What causes the release of ammonia in organic compounds?

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Discussion Overview

The discussion revolves around the conditions and reactions that lead to the release of ammonia from organic compounds, particularly focusing on the role of bases in this process. Participants explore various chemical reactions and the strength of different bases in relation to ammonium ions.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested
  • Mathematical reasoning

Main Points Raised

  • Some participants propose that compounds more basic than ammonia can liberate it, but the specifics of these reactions need to be clarified.
  • One participant emphasizes the importance of reaction equations, specifically mentioning the reaction of NH4Cl with NaOH as illustrative.
  • Another participant questions the relevance of NaOH in the context of the discussion, seeking to understand its role in the reaction.
  • There is a suggestion that NaNH2 might also react with NH4Cl due to its strong basicity, although uncertainty remains about the general concept.
  • Participants discuss the strength of bases required to abstract a proton from NH4+, with some expressing confusion about determining which bases are sufficiently strong.
  • One participant notes that while urea is not a base, other listed substances are, with varying strengths, but lacks clarity on how strong a base needs to be for the reaction.
  • Another participant suggests that when two bases compete for a proton, the stronger base will prevail, prompting questions about how to identify strong bases.
  • It is mentioned that consulting tables of acid dissociation constants (Ka) might provide insights into the reactivity of different nitrogen-containing compounds.

Areas of Agreement / Disagreement

Participants express uncertainty about the specific bases that can liberate ammonia and the criteria for their strength. There is no consensus on the exact conditions or reactions involved, and multiple viewpoints on the role of different bases remain present.

Contextual Notes

Limitations include a lack of clarity on the strength of various bases and their ability to abstract protons from NH4+. The discussion also depends on the definitions of basicity and the specific reactions being considered.

Gourab_chill
Messages
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Homework Statement
I have given a number of compounds and asked which of them liberate ammonia when rected with NH4Cl( see the attachment for the complete question)
Relevant Equations
no equations probably
I don't really have any idea how to approach this, but the answer says that it is the compounds which are more basic than ammonia liberate it.
 

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I am afraid It is all in the reaction equations.

First things first: can you write reaction equation for NH4Cl with NaOH? While NaOH is not present on the list, it is exactly type of the reaction that is important here.
 
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Borek said:
I am afraid It is all in the reaction equations.

First things first: can you write reaction equation for NH4Cl with NaOH? While NaOH is not present on the list, it is exactly type of the reaction that is important here.

Well the reaction is NH4Cl + NaOH --> NaCl + H2O + NH3

But what has NaOH to do with it?
 
Gourab_chill said:
Well the reaction is NH4Cl + NaOH --> NaCl + H2O + NH3

But what has NaOH to do with it?
It's for illustrational purposes, and you seem to me to have grasped the concept, without realizing that @Borek's point was for you to grasp the concept.
 
Now that you know what is the idea behind, can you think which of the substances listed will react with the NH4Cl to produce ammonia?
 
Borek said:
Now that you know what is the idea behind, can you think which of the substances listed will react with the NH4Cl to produce ammonia?

I would guess NaNH2 as Nh2- is a stong base like NaOH?
I'm not quite sure - i cannot understand the basic idea behind this question.
 
Is the NaNH2 the only base between the substances given?

How strong has the base be to steal H+ from NH4+?
 
No except urea all the other are bases, some strong and some weak.
Well I don't have much of a idea on how much strong the base has to be in order to abstract a proton from NH4+
 
Think this way: when two bases compete for a proton, which one will win - the stronger one, or the weaker one?
 
  • #10
the stronger one but how should I know which one is strong enough to react?
 
  • #11
That's what the question is about - and the only sure way to check is to look in the tables. There are some general rules though saying what to expect from different nitrogen atoms in different functional groups. My bet is that your textbook should contain them, if not, try to google for Ka tables of organic compounds (sorry, can't be more specific at the moment).
 

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