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Chapter 11: Problem 44

In which of the following ions would you expect to find delocalized molecular orbitals: (a) \(\mathrm{HCO}_{2}^{-} ;\) (b) \(\mathrm{CO}_{3}^{2-}\) (c) \(\mathrm{CH}_{3}^{+} ?\) Explain.

Short Answer

Expert verified
The ions \( \mathrm{HCO}_{2}^{-} \) and \( \mathrm{CO}_{3}^{2-} \) have delocalized molecular orbitals while the ion \( \mathrm{CH}_{3}^{+} \) does not.

Step by step solution

01

Understanding Delocalized Molecular Orbitals

Delocalization is the extension of a pi electron cloud over more than two atoms. It is a characteristic feature of aromatic compounds and compounds with resonance. The delocalization lowers the potential energy of the system and increases stability.
02

Analyze Structure of \( \mathrm{HCO}_{2}^{-} \) Ion

In \( \mathrm{HCO}_{2}^{-} \) (Formate ion), the negative charge is shared between two oxygen atoms. This system exhibits resonance, and therefore the electrons forming the bond between carbon and oxygen are delocalized. Hence, there are delocalized molecular orbitals.
03

Analyze Structure of \( \mathrm{CO}_{3}^{2-} \) Ion

The ion \( \mathrm{CO}_{3}^{2-} \) (Carbonate ion) exhibits resonance. The negative charge is shared by three oxygen atoms and the electrons forming the bonds are delocalized. So, there are delocalized molecular orbitals.
04

Analyze Structure of \( \mathrm{CH}_{3}^{+} \) Ion

The ion \( \mathrm{CH}_{3}^{+} \) (Methyl cation) doesn't have a resonance, and therefore, the electrons forming the bond aren't delocalized. Consequently, this ion doesn't have delocalized molecular orbitals.

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Most popular questions from this chapter

Propose a hybridization scheme to account for bonds formed by the central carbon atom in each of the following molecules: (a) hydrogen cyanide, HCN; (b) methyl alcohol, \(\mathrm{CH}_{3} \mathrm{OH} ;\) (c) acetone, \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CO}\) (d) carbamic acid,

Briefly describe each of the following ideas: (a) hybridization of atomic orbitals; (b) \(\sigma\) -bond framework; (c) Kekulé structures of benzene, \(\mathrm{C}_{6} \mathrm{H}_{6}\) (d) band theory of metallic bonding.

Which of the following substances, when added in trace amounts to germanium, would produce an n-type semiconductor: (a) sulfur, (b) aluminum, (c) tin, (d) cadmium sulfide, (e) arsenic, (f) gallium arsenide? Explain.

Indicate which of the following molecules and ions are linear, which are planar, and which are neither. Then propose hybridization schemes for the central atoms. (a) \(\mathrm{Cl}_{2} \mathrm{C}=\mathrm{CCl}_{2} ;(\mathrm{b}) \mathrm{N} \equiv \mathrm{C}-\mathrm{C} \equiv \mathrm{N} ;(\mathrm{c}) \mathrm{F}_{3} \mathrm{C}-\mathrm{C} \equiv \mathrm{N}\) (d) \([\mathrm{S}-\mathrm{C} \equiv \mathrm{N}]^{-}\)

Explain why the concept of delocalized molecular orbitals is essential to an understanding of bonding in the benzene molecule, $\mathrm{C}_{6} \mathrm{H}_{6}$
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