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Chapter 9: Problem 106

Write three resonance structures for the isocyanate ion (CNO \(^{-}\) ). Rank them in importance.

Short Answer

Expert verified
The three resonance structures of the isocyanate ion (CNO \(^{-}\)) could be drawn as one with a C≡N and a C=O, another with a C=N and a C≡O, and a third with a C≡N and a C-O. The second and third structures are more important as they are more stable having less charge separation.

Step by step solution

01

Basic Lewis Structure

Start by figuring out the basic Lewis structure. Carbon (C) has 4 valence electrons, Nitrogen (N) has 5 valence electrons, and Oxygen (O) has 6 valence electrons. Also, there is an extra electron for the negative charge of the ion. Therefore, total available valence electrons are 4+5+6+1=16 electrons. The least electronegative atom Carbon is placed in the centre, with Nitrogen and Oxygen at the sides. Arrange the electrons to fill the outer (valence) energy levels of each atom. Remember that each line (bond) represents a pair of electrons.
02

Drawing Resonance Structures

Resonance structures differ only in the placement of their electrons. In the first structure, draw a single bond between Carbon and Nitrogen and a triple bond between Carbon and Oxygen giving everything a full octet. In the second structure, shift the π (pi) bond between C and O to give O an extra lone pair and move the N-C π bond electrons to fill in the spot, creating a C=O double bond and N≡C triple bond. For the third structure, shift the N-C π bond electrons again (as in step two) to create the N≡C triple bond and a C-O single bond.
03

Ranking the Structures

Rank the structures based on stability. The structures with least charge separation are more favorable. In the first structure, there are formal charges on N (negative) and O (positive), so this is less favorable. The second and third structures are equivalent and more favorable with only one formal charge (negative) on O or N.

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Most popular questions from this chapter

Write the Lewis dot symbols of the reactants and products in the following reactions. (First balance the equations.) (a) \(\mathrm{Sr}+\mathrm{Se} \longrightarrow \mathrm{SrSe}\) (b) \(\mathrm{Ca}+\mathrm{H}_{2} \longrightarrow \mathrm{CaH}_{2}\) (c) \(\mathrm{Li}+\mathrm{N}_{2} \longrightarrow \mathrm{Li}_{3} \mathrm{~N}\) (d) \(\mathrm{Al}+\mathrm{S} \longrightarrow \mathrm{Al}_{2} \mathrm{~S}_{3}\)

For each of the following pairs of elements, state whether the binary compound they form is likely to be ionic or covalent. Write the empirical formula and name of the compound: (a) I and \(\mathrm{Cl}\), (b) \(\mathrm{Mg}\) and \(\mathrm{F}\).

What is the difference between a Lewis dot symbol and a Lewis structure?

List these bonds in order of increasing ionic character: the lithium-to- fluorine bond in \(\mathrm{LiF},\) the potassium-to-oxygen bond in \(\mathrm{K}_{2} \mathrm{O},\) the nitrogen-tonitrogen bond in \(\mathrm{N}_{2}\), the sulfur-to-oxygen bond in \(\mathrm{SO}_{2}\), the chlorine-to-fluorine bond in \(\mathrm{ClF}_{3}\).

Draw a Lewis structure for each of these organic molecules in which the carbon atoms are bonded to each other by single bonds: \(\mathrm{C}_{2} \mathrm{H}_{6}, \mathrm{C}_{4} \mathrm{H}_{10}, \mathrm{C}_{5} \mathrm{H}_{12}\).
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