eight electrons in bonding pairs and lone pairs; extra lone pairs may then be placed on the central atom. When in doubt, lone pairs should be placed on more electronegative atoms first.
3. Once all lone pairs are placed, atoms (especially the central atoms) may not have an octet of electrons. In this case, the atoms must form a double bond; a lone pair of electrons is moved to form a second bond between the two atoms. As the bonding pair is shared between the two atoms, the atom that originally had the lone pair still has an octet; the other atom now has two more electrons in its valence shell.

Lewis structures for polyatomic ions may be drawn by the same method. When counting electrons, negative ions should have extra electrons placed in their Lewis structures; positive ions should have fewer electrons than an uncharged molecule. When the Lewis structure of an ion is written, the entire structure is placed in brackets, and the charge is written as a superscript on the upper right, outside the brackets.

A simpler method has been proposed for constructing Lewis structures, eliminating the need for electron counting: the atoms are drawn showing the valence electrons; bonds are then formed by pairing up valence electrons of the atoms involved in the bond-making process, and anions and cations are formed by adding or removing electrons to/from the appropriate atoms.^[5]

A trick is to count up valence electrons, then count up the number of electrons needed to complete the octet rule (or with hydrogen just 2 electrons), then take the difference of these two numbers. The answer is the number of electrons that make up the bonds. The rest of the electrons just go to fill all the other atoms' octets.

Another simple and general procedure to write Lewis structures and resonance forms has been proposed.^[6]

Formal charge[edit]

In terms of Lewis structures, formal charge is used in the description, comparison, and assessment of likely topological and resonance structures^[7] by determining the apparent electronic charge of each atom within, based upon its electron dot structure, assuming exclusive covalency or non-polar bonding. It has uses in determining possible electron re-configuration when referring to reaction mechanisms, and often results in the same sign as the partial charge of the atom, with exceptions. In general, the formal charge of an atom can be calculated using the following formula, assuming non-standard definitions for the markup used:

${\displaystyle C_f=N_v-U_e-\frac{B_n}{2}}$

where:

• ${\displaystyle C_f}$ is the formal charge.
• ${\displaystyle N_v}$ represents the number of valence electrons in a free atom of the element.
• ${\displaystyle U_e}$ represents the number of unshared electrons on the atom.
• ${\displaystyle B_n}$ represents the total number of electrons in bonds the atom has with another.

The formal charge of an atom is computed as the difference between the number of valence electrons that a neutral atom would have and the number of electrons that belong to it in the Lewis structure. Electrons in covalent bonds are split equally between the atoms involved in the bond. The total of the formal charges on an ion should be equal to the charge on the ion, and the total of the formal charges on a neutral molecule should be equal to zero.

Resonance[edit]

For some molecules and ions, it is difficult to determine which lone pairs should be moved to form double or triple bonds, and two or more different resonance structures may be written for the same molecule or ion. In such cases it is usual to write all of them with two-way arrows in between (see Example below). This is sometimes the case when multiple atoms of the same type surround the central atom, and is especially common for polyatomic ions.

When this situation occurs, the molecule's Lewis structure is said to be a resonance structure, and the molecule exists as a resonance hybrid. Each of the different possibilities is superimposed on the others, and the molecule is considered to have a Lewis structure equivalent to some combination of these states.

The nitrate ion (NO₃⁻), for instance, must form a double bond between nitrogen and one of the oxygens to satisfy the octet rule for nitrogen. However, because the molecule is symmetrical, it does not matter which of the oxygens forms the double bond. In this case, there are three possible resonance structures. Expressing resonance when drawing Lewis structures may be done either by drawing each of the possible resonance forms and placing double-headed arrows between them or by using dashed lines to represent the partial bonds (although the latter is a good representation of the resonance hybrid which is not, formally speaking, a Lewis structure).

