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Which is more acidic, phthalimide or benzamide?

A. Predict which of the following species is the most acidic, phthalimide or benzamide. Explain.
b. What product would you expect to obtain from the reaction of one equivalent of propanol with phthalic anhydride?

Solution Preview

a) This is related to the stability of the anion that would be formed by the loss of H+. The anion formed from benzamide could potentially delocalise the negative charge ...

Solution Summary

a) The more stable anion is the one most likely to form and structures are shown in attached file. b) You may treat the reaction just like any acid + alcohol reaction. This is explained and the general reaction is illustrated in the attached file as well.

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