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For the two resonance structures of formamide in Problem 2, explain why each of

ID: 1062246 • Letter: F

Question

For the two resonance structures of formamide in Problem 2, explain why each of the following statements is either correct or incorrect. The molecule is not oscillating back-and-forth between the two structures; the molecule is. instead, an average or superposition of the two structures. The expected CO bond length is between that for a normal CO double bond and that for a normal CO single bond. The nitrogen in the molecule has a lower electron density associated with it than is found for the free nitrogen atom. Both resonance structures have the same energy

Explanation / Answer

3. Resonace structures for formamide.

a) The molecule does not oscillate back-and-forth between the teo structures, instead the structure of formamide is an average of two strutures : true

A neutral structure arising by the average of the two structures is lowest ebergy and thus most stable.

b) The expected CO bond length is between normal CO double bond and that for a single bond : True.

The lone pair migration towards N-C leads to a lesser double bond character for CO bond.

c) The nitrogen in the molecule has lower electron density than found for free nitrogen : True

The nitrogen in resonance has lower electron density.

d) Both resonance structures are of same energy : False

the one with postive charge on carbon is of lower energy than the one with nitrogen having +ve charge.

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