When comparing resonance structures for the same molecule, usually those with the fewest formal charges contribute more to the overall resonance hybrid. When formal charges are necessary, resonance structures that have negative charges on the more electronegative elements and positive charges on the less electronegative elements are favored.

Single bonds can also be moved in the same way to create resonance structures for hypervalent molecules such as sulfur hexafluoride, which is the correct description according to quantum chemical calculations instead of the common expanded octet model.

The resonance structure should not be interpreted to indicate that the molecule switches between forms, but that the molecule acts as the average of multiple forms.

Example[edit]

The formula of the nitrite ion is NO−
2.

1. Nitrogen is the least electronegative atom of the two, so it is the central atom by multiple criteria.
2. Count valence electrons. Nitrogen has 5 valence electrons; each oxygen has 6, for a total of (6 × 2) + 5 = 17. The ion has a charge of −1, which indicates an extra electron, so the total number of electrons is 18.
3. Connect the atoms by single bonds. Each oxygen must be bonded to the nitrogen, which uses four electrons—two in each bond.
4. Place lone pairs. The 14 remaining electrons should initially be placed as 7 lone pairs. Each oxygen may take a maximum of 3 lone pairs, giving each oxygen 8 electrons including the bonding pair. The seventh lone pair must be placed on the nitrogen atom.
5. Satisfy the octet rule. Both oxygen atoms currently have 8 electrons assigned to them. The nitrogen atom has only 6 electrons assigned to it. One of the lone pairs on an oxygen atom must form a double bond, but either atom will work equally well. Therefore, there is a resonance structure.
6. Tie up loose ends. Two Lewis structures must be drawn: Each structure has one of the two oxygen atoms double-bonded to the nitrogen atom. The second oxygen atom in each structure will be single-bonded to the nitrogen atom. Place brackets around each structure, and add the charge (−) to the upper right outside the brackets. Draw a double-headed arrow between the two resonance forms.

Alternative formations[edit]

Chemical structures may be written in more compact forms, particularly when showing organic molecules. In condensed structural formulas, many or even all of the covalent bonds may be left out, with subscripts indicating the number of identical groups attached to a particular atom.Another shorthand structural diagram is the skeletal formula (also known as a bond-line formula or carbon skeleton diagram). In a skeletal formula, carbon atoms are not signified by the symbol C but by the vertices of the lines. Hydrogen atoms bonded to carbon are not shown—they can be inferred by counting the number of bonds to a particular carbon atom—each carbon is assumed to have four bonds in total, so any bonds not shown are, by implication, to hydrogen atoms.

Other diagrams may be more complex than Lewis structures, showing bonds in 3D using various forms such as space-filling diagrams.

Usage and limitations[edit]

Despite their simplicity and development in the early twentieth century, when understanding of chemical bonding was still rudimentary, Lewis structures capture many of the key features of the electronic structure of a range of molecular systems, including those of relevance to chemical reactivity. Thus, they continue to enjoy widespread use by chemists and chemistry educators. This is especially true in the field of organic chemistry, where the traditional valence-bond model of bonding still dominates, and mechanisms are often understood in terms of curve-arrow notation superimposed upon skeletal formulae, which are shorthand versions of Lewis structures. Due to the greater variety of bonding schemes encountered in inorganic and organometallic chemistry, many of the molecules encountered require the use of fully delocalized molecular orbitals to adequately describe their bonding, making Lewis structures comparatively less important (although they are still common).

It is important to note that there are simple and archetypal molecular systems for which a Lewis description, at least in unmodified form, is misleading or inaccurate. Notably, the naive drawing of Lewis structures for molecules known experimentally to contain unpaired electrons (e.g., O₂, NO, and ClO₂) leads to incorrect inferences of bond orders, bond lengths, and/or magnetic properties. A simple Lewis model also does not account for the phenomenon of aromaticity. For instance, Lewis structures do not offer an explanation for why cyclic C₆H₆ (benzene) experiences special stabilization beyond normal delocalization effects, while C₄H₄ (cyclobutadiene) actually experiences a special destabilization. Molecular orbital theory provides the most straightforward explanation for these phenomena.

