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Question: The correct order of stabilities of the following resonance structures is: (I) $H_2C-\overset{\omin...

The correct order of stabilities of the following resonance structures is:

(I) H2CNNH_2C-\overset{\ominus}{N}\equiv \overset{\oplus}{N} (II) H2C=NNH_2\overset{\oplus}{C}=N-\overset{\ominus}{N}

(III) H2CN=NH_2\overset{\ominus}{C}-N= \overset{\oplus}{N} (IV) H2CN=NH_2\overset{\oplus}{C}-N= \overset{\ominus}{N}

A

I > II > IV > III

B

I > III > II > IV

C

II > I > III > IV

D

III > I > IV > II

Answer

I > II > IV > III

Explanation

Solution

To determine the stability of resonance structures, we follow a set of rules in decreasing order of importance:

  1. Octet Rule: Structures where all atoms (especially C, N, O) have complete octets are generally the most stable.
  2. Number of Covalent Bonds: Structures with a greater number of covalent bonds are more stable.
  3. Charge Separation: Structures with less charge separation are more stable. If charges are present, structures with minimal charge separation are preferred.
  4. Electronegativity: Negative charge on a more electronegative atom and positive charge on a less electronegative atom is more favorable.
  5. Adjacent Charges: Structures with like charges on adjacent atoms are highly unstable.

Applying these rules, the stability order is I > II > IV > III.