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3.45

Posted: Fri May 18, 2018 3:28 pm
by Fiona Grant 1I
Draw the Lewis structures that contribute to the resonance hybrid of nitryl chloride, ClNO2 (N is the central atom).

I know that for the Lewis structure, there are two single bonds and one double bond. The answer key shows that the 2 possible resonance structures have the double bond between N and either O atom. I was wondering why there can't be a third resonance structure with the double bond between N and Cl?

Re: 3.45

Posted: Fri May 18, 2018 3:29 pm
by Natalie Noble 1G
When you do the resonant structures look at the formal charge.

When the oxygen is double bonded that oxygens charge is 0
The other oxygen charge is -1
The nitrogen charge is +1
The chloride charge is 0

So the charges are all minimized. And the bonds for the oxygens are hybrid.

If you put the double bond on the Cl
The oxygen charge is -1 (2 of them)
The nitrogen charge is +1
The chloride charge is +1

This does not has the formal charges minimized, so it is not the best structure

You wanna keep the formal charges as close to zero as you can and putting the double bond of Cl gets you further from that goal.

It isn’t resonance when you double bond the Cl because you changed the molecule too much, it wouldn’t be able to blend(flip back and forth)