See also[edit]

References[edit]

1. ^IUPAC definition of Lewis formula
2. ^Zumdahl, S. (2005) Chemical Principles Houghton-Mifflin (ISBN0-618-37206-7)
3. ^G.L. Miessler; D.A. Tarr (2003), Inorganic Chemistry (2nd ed.), Pearson Prentice–Hall, ISBN0-13-035471-6
4. ^Lewis, G. N. (1916), 'The Atom and the Molecule', J. Am. Chem. Soc., 38 (4): 762–85, doi:10.1021/ja02261a002
5. ^Miburo, Barnabe B. (1993), 'Simplified Lewis Structure Drawing for Non-science Majors', J. Chem. Educ., 75 (3): 317, Bibcode:1998JChEd..75..317M, doi:10.1021/ed075p317
6. ^Lever, A. B. P. (1972), 'Lewis Structures and the Octet Rule', J. Chem. Educ., 49 (12): 819, Bibcode:1972JChEd..49..819L, doi:10.1021/ed049p819
7. ^Miessler, G. L. and Tarr, D. A., Inorganic Chemistry (2nd ed., Prentice Hall 1998) ISBN0-13-841891-8, pp. 49–53 – Explanation of formal charge usage.

External links[edit]

What is a Lewis Diagram?

Lewis diagrams, also called electron-dot diagrams, are used to represent paired and unpaired valence (outer shell) electrons in an atom. For example, the Lewis diagrams for hydrogen, helium, and carbon are

where the symbol represents the element (in this case, hydrogen, helium, and carbon) and the dots represent the electrons in the outer shell (in this case, one, two, and four). These diagrams are based on the electron structures learned in the Atomic Structure and Periodic Table chapters.

What is a Lewis Structure?

The Lewis structure is used to represent the covalent bonding of a molecule or ion. Covalent bonds are a type of chemical bonding formed by the sharing of electrons in the valence shells of the atoms. Covalent bonds are stronger than the electrostatic interactions of ionic bonds, but keep in mind that we are not considering ionic compounds as we go through this chapter. Most bonding is not purely covalent, but is polar covalent (unequal sharing) based on electronegativity differences.

The atoms in a Lewis structure tend to share electrons so that each atom has eight electrons (the octet rule). The octet rule states that an atom in a molecule will be stable when there are eight electrons in its outer shell (with the exception of hydrogen, in which the outer shell is satisfied with two electrons). Lewis structures display the electrons of the outer shells because these are the ones that participate in making chemical bonds.

How to Build a Lewis Structure?

For simple molecules, the most effective way to get the correct Lewis structure is to write the Lewis diagrams for all the atoms involved in the bonding and adding up the total number of valence electrons that are available for bonding. For example, oxygen has 6 electrons in the outer shell, which are the pattern of two lone pairs and two singles. If the electrons are not placed correctly, one could think that oxygen has three lone pairs (which would not leave any unshared electrons to form chemical bonds). After adding the four unshared electrons around element symbol, form electron pairs using the remaining two outer shell electrons.

Incorrect Structure

Correct Structure

are two hydrogen atoms and one oxygen atom. The Lewis structure of each of these atoms would be as follows:

One good example is the water molecule. Water has the chemical formula of H₂O, which means there

We can now see that we have eight valence electrons (six from oxygen and one from each hydrogen). With few exceptions, hydrogen atoms are always placed on the outside of the molecule, and in this case the central atom would be oxygen. Each of the two unpaired electrons of the oxygen atom will form a bond with one of the unpaired electrons of the hydrogen atoms. The bonds formed by the shared electron pairs can be represented by either two closely places dots between two element symbols or more commonly by a straight line between element symbols:

Let us try another one.

