Which of the following species exhibits resonance stabilization?
A
(methane)
B
(carbonate ion)
C
(ammonium ion)
D
(nitrite ion)
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1
Identify the concept of resonance stabilization: Resonance occurs when a molecule or ion can be represented by two or more valid Lewis structures (resonance forms) that differ only in the placement of electrons, not atoms. This delocalization of electrons leads to increased stability.
Examine each species to determine if resonance is possible by looking for multiple Lewis structures with different electron arrangements:
For methane (CH\_4), all bonds are single C-H bonds with no possibility of electron delocalization or resonance structures.
For the carbonate ion (CO\_3\^{2-}), draw the Lewis structures showing the double bond between carbon and one oxygen, and single bonds with the other oxygens carrying negative charges. These structures can be interconverted by moving the double bond among the oxygens, indicating resonance.
For ammonium ion (NH\_4\^{+}), all N-H bonds are single and there are no lone pairs or multiple bonding possibilities, so no resonance structures exist. For nitrite ion (NO\_2\^{-}), draw Lewis structures showing the double bond between nitrogen and one oxygen and a single bond with the other oxygen carrying a negative charge. These can be interconverted by shifting the double bond, indicating resonance stabilization.