MediumChemistryHigh School (11–12)Organic Chemistry: Some Basic Principles and Techniques › Electronic Effects and Reaction IntermediatesNumerical
In the nitrate ion, NO₃⁻, the nitrogen atom is joined to three oxygen atoms…
Contributed by StemPy LabTry it on paper first. A hint, the key idea and the worked solution are here when you need them.
In the nitrate ion, , the nitrogen atom is joined to three oxygen atoms. Each resonance structure has one bond and two bonds, and the nitrogen carries a charge of .
Find the number of resonance structures, the bond order of each N-O bond in the hybrid, and the average charge on each oxygen atom, in units of . Give the charge without its sign.
Need a reminder? The key ideaShow
The inductive effect is a permanent pull () or push () of electrons along sigma bonds. It fades with distance. Resonance spreads pi electrons and lone pairs over several atoms. The hybrid is more stable than any one structure, and its equal bonds share the bond order. The electromeric effect is a temporary shift of a pi pair under attack. Hyperconjugation spreads the sigma electrons of an alpha C-H bond, so more alpha hydrogens mean more stability.
The worked solution
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Work it out on paper first. It is fine to get stuck or make a mistake: that is how we learn. When you are ready, go through the solution one step at a time, and check each step against your own.
Step 1. Structures. The double bond can be on any one of three oxygen atoms. That makes structures.
Step 2. Bond order. Each structure has a total bond order of over three bonds. The hybrid shares it equally: .
Step 3. Charge. The oxygen charges in one structure are , and . The average is , so each oxygen carries .
Answer: structures; bond order ; charge on each oxygen.
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