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Chapter 9: Problem 60

Draw three reasonable resonance structures for the \(\mathrm{OCN}^{-}\) ion. Show formal charges.

Short Answer

Expert verified
The three resonance structures for the OCN- ion will be: 1) Double bond between O and C, single bond between C and N, formal charge on O. 2) Single bond between O and C, double bond between C and N, formal charge on N. 3) No bond between O and C, triple bond between C and N, formal charge on O.

Step by step solution

01

Understand Resonance Structures

Resonance structures are a set of two or more Lewis Structures where the chemical connectivity is the same but the electrons are distributed differently among them. The true structure is an average of the resonance forms. In this case, the atom sequence in OCN- ion is O-C-N.
02

Draw the First Resonance Structure

For the first structure, draw a double bond between the Oxygen (O) and Carbon (C), and single bond between Carbon (C) and Nitrogen (N). Assign the negative charge to the Oxygen atom (O) since it is more electronegative. This makes it the formal charge.
03

Draw the Second Resonance Structure

In the second resonance structure, consider a double bond between Carbon (C) and Nitrogen (N), with a single bond between Oxygen (O) and Carbon (C). Also, assign the negative formal charge to the Nitrogen atom in this case.
04

Draw the Third Resonance Structure

In the third resonance structure, form triple bonds between Carbon (C) and Nitrogen (N), with no bonds between Oxygen (O) and Carbon (C). The negative formal charge will now be assigned to the Oxygen atom.

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Most popular questions from this chapter

The following species have been detected in interstellar space: (a) \(\mathrm{CH},(\mathrm{b}) \mathrm{OH},(\mathrm{c}) \mathrm{C}_{2},(\mathrm{~d}) \mathrm{HNC},(\mathrm{e}) \mathrm{HCO} .\) Draw Lewis structures for these species and indicate whether they are diamagnetic or paramagnetic.

Draw Lewis structures for the following organic molecules: (a) methanol \(\left(\mathrm{CH}_{3} \mathrm{OH}\right) ;\) (b) ethanol \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\right) ;\) (c) tetraethyllead \(\left[\mathrm{Pb}\left(\mathrm{CH}_{2} \mathrm{CH}_{3}\right)_{4}\right]\) which was used in "leaded gasoline"; (d) methylamine \(\left(\mathrm{CH}_{3} \mathrm{NH}_{2}\right),\) which is used in tanning; (e) mustard gas \(\left(\mathrm{ClCH}_{2} \mathrm{CH}_{2} \mathrm{SCH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\right),\) a poisonous gas used in World War I; (f) urea [(NH \(_{2}\) ) \(_{2}\) CO], a fertilizer; and (g) glycine \(\left(\mathrm{NH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\right)\), an amino acid.

In 1998 scientists using a special type of electron microscope were able to measure the force needed to break a single chemical bond. If \(2.0 \times 10^{29} \mathrm{~N}\) was needed to break a \(\mathrm{C}-\mathrm{Si}\) bond, estimate the bond enthalpy in \(\mathrm{kJ} / \mathrm{mol} .\) Assume that the bond had to be stretched by a distance of 2 A \(\left(2 \times 10^{-10} \mathrm{~m}\right)\) before it is broken.

Explain why the bond enthalpy of a molecule is usually defined in terms of a gas-phase reaction. Why are bond-breaking processes always endothermic and bond-forming processes always exothermic?

Write Lewis structures for the following molecules and ions: (a) \(\mathrm{OF}_{2},\) (b) \(\mathrm{N}_{2} \mathrm{~F}_{2},\) (c) \(\mathrm{Si}_{2} \mathrm{H}_{6},\) (d) \(\mathrm{OH}^{-}\), (e) \(\mathrm{CH}_{2} \mathrm{ClCOO}^{-},\) (f) \(\mathrm{CH}_{3} \mathrm{NH}_{3}^{+}\)
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