What are the reagents in an iodoform reaction

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SUMMARY

The iodoform reaction involves the conversion of 2-butanone using sodium hydroxide and iodine in water, resulting in the formation of iodoform and sodium propanoate. Reagents P and Q are sodium hydroxide and iodine, while reagent R is a strong acid, such as HCl or H2SO4, necessary for converting sodium propanoate to propanoic acid. This reaction exemplifies the haloform reaction mechanism, which is crucial for organic synthesis involving methyl ketones.

PREREQUISITES
  • Understanding of organic chemistry reactions, specifically haloform reactions.
  • Familiarity with the properties and reactions of 2-butanone.
  • Knowledge of sodium hydroxide and iodine as reagents in organic synthesis.
  • Basic principles of acid-base reactions in organic chemistry.
NEXT STEPS
  • Research the mechanism of the haloform reaction in detail.
  • Study the role of strong acids in organic reactions, focusing on HCl and H2SO4.
  • Explore the synthesis of carboxylic acids from ketones and their derivatives.
  • Investigate the applications of iodoform in organic chemistry and its significance in synthesis.
USEFUL FOR

Organic chemistry students, chemistry educators, and researchers involved in synthetic organic chemistry will benefit from this discussion, particularly those focusing on reaction mechanisms and organic synthesis techniques.

lioric
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Homework Statement


this question is about the organic reactions shown in the diagram. ( diagram shows that butan2one is reaction with a reagent P and Q and then reagent R and forms propanoic acid and iodoform)

a)name the reagents P and Q used in reaction 1.
b) identify the reagent R used in reaction 1 and explain why it is needed

Homework Equations


I do know that for iodoform reaction you need sodium hydroxide in iodine solution
But I'm wondering what the Reagent R is

The Attempt at a Solution

 
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lioric said:
I do know that for iodoform reaction you need sodium hydroxide in iodine solution
What are the products you get if you just put in sodium hydroxide and iodine in water?
Edit: and of course 2-butanone.
 
Last edited:
TeethWhitener said:
What are the products you get if you just put in sodium hydroxide and iodine in water?
Edit: and of course 2-butanone.

NaI and NaOI and water
 
lioric said:
NaI and NaOI and water
What are the organic products?
Edit: maybe my edit in post 2 wasn’t clear. When you combine 2-butanone, sodium hydroxide, and iodine in water, what are the organic products?
 
TeethWhitener said:
What are the organic products?
Edit: maybe my edit in post 2 wasn’t clear. When you combine 2-butanone, sodium hydroxide, and iodine in water, what are the organic products?

Iodoform and sodium propanoate
 
lioric said:
Iodoform and sodium propanoate
So if you want to end up with propanoic acid, what do you have to do?
 
TeethWhitener said:
So if you want to end up with propanoic acid, what do you have to do?

I have seen two versions of this

1) In a haloform reaction with iodine, bromine, or chlorine, methyl ketones are converted into the corresponding carboxylic acid and haloform. (from site chemgapedia
http://www.chemgapedia.de/vsengine/...ik/c_acid/synthese_von_carbonsaeuren.vlu.html

2) the other from McMurry organic chemistry textbook saying that in if we use excess halogen and base than it will form the carboxilic acid
And this link shows it too
https://goo.gl/images/miAQfp
 
Last edited:
You’re overthinking things. If you have sodium propanoate and you want propanoic acid, what do you need to do?
 
TeethWhitener said:
You’re overthinking things. If you have sodium propanoate and you want propanoic acid, what do you need to do?

Add a strong acid like HCl or H2SO4

Salt + acid makes a weaker acid and another salt
 
  • #10
lioric said:
Add a strong acid like HCl or H2SO4

Salt + acid makes a weaker acid and another salt
Right. So now just put it all together.
 

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