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Attempt Since the nitrogen site is more nucleophilic it should react first. But still Oxygen can react and hence I believe A should be right. But the book says C. Where did I go wrong? Please help.

  • 1
    $\begingroup$ Well, this 100 deg. is to suggest the reaction is done is rather selective way. $\endgroup$
    – Mithoron
    Apr 26, 2020 at 18:23
  • $\begingroup$ But does temperature affect the reactivity of OH? $\endgroup$ Apr 26, 2020 at 18:40

1 Answer 1


Phenol is a pretty good leaving group so phenyl acetate is an acetylating agent and fairly labile in aqueous base. The reaction conditions are not clear enough IMO to say whether you would get a or c, but with a basic work-up the OAc can hydrolyse back to phenol. If the amount of Ac2O is limited then any PhOAc formed will acetylate the aniline giving back PhOH.

  • $\begingroup$ Why would the OAc hydrolyse? Is it that weak? Also can PhOAc undergo intramolecular acetylation of Nh2? I have never read anything like that? $\endgroup$ Apr 26, 2020 at 10:45
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    $\begingroup$ Phenol is a fairly strong acid hence its anion is stable which makes it a good leaving group. I think the transacylation is more likely intermolecular. You are on this site to learn new stuff aren't you? $\endgroup$
    – Waylander
    Apr 26, 2020 at 11:05
  • $\begingroup$ @Waylander Sir, why carbonyl group is not producing schiff bases by nucleophilic addition as it happens with aldehyde and ketones? $\endgroup$ Oct 27, 2022 at 6:17
  • $\begingroup$ Is it because medium is basic? $\endgroup$ Oct 27, 2022 at 6:29
  • $\begingroup$ Because it is not a ketone or aldehyde, it is at a different oxidation level. If you want to form an amidine you need different chemistry. $\endgroup$
    – Waylander
    Oct 27, 2022 at 8:49

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