Question

SN2 displacements proceed with inversion of configuration at the reacting center. Show that this is true...

SN2 displacements proceed with inversion of configuration at the reacting center. Show that this is true in the alkylation of acetaminophen using (R)-2-iodobutane in place of ethyl iodide you used in this experiment. What is the product and name?

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Answer #1

When acetaminophen (paracetamol) is alkylated using (R)-2-iodobutane, the reaction takes place by SN2 mechanism which inverts quiral carbon's configuration because 2 carbon of 2-iodine-butane is chiral. It gives 4-butoxyacetanilide

  a​nd HI

Nonetheless, if acetaminophen is alkylated using ethyl iodide, the carbon bond to iodine is not chiral and it does not invert the chiral carbon even if it takes place by SN2. Its name is phenacetin

and HI​

Its name is Phenacetin

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