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Date: 11-10-2019
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Date: 27-8-2019
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Date: 23-10-2019
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Methyl ketones typically undergo halogenation three times to give a trihalo ketone due to the increased reactivity of the halogenated product as discussed above. This trihalomethyl group is an effective leaving group due to the three electron withdrawing halogens and can be cleaved by a hydroxide anion to effect the haloform reaction. The product of this reaction is a carboxylate and a haloform molecule (CHCl3, CHBr3, CHI3). Overall the haloform reaction represents an effective method for the conversion of methyl ketones to carboxylic acids. Typically, this reaction is performed using iodine because the subsequent iodoform (CHI3) is a bright yellow precipitate which is easily filtered off.
General reaction
Example: The Haloform Reaction
1) Formation of the trihalo species
2) Nulceophilic attack on the carbonyl carbon
3) Removal of the leaving group
4) Deprotonation
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