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8.5 Haloform Reaction
When each of the compounds is treated with hydroxide, draw the enolate that would be generated.
Make sure you draw all resonance structures.
We learned how to make enolates in the previous section.
We will see what an enolate can do.
The reaction between an enolate and a halogen will be explored in this section.
The reactions between an enolate and other electrophiles will be explored in the following sections.
This enolate can be formed in the presence of br.
The enolate expels Br as a leaving group.
The reaction goes on.
The base is still present in the solution.
Another alpha proton can be removed with hydroxide.
The CH group has been converted into a CBr group.
You should be uncomfortable at this point.
This is a rare exception to the golden rule.
This is one of the rare cases where a C- can be stable enough for it to serve as a leaving group.
The loss of this leaving group is caused by the formation of the stable carbonyl group.
Even though it can leave, it is not the most stable anion on the planet.
It is not as stable as a carboxylate ion.
This forms a carboxylate anion.
This is the end of our mechanism.
Iodoform is a yellow solid.
This reaction can be used to investigate the identity of a compound.
If the compound is a methyl ketone, it will produce iodoform under these conditions.
The chemical test is a relic of the past.
It is still used in textbook problems.
An unknown compound tests positive for iodoform.
The problem begins when you are told that you have a drug.
You should know what this means if you see it in your textbook.
There is more use for this reaction.
It can be used to solve synthesis problems.
The haloform reaction is most efficient when the other side of the ketone has no protons.
This is a new example of a "cross-over" reaction.
In the previous chapter, we talked about how to convert ketones into carboxylic acid derivatives.
The process that we explored in this section can be used to make a carboxylic acid.
You should add this to your collection.
Draw a mechanism for the transformation in the previous Problem on a separate piece of paper.
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