Example: Write the Lewis structure for methane (CH₄).
Answer:Hydrogen atoms are always placed on the outside of the molecule, so carbon should be the central atom.

After counting the valence electrons, we have a total of 8 [4 from carbon + 4(1 from each hydrogen] = 8.

Each hydrogen atom will be bonded to the carbon atom, using two electrons. The four bonds represent the eight valence electrons with all octets satisfied, so your structure is complete.

Lewis Dot Structure Calculator Online Tool

Example: Write the Lewis structure for carbon dioxide (CO₂).
Answer:Carbon is the lesser electronegative atom and should be the central atom.

After counting the valence electrons, we have a total of 16 [4 from carbon + 2(6 from each oxygen)] = 16.

Each oxygen atom has two unshared electrons that can be used to form a bond with two unshared electrons of the carbon atom, forming a double bond between the two atoms. The remaining eight electrons will be place on the oxygen atoms, with two lone pairs on each.

Lewis Structures of Polyatomic Ions

Building the Lewis Structure for a polyatomic ion can be done in the same way as with other simple molecules, but we have to consider that we will need to adjust the total number of electrons for the charge on the polyatomic ion. If the ion has a negative charge, the number of electrons that is equal to the charge on the ion should be added to the total number of valence electrons. If the ion has a positive charge, the number of electrons that is equal to the charge should be subtracted from the total number of valence electrons. After writing the structure, the entire structure should then be placed in brackets with the charge on the outside of the brackets at the upper right corner.

Example: Write the Lewis structure for the ammonium ion (NH₄⁺).
Answer: Hydrogen atoms are always placed on the outside of the molecule, so nitrogen should be the central atom.

After counting the valence electrons, we have a total of 9 [5 from nitrogen + 4(1 from each hydrogen)] = 9. The charge of +1 means an electron should be subtracted, bringing the total electron count to 8.

Each hydrogen atom will be bonded to the nitrogen atom, using two electrons. The four bonds represent the eight valence electrons with all octets satisfied, so your structure is complete. (Do not forget your brackets and to put your charge on the outside of the brackets)

Example: Write the Lewis structure for the hydroxide ion (OH^-).

Answer: Since there are only two atoms, we can begin with just a bond between the two atoms.

After counting the valence electrons, we have a total of 7 [6 from Oxygen + 1 from each Hydrogen)] = 7. The charge of -1 indicates an extra electron, bringing the total electron count to 8.

Oxygen will be bonded to the hydrogen, using two electrons. Place the remaining six electrons as three lone pairs on the oxygen atom. All octets are satisfied, so your structure is complete. (Do not forget your brackets and to put your charge on the outside of the brackets)

Lewis Structures for Resonance Structures

The existence of some molecules often involves two or more structures that are equivalent. Resonance can be shown using Lewis structures to represent the multiple forms that a molecule can exist. The molecule is not switching between these forms, but is rather an average of the multiple forms. This can be seen when multiple atoms of the same type surround the central atom. When all lone pairs are placed on the structure, all the atoms may still not have an octet of electrons. To deal with this problem, the atoms (primarily in a C, N, or O formula) form double or triple bonds by moving lone pairs to form a second or third bond between two atoms. The atom that originally had the lone pair does not lose its octet because it is sharing its lone pair. Double-headed arrows are placed between the multiple structures of the molecule or ion to show resonance.

Let us look at how to build a nitrate ion (NO₃^-).

Nitrogen is the least electronegative atom and should be the central atom.

After counting the valence electrons, we have a total of 23[5 from nitrogen + 3(6 from each oxygen)] = 23. The charge of -1 indicates an extra electron, bringing the total electron count to 24.

Each oxygen atom will be bonded to the nitrogen atom, using a total of six electrons. We then place the remaining 18 electrons initially as 9 lone pairs on the oxygen atoms (3 pairs around each atom).

