Single Choice

The correct stability order of the following resonating structures is: (I) $$H_2C = \overset{+}{N} = \overset{-}{N}$$ (II) $$H_2\overset{+}{C}-N=\overset{-}{N}$$ (III) $$H_2\overset{-}{C} - \overset{+}{N} \equiv N$$ (IV) $$H_2\overset{-}{C} - N = \overset{+}{N}$$

A(I) > (II) > (IV) > (III)
B(I) > (III) > (II) > (IV)
C(II) > (I) > (III) > (IV)
D(III) > (I) > (IV) > (II)
Correct Answer

Solution

D. III>I>IV>II
Lewis structure and the octet rule is followed for diazomethane. In st. III the negative charge is on C atom which is more electronegative than N so it is more stable and central atom N is sp hybridized. The terminal nitrogen atom is expected to be $$sp^2$$ hybridized so the stability is for st.I as both N are doubly bonded. In structure IV C atom is carrying a negative charge and terminal N is $$sp^2$$ hybridized. In st.II carbon does not follow octet rule so it is least stable.

SIMILAR QUESTIONS

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Draw the resonance structures for $$CH_3CH = CH\overset{+}CH_2$$. Show the electron shift using curved-arrow notation.

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