Alcoholic Ammonia vs Aqueous for Treating Haloalkanes

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Discussion Overview

The discussion centers on the use of alcoholic ammonia versus aqueous ammonia in the treatment of haloalkanes to form amines, as well as the use of alcoholic silver cyanide compared to aqueous silver cyanide for producing alkyl isocyanides. The scope includes theoretical and conceptual aspects of nucleophilicity and solvent effects in organic reactions.

Discussion Character

  • Conceptual clarification
  • Debate/contested

Main Points Raised

  • One participant questions why alcoholic ammonia is preferred over aqueous ammonia for treating haloalkanes to form amines.
  • Another participant suggests that water is a good nucleophile, and using alcohol solvents reduces undesired alcohol formation.
  • A different participant agrees with the previous point and adds that haloalkanes do not dissolve well in water, making alcohol a better solvent for facilitating reactions.
  • Another comment references the importance of protic polar solvents and suggests looking into the SN2 and elimination reaction concepts for further understanding.

Areas of Agreement / Disagreement

Participants express varying viewpoints on the role of solvents in these reactions, with some agreeing on the limitations of water as a solvent for haloalkanes, while others provide additional context without reaching a consensus on all points.

Contextual Notes

There are references to specific solvent properties and their effects on reaction mechanisms, but the discussion does not resolve the complexities of these interactions or the implications for reaction outcomes.

ambuj123
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Why do we use alcoholic Ammonia not Ammonia only or aqueous ammonia while using it to treat haloalkanes to form primary,secondary or tertiary amines.
same for treatment of haloalkanes with alcoholic silver cyanide to form alkyl iso cyanide.why don't we use aqueos AgCN
Thanx
 
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Probably because water is a pretty good nucleophile in its own right. Using alcohol solvents limits the amount of undesired alcohol formation.
 
I agree with Movies, and want to add something more; haloalkanes don't like water at all, it cannot be dissolved in it. Alcohol is a good solvent to solvatize haloalkanes, providing enough particles to react with each other.

Ammonia is a base, and if you trap it in a solvent, it can "live" for a prolonged period, sometimes enough to cause something in the solution.
 
chem tr seems to have the main point, read up on protic polar solvents, this subject is probably under the SN2, elimination reaction introduction chapter.
 
THanx

Thank you for the help
 

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