Although all 24 electrons are represented in the structure (two electrons for each of the three bonds and 18 for each of the nine lone pairs), the octet for the nitrogen atom is not satisfied. To satisfy the octet rule for the nitrogen atom, a double bond needs to be made between the nitrogen and one of the oxygen atoms. Because of the symmetry of the molecule, it does not matter which oxygen atoms is chosen. Because there are three different oxygen atoms that could form the double bond, there will be three different resonance structures showing each oxygen atom with a double bond to the nitrogen atom. Double-headed arrows will be placed between these three structures. (Do not forget your brackets and to put your charge on the outside of the brackets)

Example: What is the Lewis structure for the nitrite ion (NO₂⁻)?

Answer: Nitrogen is the least electronegative atom and should be the central atom.

After counting the valence electrons, we have a total of 17 [5 from nitrogen + 2(6 from each oxygen)] = 17. The charge of -1 indicates an extra electron, bringing the total electron count to 18.

Lewis Dot Structure Practice Worksheet

Each oxygen will be bonded to the nitrogen, using two electrons. Place the remaining 16 electrons initially as nine lone pairs on the oxygen atoms (3 pairs around each atom) and the nitrogen (one pair).

Although all 18 electrons are represented in the structure (2 electrons for each of the two bonds and 14 for each of the seven lone pairs), the octet for the nitrogen atom is not satisfied. To satisfy the octet rule for the nitrogen atom, a double bond needs to be made between the nitrogen atom and one of the oxygen atoms. Because of the symmetry of the molecule, it does not matter which oxygen is chosen. Because there are two different oxygen atoms that could form the double bond, there will be two different resonance structures showing each oxygen atom with a double bond to the nitrogen atom. A double-headed arrow will be placed between these structures. (Do not forget your brackets and to put your charge on the outside of the brackets)

Lewis Structures for Electron-rich Compounds

Elements with atomic number greater than 13 often form compounds or polyatomic ions in which there are “extra” electrons. For these compounds we proceed as above. Once all of the octets are satisfied, the extra electrons are assigned to the central atom either as lone pairs or an increase in the number of bonds. (Never use multiple bonds with these compounds—you already have too many electrons.)

Example: Draw the Lewis structure for phosphorus pentafluoride, PF₅.

Answer:The electronegativity of fluorine is greater than that of phosphorus—so the phosphorus atom is placed in the center of the molecule.

The total number of electros is 40 [5(7 from each fluorine) + 5 from the phosphorus] = 40. Using a single bond between the phosphorus atom and each of the fluorine atoms and filling the remaining electrons to satisfy the octet rule for the fluorine atoms accounts for all 40 electrons. Note that there are five bonds around the central atom.

Lewis Structures for Electron-poor Compounds

There is another type of molecule or polyatomic ion in which there is an electron deficiency of one or more electrons needed to satisfy the octets of all the atoms. In these cases, the more electronegative atoms are assigned as many electrons to complete those octets first and then the deficiency is assigned to the central atom.

Example: Draw the Lewis structure for boron trifluoride, BF₃.

Answer:The electronegativity of fluorine is greater than that of boron—so the boron atom is placed in the center of the molecule.

The total number of electron is 24 [3(7 from each fluorine) + 3 from boron] = 24. Using a single bond between the boron and each of the fluorine atoms and filling the remaining electron as lone pairs around the fluorine atoms to satisfy the octets accounts for all 24 electrons.

Lewis Dot Structure Calculator Online Math

The boron atom is two electrons shy of its octet. You may ask about the formation of a double bond (and even resonance). But, fluorine and boron are not in the list that can form double bonds (C, N, O, P, S) and so the compound is electron poor.

Try It Out!

Draw the Lewis structure for the following:

1. Hydronium ion (H₃O⁺)
2. Hypochlorite ion (ClO^-)
3. Carbonate ion (CO₃^-2)
4. Ammonia (NH₃)
5. Hydrogen fluoride (HF)
6. Ozone (O₃)
7. Xenon difluoride (XeF₂)