4. Here's a figure-it-out mechanism, resulting in the formation of p-aminophenol from an aromatic hydroxylamine. Would you expect either ortho- or meta-aminophenol to form in competition? Why or why not? H. H;0* HO H20 ОН H.

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4. Here’s a figure-it-out mechanism, resulting in the formation of p-aminophenol from an
aromatic hydroxylamine. Would you expect either ortho- or meta-aminophenol to form in
competition? Why or why not?
H
H;0*
H
-N
НО
H2O
ОН
H
5. (a) The triaryl hydroxylamine hydrolyzes in acid to form two products: one compound
containing two aromatic rings and one with a single aromatic ring. First, draw the two products
and the mechanism of their formation in acidic water (this is another "figure it out" mechanism).
Ph
H;O*
Ph—С—N
H,0
Ph
ОН
(b) Suppose one of the aryl rings had a t-donating group (-OCH3) and the other had a n-
withdrawing group (-NO2), both in the para position. Where would the substituents end up in the
products (draw them)? Why? Do you suspect this reaction is under kinetic control or
thermodynamic control, or both/either?
Transcribed Image Text:4. Here’s a figure-it-out mechanism, resulting in the formation of p-aminophenol from an aromatic hydroxylamine. Would you expect either ortho- or meta-aminophenol to form in competition? Why or why not? H H;0* H -N НО H2O ОН H 5. (a) The triaryl hydroxylamine hydrolyzes in acid to form two products: one compound containing two aromatic rings and one with a single aromatic ring. First, draw the two products and the mechanism of their formation in acidic water (this is another "figure it out" mechanism). Ph H;O* Ph—С—N H,0 Ph ОН (b) Suppose one of the aryl rings had a t-donating group (-OCH3) and the other had a n- withdrawing group (-NO2), both in the para position. Where would the substituents end up in the products (draw them)? Why? Do you suspect this reaction is under kinetic control or thermodynamic control, or both/either?
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