If the 5 teeth you mentioned are adjacent teeth, then they can be removed in a single go as the number of anesthetic injections will be drastically reduced. However, if they are in different areas of the mouth, needing separate injections for each tooth, then it might be advisable to do the extractions in more than one sitting. I suggest you leave it to your dentist to make a decision depending on the clinical presentation and also on the level of cooperation of your son. But you should definitely voice your concerns so that the dentist understand what you are going through.

Usually 5 teeth should not be extracted in one sitting for a child patient,,ask your dentist to do it in 2-3 sittings.

All these queries regarding pain etc must be sought by the dentist who treat. Ok. In our center at chennai we explain all that the patients must know and the serial extraction are begun after analyzing different parameters.