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Chapter 5: Problem 158

Which one of the following is expected to have resonance forms? Explain your choice. (a) \(\mathrm{NH}_{4}^{+}\) (b) HCN (c) \(\mathrm{CO}\) (d) \(\mathrm{NO}_{2}^{-}\)

Short Answer

Expert verified
The \(\mathrm{NO}_{2}^{-}\) ion (option D) is expected to have resonance structures. This is due to its capability of redistributing its electrons in different configurations with similar energies, which is not observed in the other given molecules.

Step by step solution

01

(a) \(\mathrm{NH}_{4}^{+}\) Analysis

The \(\mathrm{NH}_{4}^{+}\) ion has a positive charge distributed among its N-H bonds and a central nitrogen atom bonded to four hydrogen atoms. All the N-H bonds are single bonds, and Nitrogen does not have any lone pairs in this structure. Therefore, there are no other possible configurations with similar energies, and the \(\mathrm{NH}_{4}^{+}\) ion doesn't have any resonance structures.
02

(b) HCN Analysis

The HCN molecule has a linear structure with single bonds between hydrogen and carbon, and a triple bond between carbon and nitrogen. Both carbon and hydrogen do not have lone pairs, so redistributing π electrons is not possible in this molecule. Therefore, HCN does not have any resonance structures.
03

(c) \(\mathrm{CO}\) Analysis

The \(\mathrm{CO}\) molecule consists of a carbon atom triple bonded to an oxygen atom. The carbon atom does not have any lone pairs, but oxygen has two lone pairs. Since there isn't another atom with the capability of redistributing electrons with similar energies, the \(\mathrm{CO}\) molecule does not have any resonance structures.
04

(d) \(\mathrm{NO}_{2}^{-}\) Analysis

The \(\mathrm{NO}_{2}^{-}\) ion has a central nitrogen atom bonded to two oxygen atoms and a negative charge distributed across the molecule. The nitrogen atom is single bonded to one oxygen atom and double-bonded to another oxygen atom. There are unpaired electrons on nitrogen and an unshared electron pair on the oxygen with the single bond. This structure allows the redistribution of electrons with similar energies.
05

Conclusion

Among the options given, the \(\mathrm{NO}_{2}^{-}\) ion (option D) is expected to have resonance structures as it is capable of redistributing its electrons in different configurations with similar energies, unlike the other molecules presented.

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Most popular questions from this chapter

Give the proper name for the following compounds: (a) \(\mathrm{Na}_{2} \mathrm{SO}_{4}\) (b) \(\left(\mathrm{NH}_{4}\right)_{3} \mathrm{PO}_{4}\) (c) \(\mathrm{KClO}\) (d) \(\mathrm{CaCO}_{3}\) (e) \(\mathrm{Al}\left(\mathrm{NO}_{3}\right)_{3}\)

Draw a dot diagram for the molecule \(\mathrm{O}_{3}\), ozone, the molecule in our upper atmosphere that protects us from the Sun's harmful ultraviolet electromagnetic radiation. (Hint: Only the middle oxygen atom forms bonds with the two other oxygen atoms.)

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