Preparing Alkyl Halides from Alcohols : Replacing -OH by iodine
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26-7-2019
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Replacing -OH by iodine
In this case, the alcohol is reacted with a mixture of sodium or potassium iodide and concentrated phosphoric(V) acid, H3PO4, and the iodoalkane is distilled off. The mixture of the iodide and phosphoric(V) acid produces hydrogen iodide, which reacts with the alcohol.
CH3CH2OH+HI→CH3CH2I+H2O
Phosphoric(V) acid is used instead of concentrated sulfuric acid because sulfuric acid oxidizes iodide ions to iodine and produces hardly any hydrogen iodide. A similar phenomenon occurs to some extent with bromide ions in the preparation of bromoalkanes but not enough to interfere with the main reaction. There is no reason why you could not use phosphoric(V) acid in the bromide case instead of sulfuric acid if desired.
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