Can an tertiary haloalkane undergo nucelophilic substitution with Iodine?
Answer:
Tertiary substrates usually follow the SN1 mechanism. This follows the carbocation mechanism. SN1 is usaully carried out in a polar solvent, which aids the formation of nucleophiles.
Any compound of iodine will have a lattice energy lesser than its corresponding bromide and chloride. So, we can compensate the energy loss in bond breaking form the making up of the crystal lattice.
Iodide radical is also more nucleophilic than the other halide radicals. So we tertiary haloalkanes will react with iodides like NaI to form the corresponding iodides and sodium halides.
This is called the Coanat-Finkelstein Reaction.
{Tertiary haloalkanes will not react with the SN2 reaction meachanism, so the question of steric hinderence does not arise}
yes , but yield will be poor because of steric hindrance
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