Maximum Covalent Bonds Formed by Carbon with Nitrogen?

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Discussion Overview

The discussion revolves around the maximum number of covalent bonds that carbon can form with nitrogen, exploring theoretical and practical aspects of bonding in chemistry. It includes considerations of valency, specific compounds, and historical context.

Discussion Character

  • Homework-related
  • Debate/contested
  • Exploratory

Main Points Raised

  • One participant notes that they have not encountered a compound with more than 3 C-N bonds, questioning the validity of a source that states the maximum is 4.
  • Another participant asks about the maximum number of bonds carbon can form with any element, indicating a broader inquiry into carbon's bonding capabilities.
  • A participant highlights the ambiguity in the question regarding whether it refers to bonding with the same nitrogen atom.
  • One participant suggests that if only one nitrogen atom is considered, the maximum would be 3, while also questioning the scenario if hydrogen were involved instead.
  • Another participant confirms that carbon has a valency of 4 but expresses skepticism about carbon forming 4 bonds with a single atom, leaning towards 3 as a more realistic maximum.
  • A claim is made that the bond order in C2 is 4, introducing a theoretical perspective on carbon bonding.
  • A historical reference is made to tetranitromethane, noting its existence and sensitivity, while also mentioning past industrial attempts to produce it that ended in disaster.

Areas of Agreement / Disagreement

Participants express differing views on the maximum number of covalent bonds carbon can form with nitrogen, with no consensus reached on whether it is 3 or 4. The discussion remains unresolved regarding the specifics of bonding scenarios.

Contextual Notes

There are limitations in the assumptions made about bonding scenarios, particularly regarding the interpretation of the question and the specific conditions under which carbon-nitrogen bonding is being evaluated.

subhradeep mahata
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Homework Statement


What is the maximum number of covalent bonds formed by carbon with nitrogen?
A)2 B)3 C)4 D)1

Homework Equations

The Attempt at a Solution


I have not come across a single compound which has more than 3 C-N bonds. But my book is giving the answer as 4. Now, I am not sure whether this has to do with the extra lone pair of electrons on nitrogen atom or not, but i will be grateful to you if you could just help me out. Thanks.
 
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What is the maximum number of bonds carbon can form with any element?
 
It does not say with the same nitrogen atom, does it?
 
@DrDu No it does not say,but it would have been a really stupid question then. Suppose there had been hydrogen in place of nitrogen, would the answer would have been 4 then?
Let's say there is only one nitrogen atom, then would it be 3?
 
@Borek Carbon has a valency 4, so at most it can form 4 covalent bonds, but i have not seen carbon forming those 4 bonds with only one other atom. So, i guess it is 3.
 
It has been argued that the bond order in C2 is 4.
 
Well looking up Wikipedia it appears that tetranitromethane has been known since the 1860s. So for theory you see no reason why it shouldn't exist and it does exist. In practice you are unlikely to meet it. Trouble is it is more sensitive to percussion than TNT! And As far as I can make out there are some small applications, but big ones tend to meet this kind of end:

"This method was attempted on an industrial scale in the 1950s by Nitroform Products Company in Newark, USA, but the entire plant was destroyed by an explosion in 1953.[8]"
 

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